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$266

4 BR / 3 BA / Sleeps 11

SS Salamander Both units - Holmes Beach vacation rentals
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$266

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SS Salamander Both units

4 BR / 3 BA / Sleeps 11 | Quick view

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Welcome to the SS Salamander located at 121 50th Street in Holmes Beach. This recently updated duplex is just a one block stroll down a side street to the beautiful white, sandy beaches. It’s located in a quiet and preferred residential neighborhood yet it's easily within walking distance to restaurants and shopping…
  • 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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$229

3 BR / 3 BA / Sleeps 6

5 Reviews

$229

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A Pearl of a Beach Home with private Pool & Spa

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

*** LARGE HEATED FREE-FORM, LUXURY POOL AND SPA WITH SPACIOUS PAVED SURROUND - AVAILABLE FROM AUGUST 2014 - TOGETHER WITH TROPICAL LANDSCAPING, AUTOMATED GARDEN LIGHTING AND LARGE GROUND FLOOR LANAI. *** Leave your troubles behind as you cross to Anna Maria and surrender to the island pace. Our beach house (a …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(5)

Best vacation in 40 years!

Left on Mar 05, 2014 for a stay in February 2014

The owners, Mike and Lesley Crowther were wonderful to deal with

before, during and after our two week stay at their home. The house

was immaculate and had everything we could have needed during our

stay. Large bedrooms and baths with excellent beds and showers. The

kitchen and laundry room appliances were all in new condition. We

found ourselves wanting to eat in most of the time as the …

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$125

2 BR / 2 BA / Sleeps 6

1 Reviews

$125

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Beach Bliss

2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Beach Bliss 304 58th St. Unit A Holmes Beach, Fl. 34217 If you are looking for that perfect cozy island vacation getaway, than look no further! Centrally located to all that Anna Maria Island has to offer this 2 bedroom and 2 bathroom newly constructed private duplex has got it all! The tropical landscaped, private…
  • Private Pool
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Enjoyed the pool!

Left on Aug 02, 2014 for a stay in July 2014

Stayed a week at Beach Bliss. Nice home with beautiful décor. The swimming pool was very inviting...not very big but enough for floating and entertaining. The house was very clean and the kitchen was equipped with the basics. The beds were comfortable and the rooms were of good size. Plenty of towels, bath and beach, so that was a plus. All in all the home had a very tropical theme and had…

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$124

2 BR / 2 BA / Sleeps 4

Coast House - Holmes Beach vacation rentals
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$124

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Coast House

2 BR / 2 BA / Sleeps 4 | Quick view

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Coast House 107 75th Street Holmes Beach, Fl. 34217 This property is right next to the beach! This exquisite 2 bedroom and 2 bathroom condo home is just 200 ft to the Gulf of Mexico. This property exudes high end quality throughout, with beautifully decorated yet cozy furnishings. Right off of the living room you …
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$236

3 BR / 2 BA / Sleeps 8

CHIKI TIKI EAST - Holmes Beach vacation rentals
1 / 26

$236

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CHIKI TIKI EAST

3 BR / 2 BA / Sleeps 8 | Quick view

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Brand New remodeled cottage with a beautifully landscaped private backyard, Heated pool with Swim-up Tiki, Tiki Bar with Fan , paver deck, and Full kitchen with Granite countertops and Stainless Steel appliances. Bamboo Ceilings and Tiki Feel throughout. Sleeps up to 8 people, 1316 Sq. ft. 303B 64th St., Holmes …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$100

2 BR / 2 BA / Sleeps 4

The Terraces 6 - Holmes Beach vacation rentals
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$100

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The Terraces 6

2 BR / 2 BA / Sleeps 4 | Quick view

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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 Pergola for added …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$215

3 BR / 2 BA / Sleeps 8

1 Reviews

$215

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Island Paradise 2

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

Details

Reviews

(1)

Island Paradise Unit # 2 3708 Gulf Dr. Unit # 2 Holmes Beach, Fl. 34217 This beautiful Gulf front condo makes you feel like you are living right on top of the beautiful blue waters of the Gulf of Mexico. The entire living area and kitchen are facing west with lots of crystal blue water in front and the master …
  • Shared outdoor pool (unheated)
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

