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Holiday Homes and Apartments Holmes Beach, FL

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    All 535 Rentals in Holmes Beach
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    Travellers to Holmes Beach are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    $96
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    1 / 19
    4 of 5 stars (3) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (3) Make Enquiry
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    $142
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    1 / 16
    5 of 5 stars (2) Excellent
    3 Bedrooms / 7 Bathrooms / Sleeps 8
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    $1,475
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    5 of 5 stars (25) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    $1,251
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    1 / 22
    5 of 5 stars (8) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Grill
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    About this property
    Anna Cabana Bungalow #4 located at 3711 4th Avenue in Holmes Beach is in a ground level five unit complex that’s fun and affordable. It adjoins three other of the Cabana Bungalow units and is next door to the Cabana Beach House. With the numerous room configurations this is a perfect complex for... View all property information
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    $1,143
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    1 / 19
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Smoking allowed
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    • x
    About this property
    Lovely Bayside Condo recently remodeled, 2 Bedroom, 2 Bathroom, fully air conditioned, screened lanai, heated pool and covered parking. Easy access to: retail shops, grocery store and restaurants. 200 hundred yards to Free Island Trolley. Short walk to white sand beaches. Bike to nearby Robinson... View all property information
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    1 / 25
    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Satellite TV
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    • Wi-Fi
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    • Suitable for children
    • x
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    • x
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    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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    $214
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    1 / 12
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
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    About this property
    The 'Flip Flop' duplex is a fantastic recently remodelled duplex located one block from the white sandy beaches boasting professional landscaping, beautiful retro interiors, and its own private pool for each side of the duplex. Flop (the yellow side of the duplex) is a one bedroom, one bath duplex... View all property information
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    5 of 5 stars Reviewed 8 October 2014
    My husband and I loved Flop Cottage for many reasons. First of all, the landscaping is lush and tropical and the décor is fun and cozy - so you instantly feel like you are on...
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    $1,915
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    1 / 18
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    What a great place! The first time I came to Anna Maria Island, I thought how could I get a place like this! A place where a clean shirt and flip flops are the norm. Where people say hi and the food is great and affordable. I watched my first wedding at sunset while having dinner on the beach.... View all property information
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    5 of 5 stars Reviewed 19 April 2014
    I completely agree with the previous review. We loved the view and certainly appreciated being at a walking distance to the beach and to the stores. Also the kitchen is better...
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    1 / 14
    4 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
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    About this property
    Fountainhead Condo #5 is just a few steps from the beautiful beaches and azure blue water of the Gulf. This vacation rental is beautifully furnished and well equipped for your enjoyment. This two bedroom, two bath beach rental will sleep six with a queen size bed in one bedroom, two twin beds... View all property information
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    $218
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    1 / 12
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The 'Flip Flop' duplex is a fantastic recently remodeled duplex located one block from the white sandy beaches boasting professional landscaping, beautiful retro interiors, and its own private pool for each side of the duplex. Flip (the orange side of the duplex) is a one bedroom, one bath duplex... View all property information
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    5 of 5 stars Reviewed 31 May 2014
    Everyone I showed pictures of this home loved the retro look of it! The location is one block from the ocean in a very quiet neighborhood and everything you need is there. Ben...
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    $209
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    1 / 23
    4 of 5 stars (1) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    When you stay in this spacious two-bedroom family-friendly condo you will definitely become a beach potato! Just steps from Anna Maria Island's beautiful white sand beach in the city of Holmes Beach, with 1,349 square feet, this vacation rental provides plenty of space to relax and enjoy your time... View all property information
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    4 of 5 stars Reviewed 12 January 2015
    My husband and I traveled with our son and his fiancée. The condo is very clean, with several upgrades especially in the kitchen. Counters, appliances and provided dishes...
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    1 / 22
    5 of 5 stars (4) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Seaside Beach House #103 located at 102 68th Street in Holmes Beach is a direct Gulf front complex with a heated pool at beachside. It’s one of the nicest complexes on Anna Maria Island. This 'hidden away' property is located on a quiet side street in the northern end of Holmes Beach. The beach... View all property information
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    5 of 5 stars Reviewed 26 September 2014
    Seaside Beach House on Holmes Beach, Florida is a beautifully kept unit in a 10-unit complex right on the beach. Wonderful accommodations including washer and dryer in the unit...
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    $2,681
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    1 / 13
    4.5 of 5 stars (2) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    Spacious 3-level House with 2 large decks overlooking the beautiful Gulf of Mexico. House is fully furnished with a large flat screen TV and Bose Stereo System. Great Gulf views from living room and Master Bedroom. One Guest room also has a gulf view. Large garage is fully equipped with beach... View all property information
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    4 of 5 stars Reviewed 11 April 2015
    This house is lovely. It is well maintained and clean and has good sized rooms. The description is accurate. It is in an excellent location if you are looking for a beach week...
    5 of 5 stars Reviewed 23 January 2015
