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 Cheap Vacation Rental Deals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    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}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    C$168 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Travellers to Anna Maria are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    47 Matching Rentals in Anna MariaView all 190 rentals
    Sort by:
    Price (Low to high)
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Little Slice of Paradise: Very Nice Canal-Front Condo on Historic Pine Ave!1 / 24
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Parking
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 11, 2017
    This Apartment was perfect for us. Very clean and a great location on Pine Avenue. We were early but the apartment was ready. Great having a balcony as well. So peaceful sitting...
    Reviewed October 26, 2015
    We love Anna Maria! This 2 bedroom condo was ideally located right on the canal, which is right off Tampa Bay. We were able to drop our paddle boards or kayaks right off the...
    See all reviews
    About this property
    Located on the north end of Anna Maria Island in the city of Anna Maria on historic Pine Avenue, this two-bedroom, one-bathroom second-floor vacation rental condo has been completely updated and is picture perfect. So much so, once you walk through the front door you'll feel as though you just...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    19 Palms. Quaint Old-Florida Charm1 / 23
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Washer
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 4, 2018
    My husband and I come to Anna Maria Island annually and always stay here. It’s spotless, beautifully decorated, ultra comfortable beds and new shower heads. The location...
    Reviewed March 4, 2018
    The location of the house is close to the beach and you can also walk to all the shops and dinning or bike ride. Parking is right at the doorstep and it is on a quiet street...
    See all reviews
    About this property
    This quaint, old-Florida style rental is nestled in the north shore area of Anna Maria Island. Shabby chic style, located 2 blocks from the beach and 2 blocks from the bay! Only one block from Pine Ave., with its old-time feel with shops and salons. Steps from fine dining, the historic city pier,...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Parking
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute one bedroom/one bath with open floor plan and adorable furnishings and now featuring our professional linen service! Colorful decor and beadboard accents adorn the unit. There is a queen sized bedroom with flat screen TV and sliders going out to an outdoor deck and sitting area. This...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7201 Palm Drive, Holmes Beach, Anna Maria Island Palm Cottage ... Lovely 2 bedroom, 2 bath recently updated home. This ground level home offers a beachy decor, a new pool , granite countertops, and a great screened in porch. Just a short walk to the beach. Pool heat is additional....
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Enchanted Cottage: Renovated Historical Anna Maria Cottage. Cute & Pet Friendly!1 / 24
    (2)Average
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, quiet, cozy, Enchanted Cottage is just steps to Tampa Bay and the Historic Anna Maria City Pier, a fun place to fish! A short five blocks to the beautiful powder-soft, white sand and turquoise Gulf water of Anna Maria Island. You may also enjoy the beautiful sunrise from the pier...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
    Make Enquiry
    Ocean View 3 bedroom, pool, North Shore Drive1 / 123
    (37)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 2018
    We had a wonderful, relaxing time while staying at this terrific house! First of all, the house was very clean and very well kept by the owner. There also is lots of...
    Reviewed November 5, 2017
    Great place I had my birthday party here it was so fun Very close to the water every thing was to the t in cleanliness sleep 6 of us it was all around one of the best beach...
    See all reviews
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tastefully decorated with an island flair! The White Egret has furnished and decorated this adorable two bedroom/one bath half duplex on the north end of Anna Maria Island! The master bedroom has a king sized bed, with sliding doors out onto a deck area, and the second bedroom has a queen sized...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Save time - get the best Anna Maria rentals sent straight to your email!
    Get the List
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Central Heating
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ibis unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Cast Villa 11 / 31
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Washer
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 3, 2017
    Was absolutely wonderful. Couldn't ask for better vacation. Very close to beach. Unit had everything we needed. Owner was very friendly and accomidating. Will definately be back.
    See all reviews
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Ocean Views
    • DVD Player
    • Central Heating
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anna Maria Island is still old Florida, I am on a half acre of very Tropical Palms and landscaping. Located in the heart of the Island. Directly accross from the Famous Manatee County Public Beach. Reasturants, Free trolley all right there. Also grocery, pharmacy, shopping within walking distance....
