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House Rentals in Anna Maria Island, FL

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    All 962 Rentals in Anna Maria Island
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    Travellers to Anna Maria Island are booking March dates now. Secure your vacation rental today, and have the perfect trip.
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    From
    $440
    / Night
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    1 / 26
    5 of 5 stars (3) Excellent
    Anna Maria
    3 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Reviews (3) Make Enquiry
    From
    $629
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    1 / 26
    5 of 5 stars (1) Excellent
    Anna Maria
    4 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Reviews (1) Make Enquiry
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    $315
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    1 / 22
    4 of 5 stars (1) Very good
    Anna Maria
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    From
    $415
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    1 / 24
    5 of 5 stars (1) Excellent
    Anna Maria
    5 Bedrooms / 3 Bathrooms / Sleeps 14
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    Amenities & Details
    • Dishwasher
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Villa Del Sol 211 Chilson Avenue Anna Maria, FL 34217 This is an exquisite, newly remodeled 5 bedroom, 3 bath ground level home with available boat dock. Inside the home you will find quality furnishings with a Caribbean decor. The open floor plan provides the perfect space for spending... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $277
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    1 / 20
    Holmes Beach
    3 Bedrooms / 8 Bathrooms / Sleeps 6
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ** VACATION YOUR WAY - this property welcomes SATURDAY TO SATURDAY reservations ** Gorgeous Gulf views located at 202 38th Street, Holmes Beach, Anna Maria Island, FL-- (3) Bed: (3.5) Bath: Accommodates up to (6) people: King, Queen & 2 twins: Internet - Wireless: No smoking: No Pets.... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $624
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    1 / 24
    4.5 of 5 stars (7) Very good
    Anna Maria
    5 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Sauna
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • Private Outdoor...
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located on the north end of Anna Maria Island in the city of Anna Maria, this family-friendly vacation rental was built for rest and relaxation. Beginning with the lush landscaping that meets you at the front door, all the way through to the putting green, kayak launch and boat dock, this house has... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $252
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    1 / 21
    5 of 5 stars (1) Excellent
    Anna Maria
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Limelight 771 Jacaranda Rd. Anna Maria, Fl. 34216 Limelight is a gorgeous newly renovated home, inside and out, located on the prestigious North End of Anna Maria Island. Only a brisk 3 minute walk away from the sandy white beaches, this home offers everything you are looking for in an Island... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    From
    $269
    / Night
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    1 / 24
    4.5 of 5 stars (3) Very good
    Anna Maria
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Stereo System
    • Private Outdoor...
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Deck
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Located in the city of Anna Maria on the north end of Anna Maria Island, this gorgeous three-bedroom dog-friendly vacation rental is the perfect place for a vacation retreat! With an estimated 2100 square feet, AMI Retreat has plenty of room to kick off your flip flops and enjoy your down time.... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    From
    $268
    / Night
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    1 / 25
    5 of 5 stars (1) Excellent
    Holmes Beach
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Dryer
    • Air Conditioning
    • Washer
    • DVD Player
    • Wi-Fi
    • Private Outdoor...
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Palm Villa is a New England-style cottage and a Florida Keys getaway all rolled into one, but located on beautiful Anna Maria Island! Just a short five-minute stroll to the white sand beach and azure blue water of the Gulf of Mexico, this home and location will bring you back time and again. The... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $198
    / Night
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    1 / 25
    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Deck
    • Wi-Fi
    • Satellite TV
    • Washer
    • Air Conditioning
    • Patio
    • Dryer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Let the 'Good Times' roll at this original and fun vacation home! The location is excellent, just a few blocks to the white sand beaches of Anna Maria Island! This fantastic, three bedroom, two bath vacation rental offers everything you need for a relaxing getaway. There are two family areas, both... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    From
    $161
    / Night
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    1 / 24
    5 of 5 stars (5) Excellent
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Dryer
    • Satellite TV
    • Washer
    • Deck
    • Wi-Fi
    • Private Outdoor...