    A fantastic home, very well appointed, very clean and the perfect size for a group of 6. The location is spectacular, only steps from the beach and in the heart of Anna Maria...
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    $185
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    1 / 12
    4 of 5 stars (1) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Come relax and enjoy your beach vacation at The Cast Away! Located conveniently across from the Manatee Public Beach and the Gulf of Mexico. This two bedroom and one bath unit sleeps six with a queen size bed, two twin beds and a sofa bed. A full size kitchen and living room are included for your... View all property information
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    4 of 5 stars Reviewed 3 April 2015
    Mark was great to work with. He was very accommodating. As an extra bonus breakfast at the cafe was included which was delicious. We would stay there again.
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    $230
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    1 / 29
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Stay any week in the month of May 2015 for only $999.00 per week. Non-holiday and no other discounts would apply. Close to the Beach, classic, and cute!! Welcome to Little Miss Magic located at 116 81st Street on beautiful Anna Maria Island on the West Coast of Florida. Beach access is just 5... View all property information
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    $165
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    1 / 13
    4 of 5 stars (9) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Starfish Beach Cottage #4 is a totally renovated condo unit at 2913 Avenue E in Holmes Beach. This decorator furnished two bedrooms and two baths holiday condo is gorgeous and features high speed internet, upgraded furnishings and appliances. There is a private patio off the guest bedroom and a... View all property information
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    $218
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    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • 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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    $135
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    1 / 11
    4 of 5 stars (11) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Islands West Resort, located at 3605 Gulf Drive in Holmes Beach, is a tranquil resort with a large heated pool just a short stroll to the Gulf, shopping and restaurants. Enjoy the relaxing charm of island living when you stay at the Islands West Resort. The property consists of four, one bedroom... View all property information
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    5 of 5 stars Reviewed 9 May 2012
    After reading all of the good reviews and comments here and in the forums, we decided to contact the property management for this unit. We were pleased to receive a warm, personal...
    4 of 5 stars Reviewed 4 June 2014
    Die Unterkunft ist sicherlich ein paar Jahre alt, aber sieht neu renoviert aus. 1 Gemeinschaftspool, eigene Terrasse mit Tisch und Stühlen incl. Grill machen es einem schwer was...
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    4.5 of 5 stars (2) Very good
    2 Bedrooms / 7 Bathrooms / Sleeps 7
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • x
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    About this property
    Gracious Town Home located at 3701 Gulf Drive, Holmes Beach, Anna Maria Island, FL -- (2) Bed: (2.5) Bath: Accommodates up to (6) people: 1 Queen, 2 Twins & Sleeper Sofa: wirless internet, No smoking: No Pets. Absolutely fabulous two bedroom and two and a half baths in Gulfview Town Houses... View all property information
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    $166
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    1 / 10
    3.5 of 5 stars (3) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Brand New! BLUE LAGOON - Anna Maria Island's newest vacation rental villa is ready for your next vacation! Two bedroom, two bath with a huge Tropical pool and 10' waterfall right outside your back door. The pretty upgraded kitchen offer granite countertops, stainless appliances and ample... View all property information
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    1 / 13
    5 of 5 stars (2) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    A Seashell Throw From The The Pristine Gulf Of Mexico two bedroom, one bath, wireless internet holiday condo is a stone's throw away from the pristine Anna Maria Island beaches. This bright and sunny, ground-floor vacation rental condo features a relaxing beach decor, has an oversized heated pool... View all property information
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    5 of 5 stars Reviewed 23 May 2014
    Sea Pirate #2 is a great place to stay on AMI. The condo is very clean, well-appointed,comfortable, and nicely decorated and is so conveniently located across the street from an...
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    1 / 19
    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
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    • Wheelchair access
    • Elder access
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    About this property
    The Cove at Sandy Pointe #113, at 3601 East Bay Drive is a cheerful, two bedroom and two bath condo in a secluded complex close to shopping and conveniently located to the beach. Sandy Pointe features undercover parking and a large heated pool. Each unit has a large screened lanai.This well... View all property information
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    5 of 5 stars Reviewed 12 July 2014
    A perfect place to stay. The apartment was lovely. The pool was perfect. A walk across the street to the publix supermarket and a 2 minute trip to Holmes Beach. Everything we...
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    1 / 9
    4 of 5 stars (2) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • x
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    About this property
    Old Florida Style Cottage Duplex a Very Short Stroll to the Beach -- Holmes Beach, Anna Maria Island, FL -- (2) Bed: (1) Bath: Accommodates up to (4) people: 1 Queen & 2 Twins: No smoking: No Pets. Heated pool, shared. This newly remodeled and updated island duplex is just a stroll to the... View all property information
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    $161
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    1 / 23
    4.5 of 5 stars (3) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Professionally decorated with a comfortable island flavor, this new villa offers everything you'll desire for a truly memorable vacation! The location of this villa is centered directly in the middle of Anna Maria Island offering you an excellent location for your vacation stay. The villa... View all property information
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    3 of 5 stars Reviewed 31 July 2012
    The house is very well maintained and well equipped. The beds are comfortable and the decor is very nice. The pool is a good size, however, the enjoyment of the pool is marred...
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Grill
    • Internet Access
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Elder access
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    About this property
    Sirena del Mar is a three bedroom, two bath home located at 201 30th Street in Holmes Beach. This home has been totally renovated and features a small pool. Its two very short blocks to the wonderful, white sandy beaches.Sirena del Mar has a wonderful open design with all new kitchen cabinets and... View all property information
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    $306