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    A Place in Paradise A: Just Two Blocks From The White Sand Beaches Of Anna Maria1 / 23
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 31, 2018
    We have been coming to Anna Maria for a while, and for obvious reasons, the island is becoming very popular. Inevitably, this has made rentals at a reasonable price tough to...
    Reviewed December 30, 2017
    The condo was perfect for our family getaway . The amenities, location, and fully stocked kitchen were everything needed for a perfect holiday gathering.The location is within...
    See all reviews
    About this property
    We have a place in paradise waiting for you! This Anna Maria Island vacation rental is located in Anna Maria and is just a short two block walk to the white sand beach of the Gulf of Mexico. A nice living area with flat screen television is great for relaxing after a day at the beach! A nice...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    A Place in Paradise B: Just Two Blocks From The White Sand Beaches Of Anna Maria1 / 23
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 20, 2018
    1st of all very spacious rooms, plenty of smallwares in kitchen, great kitchen and do not forget the outside Grill. My kids really appreciated all beach accessories and...
    Reviewed May 31, 2018
    I can truly say I will be back. This beach condo is conveniently located two blocks away from the beach is one of the reasons that made it special. Also in the area are a...
    See all reviews
    About this property
    We have a place in paradise waiting for you! This Anna Maria island vacation rental is located in Anna Maria and is just a short two block walk to the white sand beach of the Gulf of Mexico. A nice living area with flat screen television is great for relaxing after a day at the beach, while a nice...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Charming cottage w/ island views, entertainment & nearby beach access!1 / 33
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Internet Access
    • Patio
    • Parking
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 29, 2018
    If your looking for a laid back beach cottage in a laid back beach community this is it. Little delay getting in the door because the key pad didn’t work, but once I stepped...
    See all reviews
    About this property
    A dose of sunshine and relaxation awaits you at this comfortable cottage on Anna Maria Island, featuring island views, entertainment, and easy access to the beach. Located immediately east of Gulf Drive, a quick 200-yard walk will bring you right to the white-sand beach and crystal-clear waves. Go...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Anna Cabana B: North End Pool Home just a short walk from the beach!1 / 24
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Internet Access
    • Grill
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 1, 2016
    This modern beachy cozy home was absolutely gorgeous! Clean, and equipped w/ all the modern, brand new, full size amenities. Beachy/luxury design. Central air & on-site...
    Reviewed January 8, 2016
    I enjoyed my vacation in this beautiful house very much. The furniture is very nice and comfortabel and the entiere house is beautiful decorated. It provided everything what I...
    See all reviews
    About this property
    Anna Cabana B is the perfect getaway. Located on the north end of Anna Maria Island and just a short walk from the beach, this cute bungalow beckons you to relax and stay a while! This adorable island vacation rental has been completely refurbished inside and out! A queen bedroom and a sofa bed...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Washer
    • Cable/satellite TV
    • Balcony
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ibis unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Internet Access
    • Grill
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Gladiolus House and what a location, north of Pine Avenue! An old style florida two bedroom/two bathroom cottage on the north end of the Island! Not enough room for all the family, Gladiolus House is right behind Hibiscus House so why not rent both properties to accommodated...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the north end of Anna Maria Island, Bay Bungalow is less than two blocks from popular and secluded Bean Point beaches. This family-friendly destination offers a heated pool, a game console, Ping-Pong, foosball, and bikes for cruising around on island time. What’s nearby: Just a block...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Parking
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Savor your time on Anna Maria Island with a stay at this whimsical one-level cottage! With room for everyone to enjoy a slower and mellower pace, you’ll be living like a local in no time. 

 Take a ride on the island’s free trolley to explore the sugar sand beaches (Palmetto Avenue Beach/City Park...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Say goodbye to stress and hello to island vibes at this spacious beach house. Featuring a private yard with tropical greenery, a dog-friendly attitude, and a great location near the beach and pier, this house will have you living in a dream! Sitting near the northern tip of Anna Maria Island, this...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This two bedroom, two bathroom beach cottage is so close to the beach you can smell the salt air! That's especially true on the spacious patio, where you can relax, dine al fresco, and grill out. The family dog is also welcome here for a small nightly fee. The beach's sugary sand is right at the...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Washer
    • Grill
    • DVD Player
    • Air Conditioning
    • Terrace
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sandy’s Getaway offers two distinct spaces to accommodate the whole family or multiple couples - a ground-level bedroom and a larger upstairs suite, connected by outdoor stairs. Everyone is welcome here, and that does include the family dog! Canine members of the family, up to 30 lbs, are welcome...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Island Place Cottage: Beautiful Pet-Friendly Cottage On Historic Pine Ave!1 / 23
    (9)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 11, 2018
    We decided to go to Ana Maria Island over Christmas 2017 because this was the year we had to share our grown and married children with their in-laws. We had never vacationed...
