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$90

2 BR / 1 BA / Sleeps 6

Anna Maria Island--Two Month Min.--Gorgeous! - Anna Maria Island vacation rentals
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$90

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Anna Maria Island--Two Month Min.--Gorgeous!

2 BR / 1 BA / Sleeps 6 | Quick view

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This newly decorated and refurbished condo is the answer to your dreams this fall. This 2 bedroom 1.5 bath condo is 300 steps to the beautiful white sands and crystal blue waters of Anna Maria Island. The condo is completely turn-key ready--nothing to bring but your swimsuit and toothbrush. Condo has 2 large bedrooms…
  • Suitable for children
  • Suitable for the elderly

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$105

1 BR / 1 BA / Sleeps 4

Four Beach Lovers 4 - Anna Maria Island vacation rentals
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$105

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Four Beach Lovers 4

1 BR / 1 BA / Sleeps 4 | Quick view

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Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnished. All four units feature a private patio area and a …
  • Waterfront
  • Internet Access
  • Grill
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$250

4 BR / 3 BA / Sleeps 10

Island Retreat - Anna Maria Island vacation rentals
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$250

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Island Retreat

4 BR / 3 BA / Sleeps 10 | Quick view

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Island Retreat 4805 2nd Avenue Holmes Beach, FL 34217 Key West meets Anna Maria Island in a dream vacation home. Island Retreat combines the best of both worlds, oozing a traditional south Florida style outside, with shaded balconies and intricate wooden architecture, with unrivalled, modern luxury on the inside. …
  • Heated Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$250

4 BR / 3 BA / Sleeps 10

Blue Heron - Anna Maria Island vacation rentals
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$250

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Blue Heron

4 BR / 3 BA / Sleeps 10 | Quick view

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Blue Heron 309B 65th St. Holmes Beach, Fl. 34217 A cute and fun island vacation retreat! It is newer construction with 4 bedroom, 3.5 bathroom and a private heated pool! It has everything you want in an tropical island vacation rental property- lush landscaping, flat screen HD TV's throughout, hardwood floors, …
  • Heated Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$150

3 BR / 3 BA / Sleeps 6

Seabreeze Cottage - Anna Maria Island vacation rentals
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$150

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Seabreeze Cottage

3 BR / 3 BA / Sleeps 6 | Quick view

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Seabreeze Cottage 5009 2nd Avenue Holmes Beach FL. 34217 This gorgeous property is nestled in a quiet residential neighborhood West of Gulf Dr, just over one block to the beach access. Seabreeze Cottage is just a one to two minute stroll to the beach. This pretty 3 bedroom/3 bathroom property is newly landscaped…
  • Heated Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$144

1 BR / 1 BA / Sleeps 4

26 Reviews

$144

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Alamanda Villas 5

1 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 26 Reviews

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Reviews

(26)

Alamanda Villas, located at 102 39th Street in Holmes Beach is a charming beachside complex featuring eight units surrounding a heated pool, tropical landscaping, multi-level decks and built in BBQ area. Anna Maria's white sandy beaches and the emerald green water of the Gulf of Mexico are just outside your door to …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(26)

RIGHT ON THE BEACH

Left on Feb 23, 2009 for a stay in October 2008

A great place for a couple to stay, in a wonderful part of the world. unfortunately the weakness of the British currency will defer most Uk citizens from returning in 2009.

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$300

5 BR / 4 BA / Sleeps 12

1 / 29

$300

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Harbor Breeze

5 BR / 4 BA / Sleeps 12 | Quick view

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Harbor Breeze 240 South Harbor Drive Holmes Beach, Fl. 34217 A spacious, newly constructed, home with 5 bedrooms and 4.5 bathrooms, Harbor Breeze will offer it all - deluxe private heated pool with hot tub - and the best part is that the pool overlooks the Bay with direct view of the Skyway Bridge! Harbor Breeze …
  • Heated Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$156

3 BR / 2 BA / Sleeps 6

1 Reviews

$156

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Pineapple Pointe

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Pineapple Pointe 117 51st Holmes Beach, Fl. 34217 How about this beautiful beach bungalow, nestled on a quiet street only a short 1-2 minute stroll to the white sand beach of the Gulf of Mexico. A perfect place to enjoy that family vacation and just get lost for a while. It features tasteful island decor …
  • Outdoor Pool
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Beautiful house just off the beach

Left on Feb 16, 2015 for a stay in February 2015

We just stayed here and loved it. It was just as described. Beach was easy to access. It was fairly cool when we were on the island so it was nice to sit by the pool out of the wind. We would stay again!