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    1 / 18
    5 of 5 stars (2) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Beautiful, brand new, 3 bedroom/2.5 bath townhouse home with decorator furnishings throughout! Comfortable and roomy with great room, large open lanai, two car garage, and beautiful open kitchen area with granite countertops. Great central location a couple of blocks to the beach, and easily... View all property information
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    1 / 11
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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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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    5 of 5 stars Reviewed 2 May 2015
    First off I would like to thank Anna Maria rentals for their excellent and no hassle service. They sent me a key code, and I never had to go their office to do anything. We came...
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    1 / 11
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • x
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    About this property
    Star Fish Beach 3 - Anna Maria Island's premier upscale development offers this vacation rental condo for the discriminating vacationer only. Every detail has been taken care of with our guest's relaxation in mind. A heated pool in a tropical landscape offers an oasis to relax after a long day of... View all property information
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    5 of 5 stars Reviewed 2 July 2014
    We stayed at the Starfish Beach 3 in June of 2014. This was a last minute booking (reserved a few hours before arriving) so we were very excited to get such a nice rental unit...
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    1 / 17
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • x
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    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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    5 of 5 stars Reviewed 18 August 2014
    The unit was very clean & well kept as well as the entire building. Our view of the Gulf of Mexico from the living room was breath taking. The pool was nice size and clean. We...
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    1 / 25
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Gym
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Enjoy one of the most breathtaking views on the island from this lovely two bedroom/two bath upstairs unit at West Bay Point Moorings. Not only are the views spectacular, but the entire complex is unique on Anna Maria, with large, open vistas, lush landscaping, four heated swimming pools, two... View all property information
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    4 of 5 stars (8) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    About this property
    Endless Sunset Views From your private screened balcony overlooking the white sandy beach of Anna Maria Island. Spacious three bedroom, two bath 2nd floor direct Gulf front condo nestled in the soft white sand beaches next to the sparkling Gulf of Mexico waters. This vacation rental... View all property information
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    1 of 5 stars Reviewed 4 May 2015
    we had visitors from the West Coast of the US come all the way across the country to visit Anna Maria Island. After a day, the BITING FLEAS inside the condo from a dirty dog or...
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    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    The Bman Beach Cottage located at 2812 Avenue B in Holmes Beach is a cute 2 bedroom 2 bath private home. This ground level home has two screened lanais one overlooking the pool and Jacuzzi. The kitchen has been newly updated as well as one of the bathrooms. This property has long distance and WiFi... View all property information
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    5 of 5 stars Reviewed 7 November 2014
    I stayed at the cottage for a little over two months. The owner has stocked the home with everything you could possibly want or need - comfortable, easy to care for, and the pool...
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    4.5 of 5 stars (7) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
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    • Suitable for children
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    About this property
    The Cove at Sandy Pointe #205, at 3601 East Bay Drive is a cheerful, two bedroom and two bath condo in a secluded complex close to shopping and conveniently located to the beach. Sandy Pointe features undercover parking and a large heated pool.This well appointed and recently refurnished unit... View all property information
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    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Pets allowed
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    About this property
    Fountainhead Condo #4, located at 3402 6th Avenue in Holmes Beach is just a few steps from the beautiful beaches and emerald green water of the Gulf. This eight unit complex has a heated pool and laundry room on site.This unit is beautifully furnished and well equipped for your enjoyment. The unit... View all property information
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    2.5 of 5 stars (4) Poor
    2 Bedrooms / 6 Bathrooms / Sleeps 6
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    About this property
    Panoramic views from this wonderful vacation rental duplex which sits literally foot steps to the Anna Maria Island sugar white sands. Views are visible from the large open deck, the front dining area and kitchen. There are two large bedrooms both offering king size beds decorated in a... View all property information
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    1 of 5 stars Reviewed 11 November 2014
    filthy from top to bottom--the prior reviewer was being very generous--it is not just superficially clean, it is down right filthy--never mind that it is a rehab done as cheaply...
    2 of 5 stars Reviewed 11 March 2014
    Delightful location on the beach, ruined by poor general upkeep of the building (1940s house converted into TWO units)and general lack of attention to detail in kitchen and...
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    4.5 of 5 stars (9) Very good
    3 Bedrooms / 8 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Shared Outdoor Pool...
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    • Pets allowed
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    • Suitable for children
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    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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    5 of 5 stars (3) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Pets allowed
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    • Suitable for children
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    About this property
    Ground level duplex directly on the white sandy beach at Holmes Beach on Anna Maria Island - what a find! This pretty beach cottage is newer throughout. The living room is cozy but well equipped with a flat screen TV and comfortable furnishings. The brand new kitchen offers all new... View all property information
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    4.5 of 5 stars (8) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Grill
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    • Shared Outdoor Pool...
    • Water Views
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    • Pets allowed
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    • Suitable for children
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    About this property