    Reviewed June 29, 2017
    Great location with shops and restaurants within walking distance. The two piers are also just a short walk away. The cottage is basic but very clean, an ideal base for a few...
    See all reviews
    About this property
    This vacation rental is located on Anna Maria Island's historic Pine Avenue, halfway between the Gulf of Mexico and the Anna Maria City Pier! This adorable, one bedroom cottage, with high beamed ceilings, wood floors and shabby chic décor throughout is ideal for a vacation getaway! This quaint...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Parking
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    604 North Shore, Anna Maria Island, Fl 34216 Unit 2 'Still Water'... Adorable, vintage 1 bedroom cottage on Lake La Vista located at the north end of the Island . Just 250 steps to the beach and just a short stroll to historic Pine Avenue for great shopping. Exceptional, 'Old Florida' charm!...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Grill
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Salt Box Cottage is newly renovated, bright, clean, cozy and the perfect place for an Anna Maria Island vacation. This quaint vacation rental cottage is just steps to Tampa Bay and five blocks to the beautiful powder-soft, white sand beach and turquoise water of the Gulf of Mexico! Accommodations...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Paradise at the Bayou1 / 20
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Patio
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 7, 2018
    We loved staying at Greg and Lori's condo. Just as shown on site, hosts provide everything needed to enjoy vacation in their place including kayaks, beach chairs, towels etc as...
    Reviewed June 7, 2017
    The rental was extremely clean and well stocked with all the amenities needed for cooking, fishing, sitting on the beach or just reading a book while watching the fish jump. The...
    See all reviews
    About this property
    This water front, two bedroom condominium (ground floor), sits on the end of Pine Avenue, across the street from the beach and has wonderful seaside views of the bay. It also has its own private fishing dock and boat slip! This unit has been completely remodeled and newly furnished to give you the...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • DVD Player
    • Internet Access
    • Patio
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched on the coveted northern end of Anna Maria Island, this charming and recently updated beach cottage offers three bedrooms and two bathrooms, three parking spots, and a fabulous location just two blocks from Bean Point Beach. You can even bring your dogs! (50 lbs. max, please - a small...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Casa Palma: Absolutely  Gorgeous Family-Friendly Pool Home In Anna Maria!1 / 23
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 29, 2017
    The house was beautifully decorated but a little on the older side could have been cleaned better a lot of dust and the pool was small and not cleaned the entire time we were...
    Reviewed March 14, 2017
    We rented this wonderful house for two weeks, two years in a row. Tried to rent it this year but couldn't find it. Perhaps they switched to a new rental company?This is a...
    See all reviews
    About this property
    If you are looking for the perfect spot to vacation on Anna Maria Island, look no further! This beautiful Anna Maria vacation rental is fabulously decorated throughout! Open and airy, with a fantastic living area, Casa Palma has plenty of room for all of your family and friends. The gourmet...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Grill
    • Washer
    • Internet Access
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for the picture-perfect spot to vacation on Anna Maria Island, look no further! This beautiful Anna Maria vacation rental is spectacularly decorated throughout! Open and airy, with a fantastic living area, Villa Palma has plenty of room for all of your family and friends. A...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Air Conditioning
    • Grill
    • DVD Player
    • Patio
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Holly Hideaway, tucked away between palms on the beautiful northern end of Anna Maria Island. Enjoy tropical breezes wafting through the screened lanai and across the patio and upstairs balcony while you grill out or take a dip in the heated pool. Beautifully furnished, this home and its...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Gulfshore Cottage: Lovely Family-Friendly Home, Just 1 Block from Beach!1 / 24
    (24)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Washer
    • Parking
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 7, 2017
    I was lucky enough to secure another stay, my third at this wonderful cottage.Every facility that you would need is available within the cottage . Well stocked for your beach...