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$120

2 BR / 2 BA / Sleeps 6

16 Reviews

$120

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Seacrest II Condos 3

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 16 Reviews

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Reviews

(16)

Seacrest II Condo, Unit #3 at 3703 5th Avenue in Holmes Beach, is a very comfortably furnished and recently updated unit in a smaller complex, just a few short steps to the beach and located out of the way on a dead end street. Seacrest offers a heated pool, and every amenity to make your stay here a comfortable one. …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(16)

Needs some work

Left on Feb 25, 2009 for a stay in July 2008

This condo needed a lot of minor repairs. Every window treatment in the unit was broken. There was a bug infestation in the kitchen. Master bedroom mattress-very uncomforable(no mattress pad on mattress also) Light in pool kept falling out. No screens on lanai-other condos had them.

condo was for sale--not a desirable way to sell a property! Would not rent this condo again!

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$214

3 BR / 2 BA / Sleeps 6

1 / 23

$214

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Havana Cay

3 BR / 2 BA / Sleeps 6 | Quick view

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Havana Cay 109 Cedar St. Anna Maria, Fl. 34216 With this secluded and historic property, you will feel like you are vacationing at your own private 5-star resort. Havana Cay sits only 4 houses in from the beach and there are no busy streets to cross and zipping to and from the beach will be so easy! A quick 30 …
  • Private Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$285

3 BR / 2 BA / Sleeps 6

17 Reviews

$285

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Franks Beach House

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 17 Reviews

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Reviews

(17)

Franks Beach House is a beautiful three bedroom, two bath direct Gulf front home located at 3212 Gulf Drive in Holmes Beach. It features a very large open deck facing the beach as well as a screened lanai for when you want a little shade. The expansive beach stretches for miles in either direction.This spacious and …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Grill
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(17)

Spacious home with very good location

Left on Dec 30, 2010 for a stay in December 2010

Excellent location right on beautiful beach within walking distance of shopping center. The new deck is a great addition. Home is generously layed out, well equipped with dishes, cutlery, linens and blankets, as well as beach equipment. Home is older and has not been updated in recent years other than the deck. The couch is a back breaker.

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$329

4 BR / 3 BA / Sleeps 10

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$329

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Avalon

4 BR / 3 BA / Sleeps 10 | Quick view

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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, premium fixtures …
  • Private Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$200

2 BR / 6 BA / Sleeps 2

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$200

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BAY FRONT HOUSE WITH PRIVATE DOCK

2 BR / 6 BA / Sleeps 2 | Quick view

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Two Bedroom/2bath Home in Bradenton Beach Sleeps 6. This is a two bedroom/2bath home in Bradenton beach, with washer/dryer, new kitchen (granite counters), big screen/WiFi, great fishing on your own dock, on a quiet street, five minute walk to bridge street shopping area, two minute walk to the beach & …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Parking
  • Pet friendly

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$120

2 BR / 2 BA / Sleeps 4

1 Reviews

$120

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Sunbow Bay 109

2 BR / 2 BA / Sleeps 4 | Quick view
“ Poor ” 1 Reviews

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Reviews

(1)

Sunbow Bay Condominium #109 located at 3705 East Bay Drive in Holmes Beach has everything you could need or want for a memorable vacation. Conveniently close to shopping and restaurants yet out of the way and quiet. Sunbow Bay offers two heated pools, tennis courts, elevators, undercover parking and every conceivable …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Not what we expected

Left on Mar 09, 2015 for a stay in February 2015

Even though the location and views were great, we had problems. 2nd bedroom closet was locked and no one using it could hang cloths, my 90 year old mother-in-law needed some place to hang her cloths in her room. Frig. was full of partial used food, this turned our stomachs, and housekeepers had instructions not to throw it out prior to our arrival, all storage in the kitchen was used by owner…

