We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Anna Maria Holiday Vacation with Pools

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $339 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Community
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Anna Maria are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    Clear All
    1 / 40
    5 of 5 bubbles (12) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Certificate of Excellence
    Match
    All pools
    Show Prices
    Payment Protection
    1 / 39
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    1 / 23
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    1 / 17
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Grill
    • Washer
    • Wi-Fi
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Anna Maria Island, This property is located directly across from the famous Manatee County Public Beach. Groomed daily, Lifeguards, restaurants, surf shop and more.. Free trolley stops there both northbound and south every 20 minutes. The location is also right in the heart of the island. Walk to... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    1 / 32
    4 of 5 bubbles (9) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Shared Outdoor Pool...
    • Internet Access
    • Terrace
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    744 Jacaranda - Private home 3 Bedroom/ 3 Bath with private pool, maximum occupancy of 6 people. Live the Florida lifestyle in this beautiful, comfortable 3 bedroom, 3 bath private home with private pool and with screened lanai. The home is located on Anna Maria Island in the prestigious north... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 3 May 2013
    We loved this house for the week we spent in it. it was very clean and had all the little extras that make a holiday let in the U.S. ideal for a U.K. family - i.e. lots of beach...
    See all reviews
    1 / 39
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Balcony
    • Washer
    • Wi-Fi
    • Patio
    • Private Outdoor...
    • Porch
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a three houses away from the beach at Bean Point and a short walk to Rod and Reel Pier. The spacious open concept living area is perfect for spending quality time with the family. The home exudes an Island charm... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 30 January 2017
    The house is just as the pictures suggests. The floor plan was very spacious. We traveled with 6 adults (4 were college students) and there was ample room to spread out. The...
    See all reviews
    1 / 45
    4.5 of 5 bubbles (20) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Grill
    • Satellite TV
    • Balcony
    • Private Outdoor...
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 2 January 2017
    This is an excellent vacation home to spend with a large family looking for a quiet getaway on AMI. Our family of eight adults, one teenager, one toddler, and one infant spent 7...
    5 of 5 bubbles Reviewed 27 December 2016
    We've stayed on AMI many times and this house was far and above the best one we have rented on the island! Great location....can walk everywhere and gorgeous views from all of...
    See all reviews
    1 / 14
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Balcony
    • Terrace
    • Shared Outdoor Pool...
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    103 Pelican - Private canal home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. At this spacious, family friendly home with private pool, grab your fishing pole, take the hand of a child and meander to the private dock, cast a line while dangling your feet and spending the... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 17 April 2016
    Hi! My husband and I rented this property and had the wonderful opportunity of having our adult children & their spouses come with us. There was 8 of us in total. We enjoyed...
    See all reviews
    1 / 37
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other traveller has booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Private Garden
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Cast Villa #4 is the most private on this lush tropical Half acre property. Located directly across from the famous Manatee County Pubic Beach. Swim with Life guards present. Known for the pristine sugar white sand beaches. Dine early breakfast or have a beverage listening to live music daily.... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool...
    • Terrace
    • Internet Access
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    209 Spring - Private home 3 Bedroom / 2 Bath with private pool, maximum occupancy of 8 people. Spring into the waves!~ 209 Spring. 3 bedroom, 2 bath raised home in quiet, residential area of Anna Maria. Private pool. Pool heat optional * $20/day. 1 block to the beach. Large screen high def... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beachy Keen 408 - Private home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. Here delightful and fun Caribbean Cool décor welcomes you to the sub tropic cozy of Anna Maria Island. A charming island home within easy walking distance to the beach, offers an ideal location... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Secure Parking
    • Satellite TV
    • DVD Player
    • Balcony
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Newly renovated beach condo just 50 steps to the sand. Over 1200 sq ft with 2 lanais and 1 spacious rooftop deck for spectacular ocean views. Granite Counter Tops Stainless Steel Appliances Washer and Dryer Heated Outdoor Pool Beach Supplies Walking distance to restaurants and Shops Close to... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Internet Access
    • Washer
    • Patio
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The home is immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools larger backyards and larger 2 bedroom homes on the Island. The spa is accented by iridescent glass. The 20' tall tiki hut was hand-built by Native Americans and houses the bar and... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Located on beautiful Anna Maria Island, "Le Paradis" (which means Paradise in French) is just a short stroll to the sugar white sand beaches of beautiful Anna Maria Island... Experience a luxurious beach vacation with over 2100 hundred square feet of tastefully living space with an expansive... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • Satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Private Outdoor...
