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$118

3 BR / 2 BA / Sleeps 6

River Strand Private Pool Home - Anna Maria Island vacation rentals
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$118

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River Strand Private Pool Home

3 BR / 2 BA / Sleeps 6 | Quick view

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Beautiful lakefront home in exclusive River Strand gated community within Heritage Harbour. This bright designer styled home offers the highest standard for your stay in the Florida Sun Coast. Home has every amenity you would possibly need to make your time here a memoriable stay. The house has central air …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$140

3 BR / 3 BA / Sleeps 5

PalmaSola - Anna Maria Island vacation rentals
1 / 18

$140

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PalmaSola

3 BR / 3 BA / Sleeps 5 | Quick view

Details

A Great Beach Vacation spot, A Nice Comfortable 3 bedroom home,Close to beaches,, half mile from causeway, PalmaSola bay. Great spot to run & swim with your dogs. We are doing restorations & upgrades on our house, So it isn't magazine ready.It is a great location to escape to a place and enjoy warm weather, …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$275

4 BR / 3 BA / Sleeps 8

Bradenton Florida home - Anna Maria Island vacation rentals
1 / 21

$275

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Bradenton Florida home

4 BR / 3 BA / Sleeps 8 | Quick view

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Get away from the cold! Enjoy this comfortable, well appointed and luxurious 3500 sq. ft. home in the warm, sunny climate of Florida's Gulf Coast. This home is meticulously maintained and comfortably furnished with everything you will need to have a relaxing vacation in a quiet and secluded residential Florida …
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children

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$310

4 BR / 4 BA / Sleeps 8

7 Reviews

$310

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Sand Dollar

4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 7 Reviews

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Reviews

(7)

The Sand Dollar, located at 143 50th Street in Holmes Beach is a beautiful, newly constructed four bedrooms, three and one half bath home with a large heated pool surrounded by native landscaping. It’s located on a quiet residential street west of Gulf Drive and less than a two minute walk to the beach with no busy…
  • 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

(7)

Sand Dollar - excellent place to stay in October

Left on Oct 24, 2009 for a stay in October 2009

Nice house, very new, all there that is needed, nice garden and pool. Perfect for a family of 4 to 6. In house elevator available. No carpets, which for us was a very important aspect. Furniture overall a bit on the cheapy side (Ikea) but perfectly ok for our stay. Air conditioning in parents sleeping room too noisy and too strong, compared to other rooms. Big garage to park car inside.

In …

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$150

3 BR / 2 BA / Sleeps 8

2 Reviews

$150

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Caribbean Reef

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

Details

Reviews

(2)

Caribbean Reef 306 67th Street Unit A Holmes Beach, Fl 34217 Caribbean Reef is one side of a newly constructed private duplex and is embellished with its own private heated pool. This cute as a button 3 bedroom and 2 bathroom home is centrally located on the Island and is just a short 2.5 minute walk from the white…
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (2)

    Paradise

    Left on Sep 02, 2014 for a stay in May 2014

    We stayed at Caribbean Reef in May 2014. It was a amazing. The home was gorgeous and just a couple blocks from the beach. The house had almost everything you would need to just start relaxing! There were pool toys and beach items in the home. The home is beautifully decorated! The private pool in the back yard is amazing. Our family had a glorious and relaxing vacation! The company was …

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    $244

    3 BR / 2 BA / Sleeps 8

    BLUESKY - Anna Maria Island vacation rentals
    1 / 18

    $244

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    BLUESKY

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    Beautiful, Brand New, 3 bedroom/2 bath home with Heated Pool and Hot Tub! Granite Countertops, vaulted ceilings, Stainless Appliances, and more. Great location in a quiet neighborhood, just a couple blocks to the beach, and a half block to the Free Island trolley. Enjoy the pool and hot tub with the outside flat …
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly

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    $350

    6 BR / 4 BA / Sleeps 15

    1 / 35

    $350

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    Pearl Beach

    6 BR / 4 BA / Sleeps 15 | Quick view

    Details

    Pearl Beach 6906 Holmes Blvd. Holmes Beach, Fl. 34217 Pearl Beach is a brand new luxury Island home that features 6 bedrooms and 4.5 bathrooms and exudes luxury with its deluxe furniture, coastal decorations, gourmet kitchen and private heated pool with spa and waterslide! Ideal for larger gatherings, this home …
    • Heated Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $215

    3 BR / 2 BA / Sleeps 6

    1 / 19

    $215

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    The Reefs Edge

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    The Reef's Edge 3302 Gulf Dr. Apt 103 Holmes Beach, Fl. 34217 The Reef's Edge is a luxury 3 bedroom, 2 bathroom direct beachfront condo and is one of a select group of just five direct beachfront condos that makes up this exclusive property. It get's it name from the natural reef that is directly out front of …
    • Shared outdoor pool (unheated)
    • High Speed Internet
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $229

    3 BR / 2 BA / Sleeps 8

    1 / 31

    $229

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    Pool Home on a canal 1 mile to the beach!