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$200

2 BR / 2 BA / Sleeps 6

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$200

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A Sandbox by the Sea

2 BR / 2 BA / Sleeps 6 | Quick view

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A Sandbox by the Sea 507 Spring Avenue Anna Maria, FL 34216 A Sandbox by the Sea has a large luxurious tropical yard with a new private heated pool complete with tanning shelf and a bubbling spa tub!! Both water features have the option of digital light shows for evening fun! A press of a button allows you to …
  • Heated Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$137

2 BR / 2 BA / Sleeps 4

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$137

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Sun Plaza West 115

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Sun Plaza West #115 5608 Gulf Drive Unit 115 Holmes Beach, Fl. 34217 Sun Plaza West #115 is a beautifully decorated 2 bedroom and 2 bathroom condo, located directly on the Gulf! This gorgeous end corner unit, provides lots of privacy and stunning direct Gulf front views from both the living room and Master …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$83

2 BR / 2 BA / Sleeps 4

1 / 16

$83

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Shorewalk Condo, Newly Decorated w/lake view

2 BR / 2 BA / Sleeps 4 | Quick view

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The Shorewalk Complex is located along Cortez Avenue, the 'main-drag' in Bradenton. Sarasota Bradenton Airport is 15 miles from Shorewalk and Tampa International Airport is about 50 miles away. Ellenton Prime Outlet Mall is a 20 minute drive up I-75 N. Thrill seekers can enjoy Busch Gardens in Tampa and the world …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Wireless Internet
  • Washing Machine
  • Suitable for children

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$121

2 BR / 2 BA / Sleeps 4

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$121

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Sun-Day West: 2BR Family- & Pet-Friendly near Beach

2 BR / 2 BA / Sleeps 4 | Quick view

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Sun-Day West is the picture-perfect name for this two-bedroom, two-bath, elevated duplex. Located in Holmes Beach on Anna Maria Island, this vacation rental features a large, west-facing balcony that allows for plenty of sunshine in the afternoon and shade in the morning for that early cup of coffee before heading …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$288

5 BR / 3 BA / Sleeps 10

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$288

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Gulf Sound All Units

5 BR / 3 BA / Sleeps 10 | Quick view

Details

Gulf Sound is a gulf side, ground level tri-plex located at 2814 Gulf Drive in the southern end of Holmes Beach. This five bedroom, three bath property is fully equipped with everything you need for your stay. Each unit has been updated and is comfortably furnished. It's quiet, yet close to shopping, restaurants and …
  • Shared outdoor pool (unheated)
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$274

3 BR / 2 BA / Sleeps 6

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$274

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BEACHWALK

3 BR / 2 BA / Sleeps 6 | Quick view

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Three bedroom, two bath totally redone home with gorgeously landscaped backyard and heated pool! Only houses to the Gulf of Mexico and a beautiful white sand stretch of beach! This home has been updated with Mexican tile, granite countertops, and stainless kitchen! King-sized master bedroom, second queen-sized bedroom…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

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$171

3 BR / 2 BA / Sleeps 9

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$171

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Starfish

3 BR / 2 BA / Sleeps 9 | Quick view

Details

Starfish 105 79th Street Holmes Beach, Fl 34217 Location, location, location! This home is literally just steps to the beach- about a 30 second walk! It sits one house in, at the end of a dead-end, very quiet street. It just does not get much more convenient than this. It has 3 bedrooms and 2.5 baths, is bright…
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$200

3 BR / 2 BA / Sleeps 6

1 / 22

$200

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Villa Sand Dollar

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Villa Sand Dollar 113 75th Street Holmes Beach, Fl. 34217 Newly remodeled and a perfect location! This Island retreat offers 3 bedrooms, 2 1/2 baths and is a very short walk to the Gulf beach. The home sits West of Gulf Dr, only 5 houses in from the beach and about a 30 second walk! Offering views of the Gulf …
  • Outdoor Pool
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$214

4 BR / 3 BA / Sleeps 8

1 / 17

$214

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Sundown South

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Sundown South 300 N. Shore Unit A Anna Maria, Fl. 34216 This is a one of a kind brand new construction on Anna Maria Island. Sundown South has 4 bedrooms and 3 full baths and a private heated pool. Located on a beautiful lake on the prestigious North Shore Drive and only a very short walk to famous Pine Ave. It…
  • Private Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$190