    • Patio
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautiful, recently renovated 1700 sf home that accommodates up to 8 people. Only a few steps to amazing sandy gulf beach. Enjoy all the amenities of a single level well appointed home with no stairs where you can step out to the beautifully landscaped pool area from your master bedroom or open... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    1 / 19
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Balcony
    • Porch
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    5 Bedroom 3 Bath Large Family Beach House Sleeps 10. Just 200 steps to the most Beautiful Beach in the World. Crystal Clear waters with plenty of fishing, wildlife and swimming. Great for Multi-Family Gatherings, Weddings, Family reunions or just plain fun. With a 2 bedroom 1 bath attached... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 28 March 2017
    Great location.We really enjoyed our stay at your home .The kids loved the pool.The home had everything we needed for our vacation.
    See all reviews
    1 / 33
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Internet Access
    • Terrace
    • Balcony
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear, from all living spaces. With 5... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 27
    4.5 of 5 bubbles (18) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Private Outdoor...
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    3 Story 'Nantucket' Style - 4 bedroom/ 3 bath villa is just a short walk to the beach - Nestled in a tropical setting, only a few blocks to the Gulf beach; private pool great for cooling off and a large sun deck. 4 Bedrooms/3 baths, large master suite with king size bed and a roman tub, 2nd... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    5 of 5 bubbles Reviewed 10 April 2017
    We rented this home over Spring Break with my brother and his family. The layout of this house is great as well as the location of the home on the island. There were 2 master...
    5 of 5 bubbles Reviewed 10 February 2017
    The location couldn't be better with an easy walk to the beach and several very good restaurants and free bus service running every half hour throughout the island. The beach is...
    See all reviews
    1 / 30
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Private Outdoor...
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautiful gem in the much coveted City of Anna Maria's north end. It is a single family home located on a quite street. Easy walk to the gorgeous white sand Bay and sugary sand Gulf of Mexico beaches with striking sunsets . With Pine Ave (our fantastic little Main St.) just a short stroll from... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 2 weeks ago
    This home really does have the "wow factor." The moment we walked through the door we were blown away. The best of everything is in this home...the kitchen appliances, bedrooms...
    5 of 5 bubbles Reviewed 2 weeks ago
    What a great trip place!! Beautiful views - accessible to everything and great outdoor living space!! Loved the morning sunrise and evening sunsets from the rooftop. Thank you...
    See all reviews
    1 / 23
    5 of 5 bubbles (9) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ahhhhhh. Welcome to Beach Nest! Ready to satisfy that oh-my-gosh-we-need-a-vacation? Kick off your shoes and throw them in the back of the closet. Promise yourselves to live in bathing suits from breakfast to bedtime! <BR>Vacationers, dreamers, honeymooners, would-be family-reunion planners and... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 24 February 2017
    Beach Nest is wonderful. Decorated with flair and beachy elegance, it feels like a home, not a rental. There is everything you need and more. You can walk to the beach with your...
    5 of 5 bubbles Reviewed 20 January 2017
    The Beach Nest is wonderful and relaxing!! The pool, the home, the cleanliness, the cuteness, and the canal were all such a treat for us! We will be back for sure!
    See all reviews
    Get the List
    1 / 23
    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • DVD Player
    • Hot Tub
    • Private Outdoor...
    • Air Conditioning
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy our Luxurious Villa diPalma, a beautiful six bedroom, four bathroom luxury island home very close to the best beach in the Northshore. The Italian influence in the design is reminiscent of properties found in Venice and Tuscany. The two master suites each have their own Jacuzzi spa tub, a... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 123
    5 of 5 bubbles (34) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Just steps to the sugar sand beaches in Anna Maria, FL. Your 3 bedroom, 2 bath, pool home with sweeping gulf views from two elevated front porches is located in the charming northern end of Anna Maria on North Shore Drive. If you are looking for a tropical vacation home to just relax, take long... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 2 February 2017
    We arrived to an obvious effort to provide for above and beyond the norm in regards to service and accommodations. A bottle of wine and fresh flowers made for a welcome...
    5 of 5 bubbles Reviewed 2 January 2017
    Vacation Island House is a charming, beautifully maintained pool home. My husband and I have been renting beach houses for over twenty years, and this is the best appointed one we...
    See all reviews
    1 / 25
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Private Garden
    • Wi-Fi
    • Private Outdoor...