    Anna Maria Beach Place #2, located at 201 35th Street in Holmes Beach is a charming beachside complex featuring six units surrounding a heated pool and tropical gardens. Immediately across a rarely traveled, dead end road are the white sandy beaches and the emerald green water of the Gulf of... View all property information
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    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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    3.5 of 5 stars (2) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    About this property
    The While Away, located at 6203 Holmes Blvd. in Holmes Beach is a two bedroom, two bath, ground level duplex with a private heated pool. This very spacious duplex is located in a quiet, residential neighborhood just a short stroll to the beach, shopping or the library. It’s a perfect spot to... View all property information
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    3 of 5 stars Reviewed 22 August 2014
    The property was clean and we'll kept. The AC had trouble maintaining a constant, comfortable temp during the day. We arrived on Thursday and discovered on Friday night that the...
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    4.5 of 5 stars (6) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Dishwasher
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    • Pets allowed
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    About this property
    Tiffany Place located at 7000 Gulf Drive Holmes Beach, FL is a gulf front condominium complex on the Gulf of Mexico. Sit and relax on your private balcony of your vacation rental or take a dip in the large heated pool. This well cared for Gulf Front condo is nicely furnished and one that you will... View all property information
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    5 of 5 stars (11) Excellent
    2 Bedrooms / 6 Bathrooms / Sleeps 5
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    • Pets allowed
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    About this property
    Updated Island Home just steps to the Gulf Beaches with heated pool with waterfall...this multi level vacation rental has everything to offer with two bedrooms, updated kitchen, brand new furnishings and fun sun room off the pool area. The chic beach decor is tasteful, fun and perfect for the... View all property information
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    5 of 5 stars Reviewed 10 July 2014
    Your own private pool four houses from the beach. Beachside, so no crossing of busy streets, lovely private couple of steps that open up to your own beach paradise. The house is...
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 7 Bathrooms / Sleeps 6
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    • Pets allowed
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    About this property
    Recently remodeled three bedroom two and a half bath townhome located at 6250 Holmes Blvd in desirable North Beach Village of Holmes Beach with a two car garage. New stainless steel appliances in the custom kitchen and a washer/dryer at your fingertips. The large community heated swimming pool is... View all property information
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    5 of 5 stars (8) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    About this property
    3205 Gulf Drive at Palm Isle Village in Holmes Beach, FL - Anna Maria Island's NEWEST and finest condominium complex offers several fabulous holiday villas all designer decorated and with floor plans maximizing water views. A heated pool is a great place to relax after a day at the beach. Widow... View all property information
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    4 of 5 stars (6) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Internet Access
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
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    • Pets allowed
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    About this property
    The Cove at Sandy Pointe 111, located at 3601 East Bay Drive in Holmes Beach is an exceptional three bedroom, three bath bay front unit. Located directly on the bay in a quiet location, this unit overlooks a natural mangrove preserve. The complex features a large heated pool.This spacious unit... View all property information
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    4 of 5 stars (13) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Pets allowed
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    About this property
    Magnificent elevated Mediterranean style vacation rental three bedroom and three bath villa in a perfect Holmes Beach location close to the pristine beaches, choice restaurants and fabulous shopping experiences. Private home has a lushly landscaped yard and lots of character! Maple hardwood... View all property information
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    5 of 5 stars Reviewed 15 May 2012
    My husband, toddler, and I just came back from a week-long stay at this beautiful home. It was more than enough room for us and we can see even bringing the grandparents next...
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    4 of 5 stars (13) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Internet Access
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
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    About this property
    Seaside Beach House is a two-story ten-unit condominium located at 102 68th Street in Holmes Beach on Anna Maria Island. It is a Gulf front complex with a heated pool at beachside. Unit 205, with its own private staircase, adds special privacy and is quietly sequestered at the north end of the... View all property information
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    1 of 5 stars Reviewed 4 October 2014
    this is an old condo..paper thin walls...public access beach...kitchen had no useful pots or pans....bathroom was a nightmare...holmes beach is an ashtray and looked like a camp...
    5 of 5 stars Reviewed 15 August 2011
    This condo is a really good value for the price. Great quiet location in Holmes Beach and spectacular beach!! We took our bikes and went riding every night. Very safe area to...
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    4 of 5 stars (13) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 12
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    About this property
    The Pool Party, located at 6102 Marina Drive in Holmes Beach, is a beautiful duplex featuring two bedrooms and two baths on each side with a pool area that is unsurpassed! This property features a heated pool with a spa surrounded by mature, native plantings as well as a shaded hammock and an... View all property information
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    4 of 5 stars (8) Very good
    1 Bedroom / 1 Bathroom / Sleeps 3
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    About this property
    ** VACATION YOUR WAY - this property offers flexible ARRIVAL AND DEPARTURE dates ** Brand NEW Rates for 2012. Check out our standard rates which are low, low, low. Fantastic Island triplex located at 104 B 29th Street, Holmes Beach, Anna Maria Island, FL -- (1) Bed: (1) Bath: Accommodates up... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dryer
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    • Private Outdoor...
    • Washer
    • Waterfront
    • Wi-Fi
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    • Pets allowed
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    About this property
    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 better than this. It is like you are sitting on the deck of a cruise... View all property information
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    Holmes Beach Vacation Rentals