I would go back Tomorrow if I could

Left on Oct 14, 2014 for a stay in October 2014

Finally a villa that looks exactly like the pictures. It was very clean, felt new, good views and on the beach. We were very lucky in that we had we were the only ones in the 6 apartment condo so the place was very quite. Bedroom 1 was very nice with a large bed and tv although the shower could have been better, room 2 had 2 beds and a tv, room 3 was a queen but strangely didn't have a tv (this …

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$285

3 BR / 2 BA / Sleeps 8

18 Reviews

$285

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Tiki

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 18 Reviews

Details

Reviews

(18)

The Tiki, located at 3214 Gulf Drive in Holmes Beach is a spectacular three bedroom, two bath home directly on the emerald waters of the Gulf of Mexico. While the Tiki is located in a very quiet area on a secluded beach area, it is within a five minute walk to shopping and restaurants. Recent renovations include …
  • 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

(18)

Spring Break 2009

Left on Apr 08, 2009 for a stay in March 2009

The house was great! Very clean, everything you would need was supplied with the exception of beach chairs. The location was very easy to get to. The beach beautiful. We arrived early and were given keys to the house as soon as it was released from the cleaning crew.

Our only complaint was a short note stating the water heater was to be replaced on Monday, in our check in package. First guy …

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$150

3 BR / 2 BA / Sleeps 8

1 / 16

$150

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Caribbean Surf

3 BR / 2 BA / Sleeps 8 | Quick view

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Caribbean Surf 306 67th Street Unit B Holmes Beach, Fl 34217 Caribbean Surf is one side of a newly constructed private duplex that offers a discreet backyard with a tropical pool, swim-up Tiki table and BBQ grill. This brand new Island home is equipped with 3 bedrooms and 2 bathrooms and is centrally located on the…
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $171

    3 BR / 2 BA / Sleeps 9

    1 / 18

    $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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    $264

    4 BR / 3 BA / Sleeps 8

    4 Reviews

    $264

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    Twin Heron: 4BR Family-Friendly Pool Home

    4 BR / 3 BA / Sleeps 8 | Quick view
    “ Excellent ” 4 Reviews

    Details

    Reviews

    (4)

    This beautifully furnished four-bedroom, 3.5-bath Anna Maria Island vacation rental is just over a block to the beach! With a large great room layout and balconies in front and rear of the house there is plenty of room for vacationing in this awesome home. On the main floor you will find the main bedroom that has a …
    • Spa/Whirlpool
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Suitable for children - over five
    • Suitable for the elderly - ask

    Details

    Reviews

    (4)

    Twin Heron on Anna Maria Island is very relaxing.

    Left on Aug 25, 2014 for a stay in August 2014

    We enjoyed our stay at Twin Heron on Anna Maria Island. This is a very nice, spacious and clean rental property that has all the upscale comforts of home. Scenic grounds well maintained. Short walk to the beach and even an island trolley is available. Recommend dining on the porch of the "Waterfront Restaurant" with great views of Tampa Bay. Coastal Cottages AMI is a professional vacation rental …

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    $125

    3 BR / 2 BA / Sleeps 6

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    $125

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    Villa Paradise

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Villa Paradise 5608 Holmes Blvd Holmes Beach, Fl. 34217 Villa Paradise is a brand new 3 bedroom, 2 bath ground level home that is only a short 2-3 minute walk to the Gulf beaches. This property has lush tropical landscaping and is surrounded by a privacy fence and also includes a PRIVATE heated pool as well. …
    • Outdoor Pool
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

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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

    Details

    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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    $125

    1 BR / 1 BA / Sleeps 4

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    $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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    $120

    2 BR / 2 BA / Sleeps 6

    16 Reviews

    $120

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    Seacrest II Condos 1

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

    Details

    Reviews

    (16)

    Located in the heart of Anna Maria Island, at 3703 5th Avenue, in the sun-drenched community of Holmes Beach this roomy two bedroom, two bathroom condo is a recently up-dated, re-decorated and well maintained roomy, light and airy unit with covered parking plus a heated pool. Leave the car at home because this small …
    • 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)

    Great Island Getaway!!

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

    We had a WONDERFUL stay in this condo! My family came down for my daughter's graduation; it was a perfect place - close to Bradenton, but with the island feel. It was great being so close to the beach, and the pool was nice and private. The condo was lovely - all the necessities, lots of extras, and everything was top-notch. The beds were very comfortable, and we spent lots of time on the …

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    $189

    2 BR / 2 BA / Sleeps 6

    3 Reviews

    $189

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    SUN DAZE

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

    Details

    Reviews

    (3)

    Adorable and Updated 2 BR/2BA villa with a private heated pool. This villa is located on a quiet residential street, just a short walk to the beautiful beach, with no busy streets to cross to get there, and easily walkable to the 'downtown' Holmes Beach area for shopping and restaurants and more! Features include …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (3)

    Would totally stay here again!