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Location, location, location. If you are looking to be close to the GULF beach, this is the one. Beach Cay is perfectly situated at the very desirable North End of Anna Maria Island, just steps to the Gulf of Mexico's white sugar sand beaches (the Gulf side of the island, not the bay side!). Beach... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 42
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Outdoor...
    • Washer
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Step into an ultra private, secluded, tropical paradise with a lush canal front setting in quiet cul-de-sac located on the north end of Anna Maria Island. There is a beautiful heated pool just steps outside your door. The back yard has multiple areas to relax away the day and enjoy the amazing view... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 30 September 2015
    I chose Island Oasis as it ticked every box. This is a beautiful island and the beach is very easy to access, as such I wanted a property with a pool, suitable for two couples...
    See all reviews
    1 / 22
    5 of 5 bubbles (21) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Washer
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor...
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    4 Bedroom 5 bath luxury beach front house sleeping 8 with heated pool separate spa numerous decks and stunning beach views from every room. We are located on the desirable family friendly island of Anna Maria. The house is direct beach front on the quiet upmarket north end of the island. Recently... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 3 weeks ago
    If you are looking for a property to relax by the beach or a swimming pool, this is about as good as it gets. There is nothing the owner's have not thought about. Great ocean...
    5 of 5 bubbles Reviewed 30 April 2016
    Nigel's Anna Maria Island home was awesome from the word go. The house is meticulously maintained and looks like a new home. Everything is well organized and easy to...
    See all reviews
    1 / 23
    5 of 5 bubbles (5) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Porch
    • Parking
    • Private Outdoor...
    • Air Conditioning
    • Washer
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Please contact Sato Real Estate for booking information. Rates are subject to change. We call this home "A Time Out" cottage and you will definitely say, "We deserve a time out at this place!" This completely remodeled private home on Anna Maria Island's north end features four bedrooms, two baths... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 bubbles Reviewed 28 May 2015
    Overall, this place is beautiful! Every room is well decorated and comfortable. We loved having our morning coffee on the front porch looking at the bay. We enjoyed lunch and...
    5 of 5 bubbles Reviewed 7 April 2015
    This special house is located perfectly away from the hustle and bustle, but at the same time everything is easily accessible. The beautiful beach is just a short stroll, and...
    See all reviews
    1 / 50
    4.5 of 5 bubbles (10) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Private Outdoor...
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Upscale luxury executive four bedroom waterfront home with private pool dock and elevator. Stylishly furnished and dressed, modern build 2006 - this is our family second home - and is home from home available to you. This exclusive executive property is in the heart of lovely Anna Maria... View all property information
    Location Information
    Anna Maria, Anna Maria Island FL34216
    5 of 5 bubbles Reviewed 27 February 2017
    Bayview Dream did not disappoint! It truly was a dream holiday for us. The house itself is beautifully decorated and very well equipped - plenty of towels (indoor and pool...
    4 of 5 bubbles Reviewed 17 January 2016
    We spent a week in this lovely home. The weather was cool, so we didn't use the pool, but there was a beautiful pool with a dock right out the back door. The home was spacious...
    See all reviews
    1 / 41
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Satellite TV
    • Private Outdoor...
    • Grill
    • Internet Access
    • Air Conditioning
    • Parking
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to a true Anna Maria Island treasure! Bimini Bay is an irreproachable 4 bedroom, 3 bath ground-level home tucked away on the quiet north end of Anna Maria. Previously a duplex, both units were completely gutted and combined to bring you this gorgeous 4 bedroom home with its own private... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 29 October 2016
    Just got back from a girls trip with five friends at Bimini Bay. The house was PERFECT. Bright, clean, fresh, comfortable, and super cute. The pool and outdoor seating areas were...
    See all reviews
    1 / 39
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Hot Tub
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to Canal Place, an inculpable island home that is outfitted to offer occupants an unforgettable vacation experience! In your privately cultivated backyard is an assemblage of accessories providing plenty of options for fun in the sun. There is a heated pool, hot tub, kayaks, boat dock,... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 41
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Grill
    • Parking
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This adorable remodeled duplex sits quietly in the highly desirable north end of the Island in the City of Anna Maria. It is a short walk of only a little more than a block to the Gulf beach where the sand is sugary white and the water is a beautiful blue-green color. There is a King in the master... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 33
    4 of 5 bubbles (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Parking
    • Grill
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 bubbles Reviewed 13 January 2016
    This was our first time on the island. This house is a short 5 minute walk from a fabulous beach, and you share a pool with the other side of the duplex. The neighbourhood...