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This elevated vacation rental offers all the modern conveniences while instilling tranquil island flair. Located in Holmes Beach on Anna Maria Island, Southern Comfort is a two-bedroom, two-bath home that sleeps four. Tastefully decorated in beach décor with hardwood and tile floors throughout,... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $220
    / Night
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    1 / 24
    5 of 5 stars (3) Excellent
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Stereo System
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Elevator/Lift access
    • Waterfront
    • Water Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    You will definitely be dreaming about the beach when you walk into this open and well-appointed two-bedroom elderly- and family-friendly Holmes Beach condo. Whether you are relaxing watching dolphins and sunsets from your private balcony overlooking the Gulf of Mexico or taking a dip in the large... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $278
    / Night
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    1 / 24
    4.5 of 5 stars (5) Very good
    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Dryer
    • Private Outdoor...
    • Washer
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Bring your tanning oil when vacationing in this gorgeous and luxurious Mediterranean style home. Boasting three bedrooms and three baths, there is room to bring the whole family for a dream vacation on Anna Maria Island. Just a mere block and a half to the white sand beach or steps to the private... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $135
    / Night
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    1 / 20
    5 of 5 stars (7) Excellent
    Holmes Beach
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Dryer
    • Washer
    • Wi-Fi
    • Satellite TV
    • Patio
    • Refrigerator
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    At first glimpse, Happy Heron will make you smile! Just one short block away from the pristine water of the Gulf of Mexico and Anna Maria Island's gleaming white sand beaches, this one-bedroom, one-bath vacation rental has been completely remodeled inside and out for your vacationing pleasure.... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $252
    / Night
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    1 / 27
    4.5 of 5 stars (9) Very good
    Holmes Beach
    3 Bedrooms / 8 Bathrooms / Sleeps 6
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Parking
    • Dishwasher
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Newer three bedroom, three and a half bath vacation beach townhome on beautiful Anna Maria Island. Enjoy a huge master bedroom with a Jacuzzi tub and separate shower. There is also a door to a bathroom that allows you to walk from the pool area through the shower for easy rinsing off and then... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $296
    / Night
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    1 / 24
    4.5 of 5 stars (7) Very good
    Holmes Beach
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Private Outdoor...
    • Dryer
    • Satellite TV
    • Washer
    • Stereo System
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This four-bedroom pet-friendly vacation rental with a heated pool is just a block to the white sand beaches of Anna Maria Island and the Gulf of Mexico. Located in Holmes Beach, Beautiful Villa by the Sea offers an open floor plan with plenty of space to accommodate 10. On the main floor you will... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $161
    / Night
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    1 / 22
    4.5 of 5 stars (10) Very good
    Holmes Beach
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (10) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Washer
    • Wi-Fi
    • Patio
    • Private Outdoor...
    • Dryer
    • Deck
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    **SPECIAL** Receive $100 off weekly rentals through July 31, 2015! To take advantage of this offer use the promo code HIDEAWAY when reserving Island Hideaway East! ------------ Island Hideaway East has been newly renovated for your vacation pleasure! Over 800 square feet of living area boasts a... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $215
    / Night
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    1 / 24
    5 of 5 stars (1) Excellent
    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Washer
    • Deck
    • Dryer
    • Private Outdoor...
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This elevated vacation rental has been newly renovated to meet your high standards of vacation home living. With over 1400 square feet of living space, this home boasts three large bedrooms with a king master suite, a queen in the second bedroom, and a twin in the third. A queen sofa bed in the... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $332
    / Night
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    1 / 24
    4.5 of 5 stars (5) Very good
    Holmes Beach
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Private Outdoor...
    • Stereo System
    • Satellite TV
    • Deck
    • DVD Player
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This beautifully furnished four-bedroom, 3.5-bath vacation rental is just a little more than a block to the beach! With a large great room layout and balconies in the front and back there is plenty of room for vacationing in this Anna Maria Island home. The master bedroom on the main floor has a... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $131
    / Night
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    1 / 28
    Anna Maria
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Wi-Fi
    • Washer
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Canary Cottage has 2 bedrooms plus a bunkroom - and 2 full baths and will Sleep up to 8. Located in the heart of Anna Maria City- This Key West charmer is elevated and has been updated with new tile, fixtures, plus a new tub/shower! Updated furnishings, and appliances, which add to the charm... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    From
    $323
    / Night
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    1 / 24
    5 of 5 stars (6) Excellent
    Holmes Beach
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Washer
    • Deck
    • Wi-Fi
    • Private Outdoor...