    Left on Jul 24, 2014 for a stay in July 2014

    This home was nicely furnished, clean, and in a great location. It was a short walk (4-5 minutes pulling a wagon and walking with kids) to the beach. We had no busy streets to cross- just down a block and a half. The street was quiet. The pool was beautiful as were the upgrades in the home. We could sometimes hear the sound of the television from the other unit (126A) through the walls, but we …

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    $421

    6 BR / 5 BA / Sleeps 16

    1 / 29

    $421

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    Gulfside Oasis

    6 BR / 5 BA / Sleeps 16 | Quick view

    Details

    Gulfside Oasis 204 66th St. Holmes Beach, Fl. 34217 This is it- the pinnacle of Anna Maria Island luxury! Gulfside Oasis is a brand new luxury home that combines comfort, class and convenience. Spacious, with 6 bedrooms and 5 full bathrooms, this property is the perfect get-away for larger parties or multiple …
    • Private Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $122

    2 BR / 4 BA / Sleeps 4

    1 / 12

    $122

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    Anchors West, 125 steps to the beach and sunsets

    2 BR / 4 BA / Sleeps 4 | Quick view

    Details

    Anna Maria Island, West of Bradenton Florida. A quiet townhouse steps to the Gulf of Mexico. A bird and Turtle sanctuary. Beautiful beaches with dining and shopping nearby. This is the most beautiful island just North of Longboat Key Florida. The sunsets are the most beautiful. Enjoyable for everyone. Swimming in …
    • Wireless Internet
    • A/C or climate control
    • Central heating
    • Parking
    • Grill

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    $125

    3 BR / 2 BA / Sleeps 8

    1 / 13

    $125

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    Tropic Dream

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    Tropic Dream 5606 Holmes Blvd Holmes Beach, Fl. 34217 This is a newly renovated, ground level 3 bedroom, 2 bathroom home is only a short 2-3 minute walk to the beach. Surrounded by lush tropical landscaping, the home has a private heated pool and plenty of sunshine! It is the South unit of the duplex. There is…
    • Heated Pool
    • High Speed Internet
    • Patio
    • Television
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $171

    3 BR / 2 BA / Sleeps 6

    1 / 15

    $171

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    Sea Breeze Pool Home

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Sea Breeze is a private home with 3 bedrooms and 2 bathrooms and a brand new heated pool! The home is comfortable and well stocked. Wood floors throughout, open floor plan and cathedral ceilings with large sliders that open onto a large screened porch. Close proximity to the beach, about 3 blocks. Located in …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Central heating
    • Suitable for children
    • 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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    $265

    2 BR / 2 BA / Sleeps 6

    16 Reviews

    $265

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    Gulf Front - Shady Pines

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

    Details

    Reviews

    (16)

    SPECIAL - Nov. 07 -21, 2014 $200.00 / night + tax & cleaning (4 night minimum) Completely remodeled, 2 BR, 1-1/2 bath beach house right on the beautiful Gulf of Mexico. Walk out the door to a wide, white, powdery beach and the Gulf. This 2 bedroom beach house is located in the most perfect spot you willl …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

    Details

    Reviews

    (16)

    Rita Stewart

    Left on Nov 13, 2010 for a stay in November 2010

    We recently spent 5 glorious days at Shady Pines, where our biggest decision was where to watch the sunset-from the family room where the whole beach side is glass, the adirondack chairs in the back yard at the edge of the sand, or 20 steps further at the edge of the water. This allows the sun to set right in front of the viewer. This house is absolutely wonderful-sooo clean, original art, and…

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    $125

    3 BR / 2 BA / Sleeps 8

    1 / 12

    $125

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    Egrets Landing

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    Egrets Landing 303 74th St. Unit A Holmes Beach, Fl. 34217 Egrets Landing is a brand new ground level construction with a private heated pool! Offering the best of all that Anna Maria Island has to offer with its central location, you are never too far from white sandy beaches, local cuisine, shops and the popular …
    • Heated Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $350