    Reviewed November 6, 2017
    This is our third stay at the cottage, and our favorite place to stay when we visit Anna Maria island. It's tough to beat the location, being just a short walk to the beach...
    See all reviews
    About this property
    Your time on Anna Maria Island should be perfectly charming in this classic three-bedroom beach-style cottage perfectly located on the west side of Gulf Drive in the city of Anna Maria. Only steps away from the azure blue waters of the Gulf of Mexico, this unique vacation rental boasts two very...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Washer
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Pier House! What a location and north of Pine Avenue! An old style florida three bedroom/two bathroom cottage on the north end of the Island! Pier House is right around the corner from the Rod and Reel Pier where you can enjoy the famous grouper sandwich. The Cottage is a short walk...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Terrace
    • Balcony
    • Grill
    • Washer
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minnow 2  is a ground level, beautiful, tastefully decorated, polished terrazzo throughout, two bedroom, one bathroom bungalow offering a secluded and private screened in patio! It is only a short 2 minute stroll over to the beautiful white sandy beaches and a 45 second walk to the Rod and Reel...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    313 Palm Ave - Duplex 2 Bedroom /1 Bathroom , maximum occupancy of 4 people. Distance to the Beach: 5 min walk Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 5 min walk from the beach! Located right in the heart of the village of Anna Maria, not only can you walk to...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Internet Access
    • Grill
    • DVD Player
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Chase sunsets and island vibes at this lovely beach house on Anna Maria Island. Offering a private heated pool, dog-friendly attitude, and access to a beach nearby, this house will ease you into vacation mode in no time! Located just over half a mile from the beach at City Park and a free trolley...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Washer
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adorned with shades of blue reminiscent of the waters surrounding Anna Maria Island, this charming cottage is a dream vacation home. Perched less than 200 steps from the beach, you're just a sea shell's throw away from Anna Maria's beautiful shore, and you have a heated pool oasis in your own...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • Patio
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come live the island life when you stay in this charming 'Old Florida' style cottage with a private pool and close proximity to the beach. You'll also have room for three cars in the roomy carport and access to Anna Maria's free trolley. With only one house between you and the glittering quartz...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Balcony
    • Parking
    • Internet Access
    • DVD Player
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll be able to spot this adorable mint-green bungalow from down the street! This charming home's dazzling location backs up to the bay with wide-open views of the waves. Keep an eye out for dolphins from your deck and balcony, or bring a book out to the beach chairs and stick your toes in the...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Anna Cabana A: North End Private Pool Home Just A Short Walk To The Beach!1 / 24
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Patio
    • Grill
    • Parking
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 2, 2016
    My husband and I spent a very pleasant two weeks at this cottage in April. It is bright, clean, comfortable (if you like a hard bed) and quite well equipped. The only things...
    See all reviews
    About this property
    Anna Cabana A is the perfect getaway! Located on the north end of Anna Maria Island and just a short stroll to the beach, this cute bungalow beckons you to stay and relax. This adorable vacation rental has been completely refurbished inside and out! A queen bedroom and a full bunk with twin over,...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Tequila Sunset:Great Island Home With A Private Heated Pool!1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Washer
    • Cable/satellite TV
    • Grill
    • Parking
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 17, 2015
    We saw this rental a year or so ago when we were staying on Anna Maria Island. We looked it up on line and was happy with what we saw. The home sleeps a family of four. It was...
    See all reviews
    About this property
    Begin your Tequila Sunset vacation in this lovely vacation rental that is just a few houses from the white sand beaches of Anna Maria Island! Once inside, an island cottage feel will surround you with an open floor plan, lively colors, and wood floors. This two-bedroom, two-bath home features a...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come discover 'Paradise Cottage' with all it's old Florida charm as well as newly updated appliances and decor.  This lovely and colorful two bedroom, two bath home feels brand new.  You'll enjoy tile floors throughout, a large eat-in kichen, comfortable and attractive furnishings with an updated...
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property
    Owner log in