    5 of 5 bubbles Reviewed 8 June 2015
    The cottage was just as the picture depicts. It was close to the beach and we only had to worry about 1 other rental on the property. A lot of privacy and all the amenities...
    See all reviews
    1 / 39
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Grill
    • Private Outdoor...
    • Waterfront
    • Hot Tub
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Situated on an enormous lot within the quiet north end of Anna Maria, you will find this treasure of a vacation home. Fins Up is a uniquely perfect 3 bedroom, 2.5 bath home with its own private pool, hot tub, 2 docks, and fully enclosed spacious outdoor shower. Privacy fenced is the huge backyard... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 35
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Grill
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Outdoor...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Looking for that place to kick back and relax your cares away? Check out ‘Triple Play Guest House.' There's a triple chance to play: (1) walk to the beach, (2) lounge in the pool or spa or patio or (3) launch a kayak, fish or just relax on one of our two docks on the canal. Nothing quite compares... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 24 June 2015
    This house is nothing less than spectacular for a family. The house has been completely redone inside. The house looks very small from the front / driveway, but the inside is...
    See all reviews
    1 / 30
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Grill
    • Washer
    • DVD Player
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 42
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • Private Outdoor...
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Inspired by modern Italy, North End Zen's sleek and minimalistic touches throughout will at times have you feeling as you were vacationing on a posh Mediterranean island. The spacious open concept floor plan begins at the front door and gracefully moves its way to the back of the house which has... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 37
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor...
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a short walk to the beach, bean point, and the Rod and Reel Pier. The spacious open concept living area is perfect for spending quality time with the family. The home exudes an Island charm with its over 2000... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 40
    3 of 5 bubbles (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Air Conditioning
    • Parking
    • Satellite TV
    • Wi-Fi
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful ground level 3 bedroom/2.5 bath home, with a quiet north end location only a block to the beach! There is a King in the master with a private patio, a Queen in the second, twin beds in the third, and a queen sleeper sofa in the sunroom (which has blinds for privacy), all accommodating up... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    3 of 5 bubbles Reviewed 1 July 2014
    We had a great time on Anna Maria with our two college-aged sons. This house is very nicely located, and the pool is wonderful. The home was spacious and comfortable for four...
    See all reviews
    1 / 40
    4.5 of 5 bubbles (6) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Washer
    • Private Outdoor...
    • Internet Access
    • Patio
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautiful, cheerful and tropucal 4 bedroom/2 bath home with beautiful new furnishings throughout! Quiet surrounds yet just a few steps from Pine Avenue shops and restaurants. One block away from free trolley. Comfortable and roomy with split floor plan (two bedrooms on each side!). The living room... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 35
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Grill
    • Private Outdoor...
    • DVD Player
    • Satellite TV
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Toes in the Water is an amazing ground level 4 bedroom/3 bath home, just 90 Steps to the beach! This north end gem boasts a large, private, and heated pool with swim-up tiki table. Quiet setting in the beautiful north end of Anna Maria, and located west of Gulf Drive for easy beach access with no... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 27 October 2013
    My parent rented this house when they came to visit last winter. We stayed for a week in late January(?) to early Feb and my 3 year old son still asks to go back. Personally I...
    See all reviews
    1 / 39
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Grill
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to the exceptional beach house that is Blue Turtle! This 4 bed/3 bath gem is perfectly positioned on the north end of Anna Maria and will positively provide a picturesque vacation experience. The gorgeous backyard is your private, tropical paradise complete with heated pool and dock to take... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 29
    4 of 5 bubbles (7) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Private Outdoor...
    • Washer
    • Balcony
    • Porch
    • Satellite TV
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Cherryfish is the latest addition to the Pineapplefish collection of houses on Anna Maria Island. It is a spectacular 4 bedroom house, in a fantastic location, just one block from Tampa Bay Beach, the amazing Waterfront Restaurant and the island's most popular tourist destination - City Pier.... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 24 May 2016
    We are a family with young children and thoroughly enjoyed staying at this property. There was plenty of space and bathrooms for all and the pool was a great hit with everyone...
    3 of 5 bubbles Reviewed 13 April 2016
    Let me start by saying this place is stunning. We walked around the island a lot and this is without doubt one of the most impressive looking homes on Anna Maria. It's just a...
    See all reviews
    1 / 39
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Washer
    • Wi-Fi
    • Grill
    • Patio
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    When you 'have anna maria' on your mind, you'll want 'hav'anna hideaway' for your vacation home. This 4 bedroom, 4 bath home is located just one short block to the beautiful and sparkling gulf beach. The main floor of the home consists of an open concept living room, kitchen with breakfast bar... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 27 August 2015
    This property was everything we had hoped for and more! Centrally located in one of the best parts of Anna Maria Island, and even though it was close to one of the main streets it...