2 BR / 2 BA / Sleeps 4

1 Reviews

$190

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Jukes Beach House

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Jukes Beach House is a charming, gulf front home located at 102 34th Street in Holmes Beach. This ground level home is conveniently located close to shopping and restaurants and on a pristine, wide expanse of beach. What could be better? This is a new and affordably priced gulf front home that will book quickly so …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Paradise

Left on Jul 07, 2014 for a stay in June 2014

Beautiful location, nice house, beach view nice. Interior layout very practical, large kitchen, family room and Cable TV perfect. Bedrooms spacious, bathrooms large

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$157

2 BR / 1 BA / Sleeps 6

3 Reviews

$157

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Escape to Serenity A: 2BR Pet-Friendly Pool Home

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Escape to Serenity sums it up for this quaint and cozy duplex (with no shared walls). You will feel as if you have landed on your own personal island with this gem of a property. This fantastic, two-bedroom, one-bathroom vacation rental will help you find some serenity. This home boasts an all-new kitchen, featuring …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children - over five
  • Suitable for the elderly

Details

Reviews

(3)

Everything we wanted!

Left on Jun 24, 2014 for a stay in June 2014

Great location, beautiful amentities and much appreciated attention to detail. Very clean and is a block from the beach!

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$157

3 BR / 2 BA / Sleeps 7

4 Reviews

$157

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Island Sun @ Anna Maria Island, FL

3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

END OF YEAR SPECIAL: Book your 2 week Island Sun Get Away and Save 5% off our advertised rates OR Save 10% on a 3 week stay from 9 Aug-20 Dec 2014. Contact us TODAY for your quote! (Offer not valid during Christmas/New Years Holidays.) Come to Island Sun @ Anna Maria and enjoy a luxurious, relaxing stay at one of …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(4)

We absolutely loved this island and this beautiful condo.

Left on Oct 13, 2013 for a stay in September 2013

So many nice places to visit. Island restaurants are excellent and the trolley is so convenient to travel the entire island. Also loved the beautiful walks on the beach in the morning and evening sunsets.
Condo is very comfortable with all necessities.
Loved shooting billiards with friends too.

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$120

2 BR / 2 BA / Sleeps 6

2 Reviews

$120

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While Away

2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

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 relax, unwind and …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Overall OK

Left on Aug 21, 2014 for a stay in July 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 washing machine was broken. We reported the problem to property management on Saturday and to their credit, they had someone out they same day; however, it wasn't fixed until the following Tuesday.

About a 5 minutes …

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$535

8 BR / 6 BA / Sleeps 20

1 / 40

$535

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Surf View

8 BR / 6 BA / Sleeps 20 | Quick view

Details

Surf View 209 54th St Holmes Beach, Fl 34217 Surf View is a newly constructed custom luxury home that is now ready for rental! The home is lavish and bold- it offers everything you would expect out of a luxury home and more!! Enjoy the private heated pool, waterslide, spa, swim-up Tiki table, rooftop deck with …
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $129

    1 BR / 1 BA / Sleeps 4

    1 / 19

    $129

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    Shell Haven

    1 BR / 1 BA / Sleeps 4 | Quick view

    Details

    Shell Haven 101 73rd St. Unit #4 Holmes Beach, Fl 34217 Direct Beachfront- steps to the beach! Shell Haven is a lovely 1 bedroom and 1 bathroom Gulf front condo that has been completely renovated top to bottom. This ground floor unit is just steps away from the pristine white sand beaches and features a west-facing…
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $100

    2 BR / 2 BA / Sleeps 4

    2 Reviews

    $100

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    SHOREWALK condo upstairs end IMG 3mins BEACH 10min

    2 BR / 2 BA / Sleeps 4 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    Highly desirable upstairs end unit with wonderful lake views... quiet yet a short walk to all the facilities that Shorewalk has to offer... two swimming pools with plenty of sun loungers ... two hot tubs... two tennis courts... table tennis and pool table at the clubhouse... Condo is fitted with up to date equipment…
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (2)

    Wonderful place!