    Holmes Beach is a small town on Anna Maria Island in the Gulf of Mexico just south of Tampa Bay. It boasts miles of gorgeous white, sandy beaches, emerald Gulf waters, abundant sunshine, and an eclectic selection of vacation rentals. Visitors to Holmes Beach can stay anywhere from a luxurious beachfront house to a rustic rental cottage. Friendly locals welcome everyone to relax and enjoy this “Florida old charm” paradise.

    Where to Stay in Holmes Beach

    Rental homes can provide not only flexibility but the amenities of the best resorts at a fraction of the price. If you are vacationing with the family, having extra space to spread out is also an asset. Whether you want a weekend getaway or a long trip the rental choices are endless, and you’re sure to find something that will fit your family’s needs.

    Fun things to do in Holmes Beach

    A scooter is an inexpensive and fun way of getting around the island from your vacation rental. If you want to spend a day on the water, there is excellent fishing in the waters surrounding Anna Maria Island. Take a charter boat and head out in the Gulf for an exciting day of sport fishing. The grouper, snapper, or mackerel you catch can provide the ingredients for a delicious seafood dinner at your vacation rental. Inshore or backwater fishing is also very popular.

    Enjoy a beach picnic with the locals under the Australian Pines, or find a secluded cove and enjoy some private sunbathing. Prefer an animated beach crowd? Then the all-you-can-eat pancake breakfasts at "Cafe on the Beach" is your scene.

    More beach Fun

    Join a volley ball game. There are numerous nets along the beach, and there is always an exciting game taking place. Not in for that much activity? Then lie on the beach soak up some sun while you cheer for your favorite team.

    Dining and entertainment

    Enjoy a burger and a cold beer at Dusty’s Tavern steps away from your vacation rental. The Beach House Restaurant provides beachfront dining and live music for your enjoyment. Enjoy fresh grouper and a beer close to your vacation rental. You can also rest and relax at the pool at your vacation rental and enjoy a barbeque with your family and friends. Whatever your choice, you will leave the island with unforgettable memories.