    • Dryer
    • DVD Player
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This beautifully-decorated Anna Maria Island vacation rental with a heated pool in a gorgeous tropical setting, a large deck and plenty of seating is just the place to stay on vacation. Strikingly furnished throughout by AMI-based Egrets Landing, Egret's Nest boasts four bedrooms and 2.5 baths to... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $157
    / Night
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    1 / 15
    4 of 5 stars (1) Very good
    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Hawaiian Tide 206 81st Street Unit B Holmes Beach, Fl 34217 Hawaiian Tide is a brand new ground level private duplex with a private heated pool! With tropical landscaping throughout the backyard and pool area you will feel as if you are transported to your own personal island. Centrally... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $189
    / Night
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    1 / 18
    5 of 5 stars (1) Excellent
    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Patio
    • TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Island House 306 A 56th Street Holmes Beach , FL 34217 For true Southern Living and if only the best will do, this beautiful island vacation home has a large private pool that is electrically heated to ensure year round warm water to swim in surrounded by gardens landscaped with tropical trees... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $152
    / Night
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    1 / 24
    4 of 5 stars (2) Very good
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Dryer
    • Washer
    • Fireplace
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Launching your kayak at sunrise from the canal dock of this gorgeous two-bedroom, two-bath home is a fantastic way to start your vacation on Anna Maria Island. Located on one of the many Holmes Beach canals, this tropically-lush landscaped vacation rental, just three short blocks to the pristine... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $140
    / Night
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    1 / 19
    Holmes Beach
    3 Bedrooms / 7 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to North Beach Village unit 27 on beautiful Anna Maria Island. This great location offers the perfect spot to walk to the beach or to shopping and dining in Holmes Beach. This town house features a 3 bedroom 2 ½ bathroom and an updated designer features throughout. There is a large screened... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $252
    / Night
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    1 / 25
    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Waterfront
    • Shared Tennis Court
    • DVD Player
    • Air Conditioning
    • Water Views
    • Elevator/Lift access
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Once you open the door to this Gulf View, you will begin to relax. Restful and soothing beach colors throughout this two-bedroom, two-bath condo will encourage you to have a fabulous vacation on Anna Maria Island. The breathtaking view of the sparkling water through floor to ceiling windows in the... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $440
    / Night
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    1 / 27
    5 of 5 stars (1) Excellent
    Holmes Beach
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • TV
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Avalon 2803 Ave E Holmes Beach, Fl. 34217 Wow, if you have looked at the pictures what else is there to say! The views on this fantastic new luxury 4 bedroom, 3.5 bathroom are simply out-of-this-world! Avalon truly has it all- luxury from the word go. Fine travertine marble, custom hard wood,... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 342177
    From
    $675
    / Night
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    1 / 61
    4 of 5 stars (1) Very good
    Holmes Beach
    8 Bedrooms / 6 Bathrooms / Sleeps 19
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • DVD Player
    • Patio
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Summer House 211 54th St Holmes Beach, Fl 34217 Summer House is a brand new 8 bedroom and 6 bathroom rental home just completed and rental ready! The rental home has so many fun options for everyone- close to the beach, Gulf and Bay water views, table games, water slide, spa, roof top deck with... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $315
    / Night
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    1 / 17
    5 of 5 stars (1) Excellent
    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Island Paradise #3 3708 Gulf Drive Unit 3 Holmes Beach, Fl. 34217 Island Paradise is just that- the best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. It simply does not get any... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $223
    / Night
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    1 / 20
    5 of 5 stars (2) Excellent
    Holmes Beach
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    Amenities & Details
    • Parking
    • Shared Outdoor Pool...