    5 BR / 4 BA / Sleeps 14

    1 / 26

    $350

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    Sunset Landing

    5 BR / 4 BA / Sleeps 14 | Quick view

    Details

    Sunset Landing 4804 Gulf Dr. Holmes Beach, Fl. 34217 Sunset Landing is a brand new 5 bedroom+ bonus room, 4.5 bathroom vacation home sitting West of Gulf Dr. and an easy 2 minute walk to the beach. Professionally decorated, this fabulous vacation home has it all! Granite counters, travertine tile, fine fixtures…
    • Private Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $143

    2 BR / 2 BA / Sleeps 6

    4 Reviews

    $143

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    Gulf Sands: 2BR Flip-Flop Ready Beachfront Condo

    2 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 4 Reviews

    Details

    Reviews

    (4)

    Grab your flip flops and get ready to head to the beach when staying in this Gulf Sands condo! With a private balcony overlooking the turquoise waters of the Gulf of Mexico, this vacation rental is a fantastic place to stay during your Anna Maria Island vacation. There is plenty of space for family and friends in …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for children - over five
    • Suitable for the elderly

    Details

    Reviews

    (4)

    Great value for the price.

    Left on Jul 24, 2013 for a stay in May 2013

    We stayed here in May 2013, and had a wonderful time. The beds were comfortable and it was well stocked. Beach access was simple and the view, although from the side that included public beach access and parking lot, was still enjoyable. We never used the pool, although it appeared clean, because the beach was too wonderful to waste time at the pool:). The only things I would caution about: …

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    $200

    3 BR / 2 BA / Sleeps 8

    1 / 17

    $200

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    Quiet Palms

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    Quiet Palms 215 81st St. Holmes Beach, FL. 34217 The name says it all! Quiet palms resides on a docile street on Holmes Beach, just a few minutes walk from the white sandy beaches. This 3 bedroom, 2.5 bathroom Florida vacation home offers a lovely serene atmosphere. The very private backyard is embellished with…
    • Private Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $93

    2 BR / 2 BA / Sleeps 6

    9 Reviews

    $93

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    Terrace Condo 2

    2 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 9 Reviews

    Details

    Reviews

    (9)

    The Terrace Condominium #2, located at 3100 Gulf Drive in Holmes Beach is a beautifully and comfortably furnished, two bedroom, two bath town home condo with heated pool, private garage and three separate lanais. The pool area is beautifully landscaped with native plants and features a pergola and multiple seating …
    • 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

    (9)

    Very Good

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

    Good place, good price, good overall experience.

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    $165

    3 BR / 2 BA / Sleeps 8

    1 / 13

    $165

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    Mermaids Crossing

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    Mermaids Crossing 207 69th Unit B Holmes Beach, Fl. 34217 Mermaids Crossing is a cute-as-a-button newly renovated, ground level 3 bedroom and 2 bathroom private duplex that offers a private heated pool, lush tropical landscaping, fantastic furnishings and so much more! Centrally located on the Island, you are just …
    • 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

    1 / 26

    $250

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    Blue Heron

    4 BR / 3 BA / Sleeps 10 | Quick view

    Details

    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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    $425

    4 BR / 3 BA / Sleeps 8

    6 Reviews

    $425

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    La Plage 03

    4 BR / 3 BA / Sleeps 8 | Quick view
    “ Excellent ” 6 Reviews

    Details

    Reviews

    (6)

    L’Plage Condominium #3 located at 6420 Gulf Drive in the preferred northern end of Holmes Beach is a spectacular four bedroom, three bath Gulf front unit with a glorious beachside swimming pool and spa. There is even a BBQ area onsite for your use! L’Plage Condominium features a security gated entry, elevator and …
    • Waterfront
    • Ocean or water views
    • 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

    (6)

    Great Place

    Left on Apr 08, 2009 for a stay in March 2009

    We definitely enjoyed our stay! Out trip was a birthday celebration among friends. So having the 4br/3baths for 8 worked out wonderfully. The condo is beautiful and the location is great.