    Left on Jan 05, 2015 for a stay in December 2014

    This condo is perfect for a family vacation (2 adults,3 kids under 10). It is very well equipped, incl umbrella, beach chairs, lunch bag and any possible kitchen utensil one might need. There was even a wonderful spice rack that came quite handy when cooking for a crowd. Condo is very clean and feels welcoming. Both rooms are large enough and decorated with taste. The complex is great, 2 pools…

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    $450

    5 BR / 4 BA / Sleeps 12

    1 / 9

    $450

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    Blue Sky Beach House

    5 BR / 4 BA / Sleeps 12 | Quick view

    Details

    Relax in this brand new luxury home just a block from the beautiful beaches of Anna Maria Island. The Blue Sky Beach House is one side of a newly constructed private duplex that will be complete mid-April. It is a stylish and cozy retreat with 5 bedrooms and 4 bathrooms, 5 flat screen TV's, private heated pool, …
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children

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    $129

    2 BR / 2 BA / Sleeps 4

    3 Reviews

    $129

    Inquire

    Sun Plaza West: 2BR Condo w/Tennis Courts near Beach

    2 BR / 2 BA / Sleeps 4 | Quick view
    “ Excellent ” 3 Reviews

    Details

    Reviews

    (3)

    Sun Plaza West, located in Holmes Beach on Anna Maria Island, is a fantastic get-away for the beach lover and tennis enthusiast! This two-bedroom, two-bath, end unit condo is located just steps to the white sand beaches of the Gulf of Mexico. This vacation rental features a large master suite with sliding glass doors…
    • Sauna
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Suitable for children - over five
    • Suitable for the elderly

    Details

    Reviews

    (3)

    Lovely stay at Sun Plaza West 101

    Left on Jul 12, 2014 for a stay in June 2014

    We stayed at Sun Plaza West for a week. The condo complex is very nicely maintained. The pool area is very nice with restrooms and lots of seating and umbrellas. The beach is a short walk and there are outdoor showers. We loved the storage room with chairs, umbrellas, beach toys and more. It was also a great place to store our ocean floats. We also liked the grocery carts for our use by the …

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    $171

    2 BR / 2 BA / Sleeps 4

    1 Reviews

    $171

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    Gulf View: 2BR Beachfront Condo with Amazing View

    2 BR / 2 BA / Sleeps 4 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    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 open living area …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Oh, what a view!

    Left on May 05, 2014 for a stay in April 2014

    Gulf View was clean, comfortable and "homey". We had a great week there this april! The view is, no question, outstanding ! The condo was clean and comfortable, the beds were fine, bathrooms terrific, kitchen fully stocked with everything we needed. Great place !

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    $283

    3 BR / 3 BA / Sleeps 8

    1 / 17

    $283

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    BLUE MARTINI

    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Newly built and beautiful is this professionally decorated 3 bedroom/3 bath home with private heated pool, swim-up tiki bar, and stone-scaped waterfall! Amazingly appointed with designer finishes throughout to the "Island-tune" of travertine, custom hardwood floors, wainscoted walls, vaulted ceilings, stainless steel …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children
    • Suitable for the elderly

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    $100

    2 BR / 2 BA / Sleeps 6

    7 Reviews

    $100

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    Fountainhead Condo 7

    2 BR / 2 BA / Sleeps 6 | Quick view
    “ Very Good ” 7 Reviews

    Details

    Reviews

    (7)

    Fountainhead Condo #7, located at 3400 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 itself offers every …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (7)

    Great! Just what we were looking for.

    Left on Feb 23, 2009 for a stay in March 2008

    This was a perfect place to stay. Had everything we needed. Nice and clean! Close to the beach and stores/restaurants.

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    $270

    4 BR / 4 BA / Sleeps 12

    13 Reviews

    $270

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    Pool Party Both sides

    4 BR / 4 BA / Sleeps 12 | Quick view
    “ Excellent ” 13 Reviews

    Details

    Reviews

    (13)

    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 outdoor bar with charcoal…
    • Shared outdoor pool (unheated)
    • Internet Access
    • Grill
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (13)

    Not as advertised

    Left on Feb 23, 2009 for a stay in July 2007

    This home was a big disappoint to us. The home was not well cleaned. We found blood stains on one of the comforters. Neither side of the home had been dusted in quite some time. The bathroom toilet had feces left on it. The pool was beautiful, EXCEPT it was dirty and looked like it hadn't been vacuumed in a long time. We lost a whole day of swimming til it was serviced by pool company. Also, …

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    $220

    2 BR / 2 BA / Sleeps 4

    1 / 18

    $220

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    Anna Maria island beach vacation apartment