    • Internet Access
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Updated Holmes Beach Island home just steps to the Gulf of Mexico beaches. Enjoy this vacation rental with a caged heated pool and a brand new paver area with propane grill. This vacation rental has everything to offer with three bedrooms, brand new kitchen, nicely furnished and well equipped for... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $252
    / Night
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    1 / 16
    5 of 5 stars (1) Excellent
    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Gulf Place 2A 6700 Gulf Drive #2 Holmes Beach, Fl 34217 Direct Gulf front newly remodeled 3 bedroom, 2 bath condo with large open covered balcony. Breathtaking views of the Gulf of Mexico right out your window . Bright and light and very inviting and features a large open balcony, updated... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    $126
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    5 of 5 stars (1) Excellent
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
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    • Pet-friendly
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    About this property
    The Terraces Condominium #6 3100 Gulf Drive Holmes Beach, Fl. 34217 The Terraces is an exquisite 2 bedroom 2 bath townhome located only steps from the Gulf of Mexico. Upscale Florida decor. All new furnishings and appliances. Lush tropical landscaping surrounding heated pool with adjoining... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    $157
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    4 of 5 stars (1) Very good
    Holmes Beach
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • DVD Player
    • Patio
    • TV
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    • Pet-friendly
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    • Child-friendly
    • x
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    About this property
    Beach Bliss 304 58th St. Unit A Holmes Beach, Fl. 34217 If you are looking for that perfect cozy island vacation getaway, than look no further! Centrally located to all that Anna Maria Island has to offer this 2 bedroom and 2 bathroom newly constructed private duplex has got it all! The tropical... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    $378
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    5 of 5 stars (1) Excellent
    Bradenton Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pet-friendly
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    About this property
    SandCastle # 8 (Maui Cove) 200 Gulf Dr. South Unit #8 Bradenton Beach, Fl. 34217 Maui Cove- the name says it all. This luxury 3 bedroom, 2 bathroom direct Gulf front condo brings a unique and fun Hawaiian style atmosphere. From the decorative surf boards displayed on the way, to the... View all property information
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    Bradenton Beach, Anna Maria Island 34217
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    $199
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    Anna Maria
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Deck
    • Internet Access
    • Dryer
    • Washer
    • Satellite TV
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    • Pet-friendly
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    • x
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    About this property
    Bring the family and come enjoy our beautiful beaches! This 4BR/4BA elevated home is only one short block to the beach with direct beach access. This spacious home has plenty of room for family with 2 king size beds, a queen bed and two twins. Large, fully equipped kitchen, laundry room with... View all property information
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    Anna Maria, Anna Maria Island 34216
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    $378
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    5 of 5 stars (1) Excellent
    Bradenton Beach
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Pet-friendly
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    About this property
    Coastal Cove 301 Church St. Bradenton Beach, Fl 34217 Coastal Cove is a brand new 5 bedroom + bonus room, 4.5 bathroom private rental home that has been newly constructed and is ready for rental! This luxury home offers sweeping Gulf and Bay water views from the rooftop deck, a private heated... View all property information
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
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    $378
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    4.5 of 5 stars (2) Very good
    Bradenton Beach
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Pet-friendly
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    About this property
    Coastal Winds 303 Church St. Bradenton Beach, Fl 34217 Coastal Winds is a brand new 5 bedroom + bonus room, 4.5 bathroom private rental home that is currently under construction with completion in early May 2014. Reservations excepted beginning June 1st, 2014. This luxury home offers sweeping... View all property information
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    Bradenton Beach, Anna Maria Island 34217
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    $263
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    4 of 5 stars (1) Very good
    Anna Maria
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Internet Access
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    • Pet-friendly
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    • Child-friendly
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    About this property
    Sunchase Villa 302 Gulf Blvd Anna Maria, Fl. 34216 Sunchase Villa is a true Old Florida, ground level beach cottage nestled on the north end of Anna Maria Island only a short walk to restaurants and shopping. There are fantastic Gulf Views from this well-appointed 4 bedroom, 4.5 bath private... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $182
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    4.5 of 5 stars (2) Very good
    Anna Maria
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
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    • Pet-friendly
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    • Child-friendly
    • x
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    About this property
    Whispering Winds 210 Sycamore Avenue Anna Maria, Fl 34216 Key West style 4 bedroom, 2 bath home just a short walk from the Gulf of Mexico. This home offers private heated pool, three covered decks overlooking pool, BBQ grill, two car garage, cathedral ceilings, tile, carpet, open floor plan... View all property information
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    Anna Maria, Anna Maria Island 34216
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    $94
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    4 of 5 stars (3) Very good