    See all reviews
    1 / 29
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Terrace
    • Wi-Fi
    • Washer
    • Balcony
    • Parking
    • Grill
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This great 2 Bed/2 Bath Home with Private Heated Pool resides in Anna Maria and is only one block to the beach and has no busy streets to cross to get there. You can quickly make your way to the Gulf Sands and to all of the great shops and restaurants that Anna Maria and Holmes Beach have to offer.... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 25
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Private Outdoor...
    • Grill
    • Washer
    • Patio
    • DVD Player
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Great Ground Level 3 Bedroom/2 Bath Home with a Heated Pool located in the quiet north end and just 3 houses to the beach!! King-Sized master bedroom with TV, Queen in the 2nd Bedroom with TV, and Twins in the Third with TV. Cable TV, DVD, and Flat Screen TV in Living Room. High speed Internet,... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 40
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Air Conditioning
    • Washer
    • DVD Player
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Lazy Lagoon has it all! This remodeled 2 bed/2 bath home is anchored in splendid the north end of Anna Maria on a deep water canal with dock, has its own heated pool and hot tub, and is a short walk to the beach, restaurants and free island trolley. The serene canal-front setting coupled with quiet... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 13 January 2014
    We have just come back from a 2 week stay at Lazy Lagoon. House beautiful, all on one level and flooded with light. Pool and hot tab a fantastic feature. House fully equipped and...
    See all reviews
    1 / 40
    4 of 5 bubbles (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor...
    • DVD Player
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located in the heart of Anna Maria, a gorgeous and spacious Mediterranean style 4 Bedroom/3 Bath Home with a Heated Pool in a very private and peaceful setting. Only steps to Pine Avenue shopping and Trolley Stop, 2 blocks to the Beach, and walking distance to the Pier. The open floor plan features... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 34
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Patio
    • Satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This adorable remodeled duplex sits quietly in the highly desirable north end of the Island in the City of Anna Maria. It is a short walk of only a little more than a block to the Gulf beach where the sand is sugary white and the water is a beautiful blue-green color. There is a King in the... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 17 January 2016
    A great 2 bedroom duplex with a waterfall pool,on the northern part of Anna Maria Island. Walking distance to the beach (2 blocks). The rental was clean and well maintained, the...
    5 of 5 bubbles Reviewed 3 September 2015
    Stayed here for a week. Nice apartment, clean and useful accomodation. Any small issues were sorted really quickly by agent who was very helpful and only 2 mins away in...
    See all reviews
    1 / 40
    5 of 5 bubbles (7) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Satellite TV
    • Grill
    • Wi-Fi
    • Private Outdoor...
    • Patio
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beachcombers is a spacious 3 bedroom/2 bath home with all of the "Old Florida Charm" you could ask for. Situated on Spring Avenue, just a couple of blocks to the Gulf of Mexico on Anna Maria's beautiful north end! Easy walking distance to many shops, restaurants, the Anna Maria City Pier and a... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 5 weeks ago
    The beautiful backyard with pool, refreshing cross breeze in the house, front deck, well equipped kitchen and quiet yet close location were all wonderful. We loved that there...
    5 of 5 bubbles Reviewed 6 September 2016
    We had a fabulous holiday during our 7 night stay at Beachcombers in June 2016. The villa was beautifully decorated with its bright fresh colours and beach house theme. The well...
    See all reviews
    1 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Patio
    • Private Outdoor...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beach Baby is situated on the north end of Anna Maria and is only 4 houses to the gorgeous Gulf waters that the Island is famous for. This great two story house offers a private Heated Pool with Hot Tub and two hammocks on which you can take in the island sun. The main living level contains the... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 33
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Match
    All pools
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Washer
    • Internet Access
    • Patio
    • Grill
    • DVD Player
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautifully redone 3 bedroom/2.5 bath home! Ceramic tile throughout, and brand new open kitchen area with breakfast bar. Beautiful large caged pool area with huge covered patio! Only a block to the beach, the Sandbar Restaurant, Ginny and Jane E's, Rudy's Subs, Feeling Swell and more. Just a... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 3 November 2016
    Beautiful home. 1 block to the Gulf, restaurant and music on the beach. Free breakfast, on Sunday, at Harry's Restaurant on Gulf Blvd. Music, shopping, and the sunsets! Wow. Child...
    See all reviews