    2 BR / 2 BA / Sleeps 4 | Quick view

    Details

    Overlooking the Gulf of Mexico Beach, on Anna Maria island 2 bedroom unit is arranged on two elevated levels for a total of 1,250 square feet. The apartment is beautifully decorated, fully furnished and has open view of the beach and is one of the Bird's Nest vacation apartments complex. The master suite has super …
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Suitable for children

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    $305

    3 BR / 3 BA / Sleeps 6

    1 / 25

    $305

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    Sandy Beach ~ RA38863

    3 BR / 3 BA / Sleeps 6 | Quick view

    Details

    Please note these Check-in Day Requirements for this property: Jun 24 - Jun 30 : Wednesday, Thursday, Friday, Saturday, Sunday, Monday and Tuesday check-out required.; Jul 26 - Aug 01 : Sunday, Monday, Tuesday, Wednesday, Thursday, Friday and Saturday check-out required.; Nov 22 - Nov 28 : Sunday, Monday, Tuesday, …
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Smoking allowed
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $241

    3 BR / 2 BA / Sleeps 8

    1 Reviews

    $241

    Inquire

    Island Paradise 3

    3 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    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 better than this. …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Beautiful Sunsets

    Left on Aug 17, 2014 for a stay in 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 were 200 yards from #1 rated hamburger joint in area and same to ice cream bar. Beach was not busy and very clean as well. Remember to bring your own beach chairs and umbrella. Would stay here again.

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    $514

    6 BR / 5 BA / Sleeps 14

    1 Reviews

    $514

    Inquire

    CASADELSOL

    6 BR / 5 BA / Sleeps 14 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    Welcome to the ultimate in Large Family luxury vacation Homes, with peeks of the Gulf of Mexico from the front balconies, and wide open intercoastal waterway views from the back of the home. This Brand New, 6 bedroom/5 bath home with Elevator features a large Tropical Heated Pool, Swim Up Table, and covered patio by …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Awesome Vacation

    Left on Aug 15, 2013 for a stay in June 2013

    We are a family of 10 and had a wonderful time at Casadelsol. Plenty of room for all. The kids spend most of the time in the pool, kayaking, fishing, or walking over to the ocean and playing there. So much to do that no one got bored. Loved it!

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    $150

    3 BR / 3 BA / Sleeps 8

    1 / 28

    $150

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    Calypso Cottage

    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Calypso Cottage 515 42nd St. Holmes Beach, Fl. 34217 Calypso Cottage is a stylish Mediterranean beach villa with all the finishing touches of what you would expect from an exquisite Anna Maria vacation home. Only a 5 minute stroll to the beach, the focal point has to be the brand new elaborate pool which wraps …
    • Heated Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $231

    3 BR / 2 BA / Sleeps 8

    1 / 25

    $231

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    BEACH RETREAT 206

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    3 Bedroom/2 Bath Villa, with its own Backyard, PRIVATE Heated pool, and only 75 yards to the beach! Beautiful new granite countertops, stainless appliances, and tile throughout. King Master bedroom with TV, Queen Bedroom w/ TV, Full/Twin bunk in the third bedroom with TV, and a full size Sleeper sofa in the living …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

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    $100

    2 BR / 2 BA / Sleeps 6

    7 Reviews

    $100

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    Seabreeze Condo B

    2 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 7 Reviews

    Details

    Reviews

    (7)

    Seabreeze Condo B, at 403 39th Street in Holmes Beach, is a very nicely furnished, well maintained, and comfortable two bedroom, two bath unit with a heated pool. This smaller complex is located just a few short steps to the beach and it's just a short stroll down a newly created path to, shopping and restaurants. …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Grill
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (7)

    Perfect location

    Left on Feb 23, 2009 for a stay in August 2008

    We rented this unit for our family and it was perfect. You can not beat the location. We could walk to stores and the beach. The pool was great, very private. Plenty of parking and a grassy area for the kids to play in. The unit is tastfully decorated and has almost everything you need. I would suggest to others.