    Our only problem was figuring out the garage openers and then the code for the gate at the pool. We had 3 garage openers and none worked. We only parked once in the garage after somebody got out in the …

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    $250

    4 BR / 3 BA / Sleeps 10

    1 / 19

    $250

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    Island Retreat

    4 BR / 3 BA / Sleeps 10 | Quick view

    Details

    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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    $300

    5 BR / 4 BA / Sleeps 12

    1 / 30

    $300

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    Bayfront Paradise

    5 BR / 4 BA / Sleeps 12 | Quick view

    Details

    Bayfront Paradise 238 South Harbor Dr. Holmes Beach, Fl 34217 Bayfront Paradise is an absolutely stunning custom luxury home that is tucked away on a quiet residential street with the most amazing Bay views. As soon as you enter the property you are immediately immersed in the relaxing isle atmosphere of Anna Maria…
    • 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

    Details

    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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    $329

    4 BR / 3 BA / Sleeps 10

    1 / 26

    $329

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    Avalon

    4 BR / 3 BA / Sleeps 10 | Quick view

    Details

    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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    $165

    2 BR / 2 BA / Sleeps 6

    25 Reviews

    $165

    Inquire

    Gulf Sands 201

    2 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 25 Reviews

    Details

    Reviews

    (25)

    Gulfsands Condo #201, located at 4200 Gulf Drive in Holmes Beach, is a beautifully furnished two bedroom, two bath condo directly on the beach. It’s in a popular Gulf front complex with a large heated pool, elevator and undercover parking. This complex is located adjacent to the Manatee Public Beach to provide added…
    • 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

    (25)

    Outstanding Condo

    Left on Feb 23, 2009 for a stay in January 2009

    The condo, itself, is the nicest one we have stayed in. We have been coming to the island for 30 years and have stayed in a number of different condos.
    The only problem we had; and I assume that all has been completed; is that there was a lot of remodeling being done to the complex.
    The owner does an outstanding job in getting the condo ready for guests.
    When we return, and we will, we …

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    $150

    1 BR / 1 BA / Sleeps 4

    1 Reviews

    $150

    Book

    Coconuts Courtyard Unit 119 Upstairs

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

    Details

    Reviews

    (1)

    One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two double beds in …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Clothes Dryer
    • A/C or climate control
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Our 10th Year at the Wonderful Coconuts Beach Resort

    Left on Aug 10, 2014 for a stay in January 2014

    What can one say about the Coconuts Resort on Holmes Beach, FL. Well we have spent two months of every year for ten years there and expect to do so in 2015. They are a friendly management with Joyce & Kelly to respond to your needs. Plenty of fresh towels and supplies as you need. A weekly clean out and beds changed by an experienced cleaner. The unit has a 32 inch flat screen and full wireless …

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    $317

    4 BR / 3 BA / Sleeps 10

    4 Reviews

    $317

    Inquire

    FAIRWINDS

    4 BR / 3 BA / Sleeps 10 | Quick view
    “ Excellent ” 4 Reviews

    Details

    Reviews

    (4)

    Beautifully furnished 4 bedroom/3.5 bath home just a block to the beach! Large greatroom layout with four separate balconies, high ceilings, and tropical hardwood floors throughout. Master Suite on the main floor has large walk-in closet and ensuite bathroom with Jacuzzi soaker tub and separate shower. Very well-…
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (4)

    Love this house!

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

    Lovely, comfortable house with a great location. The pool was perfect ... We are going back next year!

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    $105

    1 BR / 1 BA / Sleeps 4

    15 Reviews

    $105

    Inquire

    Palm Cay 1

    1 BR / 1 BA / Sleeps 4 | Quick view
    “ Very Good ” 15 Reviews

    Details

    Reviews

    (15)

    Palm Cay Condominium #1 is located at 3000 Gulf Drive in Holmes Beach, on the west side of the street for easy beach access. The complex offers a heated pool and an on site coin operated laundry room for your convenience. It’s a short stroll to shopping and restaurants and the beach is less than two minutes away. …
    • 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

    (15)

    cozy, great location and affordable

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

    Nice home with a cozy feel. convienent location to beach and stores. Pool was clean and quiet. Nice layout and room to bq on side lawn. We rented bikes and biked the area never using our car. Clean, good size rooms and well kept property.Nice laundry area as well. Easy walk to the beach.
    The busy road was a bit of a draw back since our unit fronted the road.

    We would rent this unit again.