    Holmes Beach
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    • Parking
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
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    • x
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    About this property
    New features include wireles internet service, extended cable, digital phone with free nationwide long distance. If outside entertainment is what you desire then Runaway Bay is the answer. Runaway Bay has the largest heated pool on Anna Maria. Between the tennis courts, gym, pool, and sauna's... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    $145
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    5 of 5 stars (2) Excellent
    Anna Maria
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
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    About this property
    Southern Breeze #1 607 Fern Street #1 Anna Maria, Fl. 34216 ISLAND 6-PLEX - Newly renovated top to bottom June 2013! These are 2 bedroom, 1 bath ground level units located at the tip of Anna Maria Island just steps from the Bay. Heated pool with nicely landscaped surroundings. Each is... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $161
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    4 of 5 stars (2) Very good
    Anna Maria
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Washer
    • Dryer
    • Stereo System
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
    About this property
    The Light House welcomes you in with its tropical landscaping, canal view and calming green exterior. This nicely furnished two-bedroom, one-bath vacation rental on Anna Maria Island has everything you need to begin a relaxing and restful vacation. Newer appliances will make quick work of... View all property information
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    Anna Maria, Anna Maria Island 34216
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    $323
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    5 of 5 stars (6) Excellent
    Anna Maria
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Patio
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Washer
    • Dryer
    • Wi-Fi
    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    Steps from the white sand beaches of Anna Maria, this four-bedroom, three bath, elevated house is just the place to build sand castles and memories! Located on Pine Avenue in Anna Maria, this charming beach vacation rental with a new backyard pool is beckoning you to start your vacation now. A... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $198
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    5 of 5 stars (7) Excellent
    Anna Maria
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • DVD Player
    • Wi-Fi
    • Dryer
    • Stereo System
    • Satellite TV
    • Private Outdoor...
    • Washer
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Pineapple Cottage, centrally located on historic Pine Avenue in the city of Anna Maria, is the perfect place to slow down and catch your breath! This Anna Maria Island cottage is tastefully decorated with wood floors, granite and stainless kitchen, tiled shower and comfortable furnishings. The... View all property information
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    Anna Maria, Anna Maria Island 34216
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    $224
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    Holmes Beach
    3 Bedrooms / 7 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Internet Access
    • Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • x
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    About this property
    Welcome to Holly Jewel located at 727 Holly Road on the northern end of beautiful Anna Maria Island. This private and lovely three bedroom and 2 1/2 bath vacation rental features all that you will need to stay a week or a month! Feel the breezes through the lanai or lounge in the private yard... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $233
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    5 of 5 stars (7) Excellent
    Anna Maria
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Satellite TV
    • Dryer
    • Stereo System
    • Washer
    • Fireplace
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This two-bedroom, two-bath vacation rental is located on the quiet north end of Anna Maria Island. Whispering Pines is just three houses from one of the most beautiful beach accesses on the island. This classic 1920's beach cottage has been lovingly restored. The original wood molding, fireplace,... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $215
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    1 / 24
    5 of 5 stars (4) Excellent
    Anna Maria
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Private Outdoor...
    • Washer
    • Deck
    • Satellite TV
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Come and enjoy your own private Island Oasis! Located on the north end of Anna Maria Island in the city of Anna Maria, one block from the bay and a few blocks from the City Pier, this charming vacation rental will allow for some serious relaxation. This home-away-from-home offers two bedrooms and... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $152
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    4.5 of 5 stars (5) Very good
    Anna Maria
    1 Bedroom / 1 Bathroom / Sleeps 4
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    Amenities & Details
    • Stereo System
    • Grill
    • Satellite TV
    • Dryer
    • Wi-Fi
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    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
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $215
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    4.5 of 5 stars (8) Very good
    Anna Maria
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Amenities & Details
    • Grill
    • Washer
    • Private Outdoor...
    • Patio
    • Wi-Fi
    • Dryer
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Location, location, location. Welcome to the quaint and quiet north end of Anna Maria Island! This classic AMI elevated, open floor plan vacation rental boasts three bedrooms and two baths with plenty of room for a large family or group to spread out and relax! Two queen-size beds, a full-size... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $194
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    5 of 5 stars (1) Excellent
    Holmes Beach
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Parking
    • Dishwasher
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ALL new ground level duplex with private heated pool and short stroll to the beach. This vacation rental has everything to offer with three bedrooms two bathrooms, TV's in each room and all the comforts of home. Please note, this property requires a Friday to Friday stay. In some cases... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217