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    $125

    1 BR / 1 BA / Sleeps 4

    1 / 11

    $125

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    Calm Horizon Efficiency near beach affordable

    1 BR / 1 BA / Sleeps 4 | Quick view

    Details

    Gorgeous Efficiency and steps to white sandy beaches from this 1 bedroom, 1 bath elevated vacation rental, one story up overlooking pool area. Stairs go up to small deck in front of the efficiency. With 3 x 8 open deck to enjoy the sunsets, or overlooking pool. Feel the warm gulf breezes lounging by the heated …
    • Internet Access
    • A/C or climate control
    • Deck
    • Parking
    • Grill
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

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    $115

    2 BR / 1 BA / Sleeps 6

    14 Reviews

    $115

    Inquire

    Sea Pirate 3

    2 BR / 1 BA / Sleeps 6 | Quick view
    “ Excellent ” 14 Reviews

    Details

    Reviews

    (14)

    Sea Pirate Condo #3, located at 3301 Gulf Drive in the heart of Holmes Beach is just a stone's throw from the tropic teal waters of the Gulf of Mexico. Situated in a much desired area, close to shopping and restaurants, this smaller complex features a large, screened and heated pool, on site coin operated laundry …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Grill
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (14)

    Fun on the beach

    Left on Jan 27, 2011 for a stay in January 2011

    The condo was very clean, nicely decorated, adequately furnished with everything we needed. Would love to stay there again sometime.

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    $121

    1 BR / 1 BA / Sleeps 4

    4 Reviews

    $121

    Inquire

    Island Place Cottage: 1BR Pet-Friendly Cottage

    1 BR / 1 BA / Sleeps 4 | Quick view
    “ Excellent ” 4 Reviews

    Details

    Reviews

    (4)

    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 cottage offers a fully…
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Parking
    • Pet friendly
    • Suitable for children - over five
    • Suitable for the elderly

    Details

    Reviews

    (4)

    Great cottage, great location.

    Left on Jul 26, 2013 for a stay in July 2013

    Cottage is perfectly located right in the heart of anna Maria. Quick walk to the Gulf beaches or to the Bay.

    Cottage was immaculate and perfect size for the three of us. A few years ago we stayed in the adjacent Pineapple House which was also perfect for our larger party during that visit.

    Would not hesitate to stay again.

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    $175

    3 BR / 2 BA / Sleeps 8

    1 / 16

    $175

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    Flamingo Cay, private boat dock, Palma Sola Bay

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    If you're seeking relaxation of recreation, this the rental home for you! Large solar heated pool in a screened-in lanai, dock facility featuring a floating dock, with a boat launch within 500 yards at Palma Sola Bay Beach. It is a short walk to the Bay Beach, and only 2.5 miles to the main beach on Anna Maria Island…
    • Waterfront
    • Ocean or water views
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $300

    6 BR / 6 BA / Sleeps 16

    1 / 27

    $300

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    Hemingway House

    6 BR / 6 BA / Sleeps 16 | Quick view

    Details

    Hemingway House 4103 4th Avenue Holmes Beach, Fl 34217 Hemingway House is a gorgeous, brand new elevated Island house that is tucked away on a quiet residential street and only a short one minute stroll to the Gulf beaches. This 6 bedroom and 6.5 bathroom luxury home is equipped with a private heated pool, spa, BBQ…
    • Outdoor Pool
    • Internet Access
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $171

    3 BR / 3 BA / Sleeps 8

    1 / 16

    $171

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    Sea Place

    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Sea Place 215 66th St. Holmes Beach, Fl. 34217 WOW- look at the reduced pricing on this one! This is a ground level island bungalow with 3 bedrooms and 2 full baths. Recently professionally re-decorated in a tasteful tropical island style, it also has a brand new heated pool to enjoy. One of the best values on …
    • Private Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $111

    3 BR / 2 BA / Sleeps 6

    2 Reviews

    $111

    Inquire

    North Beach Village 6323

    3 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    Palm Views is a comfortable and welcoming 3 bedroom, 2 bath townhome located in one of Anna Maria's finest neighborhoods just 1 block from the beach. Lush landscaping gives this home privacy and charm with a peek of the Gulf from the lanai. Townhouse-style layout features a garage on the ground level; screened lanai, …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Central heating
    • Suitable for children - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Met our expectations and our needs.

    Left on Jul 13, 2012 for a stay in June 2012

    I traveled to this property in June of 2012 with my partner, daughter, her friend and my parents. This condo worked out well for us. The Holmes beach area is beautiful & the people here are friendly. The realty company who handles this property was very friendly, helpful & professional. We had no problems working with them & they answered all of my many emails promptly.

    The master bedroom was …

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