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    $137

    2 BR / 2 BA / Sleeps 4

    1 / 16

    $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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    $137

    2 BR / 2 BA / Sleeps 6

    1 / 20

    $137

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    Gulf Shores 106

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Gulf Shores #106 5616 Gulf Drive #106 Holmes Beach, FL 34217 Enjoy the beautiful, unobstructed views of the Gulf of Mexico from your living room, kitchen or dining room in this lovely Gulf front condo in Holmes Beach. Offering 2 bedrooms and 2 baths, this very spacious direct gulf front condo is ideal for a beach …
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $175

    2 BR / 1 BA / Sleeps 5

    1 / 11

    $175

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    Loggerhead Beach House

    2 BR / 1 BA / Sleeps 5 | Quick view

    Details

    Welcome to the Loggerhead Beach House on Anna Maria Island. This completely remodeled duplex is comprised of two stunning new beach homes that are close to the beach and in a quiet residential neighborhood. The Loggerhead Beach House side includes a private heated pool (not shared), hot/cold outdoor shower, lush …
    • Internet Access
    • Parking
    • Grill
    • Stereo or CD player
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $317

    4 BR / 4 BA / Sleeps 10

    1 / 26

    $317

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    BEACH BOUND

    4 BR / 4 BA / Sleeps 10 | Quick view

    Details

    Brand New Construction! Spacious Ground Level 4 Bedroom/4 Bath Home with One Car Garage, Heated Pool, and Hot Tub. Featuring Granite Countertops, Stainless Steel Appliances, and Flat Screens throughout. Great location in a quiet neighborhood, just a block to the beach, and close to the Trolley Stop. With 4 Bedrooms …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly

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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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      $124

      2 BR / 2 BA / Sleeps 6

      1 / 20

      $124

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      Sunset Beach

      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Sunset Beach 302 74th St. Holmes Beach, Fl. 34217 This cute island bungalow is just perfect for your laid-back Anna Maria retreat! Newly updated throughout, this 2 bedroom, 2 bathroom beach cottage is just a short 2-3 minute stroll over to the fabulous Gulf beaches. There is a private heated pool, full kitchen …
      • Heated Pool
      • High Speed Internet
      • Patio
      • Television
      • DVD Player
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $140

      2 BR / 2 BA / Sleeps 6

      7 Reviews

      $140

      Inquire

      Anna Cabana Beach House

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

      Details

      Reviews

      (7)

      The Anna Cabana Beach House is an adorable two bedroom, two bath home located at 3709 Gulf Drive in Holmes Beach. This quaint home has a large open deck with a great view of the beach. Watch the sunsets or enjoy the tropical landscaping on the large deck facing the Gulf. Numerous fruit trees and coconut palms surround…
      • 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

      (7)

      Beautiful retreat!!

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

      The bungalow is just perfect. Our family loved the location and the
      property was clean and beautiful. I only wish it was available when we
      return this June. Too bad for us!!! It's a place to dream of while back
      home in Illinois!!

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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

      PreviousNext property

      $414

      5 BR / 3 BA / Sleeps 13

      12 Reviews

      $414

      Inquire

      Valhalla Up and Down

      5 BR / 3 BA / Sleeps 13 | Quick view
      “ Excellent ” 12 Reviews

      Details

      Reviews

      (12)

      The Valhalla located at 3216 Gulf Drive in Holmes is a wonderful five bedroom, three bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect!Each unit features a large covered deck that is a …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Pet friendly
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (12)

      Wonderful Family Location

      Left on Mar 05, 2009 for a stay in July 2008

      Our extended family met here at the Valhalla. Accomodated 3 families plus a grandparent very comfortably. We used the uppper kitchen for family dinners and the lower kitchen for beach supplies, lots of waters, sodas, juices and snacks. Location is wonderful, units were clean and comfortable, low on a few kitchen supplies but not really a problem. The only think that I would mention is that …

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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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      $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

      PreviousNext property

      $135

      3 BR / 2 BA / Sleeps 6

      4 Reviews

      $135

      Inquire

      Palm Cay 5

      3 BR / 2 BA / Sleeps 6 | Quick view
      “ Excellent ” 4 Reviews

      Details

      Reviews

      (4)

      Palm Cay 5 located at 3000 Gulf Drive in Holmes Beach is a very spacious three bedroom, two bath town home located west of Gulf Drive for easy beach access. The complex features a very large heated pool and onsite laundry room. The complex is about one half block to the beach and is very convenient to shopping and …
      • 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

      (4)

      We had a wonderful stay, in a great location, and in a spacious

      Left on Jul 26, 2012 for a stay in July 2012

      We loved the rental property! It was very rencently renovated and the owners must take pride in their property, as they have selected stunning appointments, materials, and finishes for the unit, certainly blowing the majority of its competitors out of the water since most investors merely choose the cheapest and standard "rental" quality materials and finishes. The property is very spacious, …

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