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    This property is brand new to the rental market! Spectacular home in San Remo Shores, only 1 mile to the beach. This home has been remodeled with 3 bedrooms 2 baths and a amazing outdoor space, right on a canal to dock your boat if you wish, a inground pool, gas fire pit, 8 person jacuzzi, and a stunning outdoor …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Housekeeping Optional
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly

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    $300

    5 BR / 4 BA / Sleeps 12

    1 Reviews

    $300

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    Villa Marianne

    5 BR / 4 BA / Sleeps 12 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    Villa Marianne 111 Maple Ave. Anna Maria, Fl. 34216 Wow, you just can't say enough great things about this beautiful beach villa! This 5 bedroom, 4 bathroom home so close to the beach- no more than a 1 minute stroll and located on the prestigious North end of the island. Every room is exquisite- decorated to …
    • Outdoor Pool
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Awesome place to stay!!

    Left on Mar 22, 2015 for a stay in March 2015

    We just returned from our week long stay at Villa Marianne and couldn't be happier. We were two families- mine and my cousin and hers. 4 adults total, and 5 kids ages 8,6, 4,3, and 1. First of all, you are just a short walk to a lovely stretch of beach. At the end of the street there is a short path. And since it isn't a public access area, there aren't that many people- even during crowded …

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    $110

    2 BR / 1 BA / Sleeps 4

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    $110

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    Gulf Sound A

    2 BR / 1 BA / Sleeps 4 | 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 two bedroom one bath unit 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 trolley …
    • 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

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    $143

    2 BR / 1 BA / Sleeps 4

    1 / 11

    $143

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    Kims Kottage West

    2 BR / 1 BA / Sleeps 4 | Quick view

    Details

    Kim's Kottages West 205W 75th Street Holmes Beach, FL 34217 ISLAND DUPLEX-This totally updated 2 bedroom and 1 bathroom ground level duplex is just a short 2 minute walk away from the stunning white sandy beaches of the Gulf of Mexico. If you are looking for a quiet retreat away from it all than look no further. …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $145

    2 BR / 2 BA / Sleeps 4

    1 Reviews

    $145

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    Coquina Beach Club 203

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

    Details

    Reviews

    (1)

    Coquina Beach Club Unit 203 1906 Gulf Drive N. Bradenton Beach, FL 34216 Coquina Beach Club is a beautiful 2 bedroom 2 bath Gulf front condo with a heated pool and spacious floor plan. Gorgeous unobstructed view of the emerald Gulf water. All new furnishings and stainless steel appliances, granite counter tops, …
    • Shared outdoor pool (unheated)
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Loved this condo!!

    Left on Nov 01, 2014 for a stay in October 2014

    Stayed here for our girlfriends getaway and we all loved it. Perfect location, very quiet, great view of the gulf. The condo has everything you need for a relaxing stay. The color scheme is tranquil and the furnishings go perfectly for a beach place. The bed in the master bedroom is so comfortable and the closets are large.

    The only drawback were the stairs and taking our luggage up and down, …

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    $110

    3 BR / 2 BA / Sleeps 6

    1 Reviews

    $110

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    Immaculate Condo Exceptional Golf/Tennis Community

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

    Details

    Reviews

    (1)

    Luxurious fully furnished 3 Bedroom, 2 bath condo located on the 3rd floor end with a beautiful view of the golf course from the master bedroom, living room and screened in private balcony. If you enjoy tennis, golfing and fitness this condo can provide you with the perfect experience. It offers a 27 hole top rated …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - elevator access
    • Wheelchair accessible

    Details

    Reviews

    (1)

    Exceptional

    Left on Mar 01, 2015 for a stay in January 2015

    This is a very nicely furnished and clean new condo. Has all the accessories. The owners want this condo to feel like home. I definitely highly recommend renting here and give it the maximum stars.

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    $330

    5 BR / 3 BA / Sleeps 14

    1 / 24

    $330

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    Villa Del Sol

    5 BR / 3 BA / Sleeps 14 | Quick view

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    Villa Del Sol 211 Chilson Avenue Anna Maria, FL 34217 This is an exquisite, newly remodeled 5 bedroom, 3 bath ground level home with available boat dock. Inside the home you will find quality furnishings with a Caribbean decor. The open floor plan provides the perfect space for spending time together or …
    • Outdoor Pool
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $343

    4 BR / 4 BA / Sleeps 11

    2 Reviews

    $343

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    HAV'ANNA HIDEAWAY

    4 BR / 4 BA / Sleeps 11 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    When you 'have anna maria' on your mind, you'll want 'hav'anna hideaway' for your vacation home. This newly constructed 4 bedroom, 4 bath home is located just one short block to the beautiful and sparkling gulf beach. The main floor of the home consists of an open concept living room, kitchen with breakfast bar …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (2)

    Fantastic Family vacation

    Left on Aug 02, 2013 for a stay in June 2013

    We rented Hava'nna Hideaway in June 2013. It was the first family vacation for all ten of us. The house was very clean and roomy so we didn't feel hemmed in. We cooked most of our meals and used the BBQ grill outside a lot. It's about a block from the beach but they provide a beach wagon to haul your stuff. We loved the small pool outside and we used it a lot just sitting around talking and …

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    $241

    3 BR / 2 BA / Sleeps 8

    1 Reviews

    $241

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    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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    $156

    3 BR / 2 BA / Sleeps 6

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    $156

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    Dolphin House

    3 BR / 2 BA / Sleeps 6 | Quick view

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    Dolphin House 311 64th Street Holmes Beach, Fl. 34217 Nestled right in the midst of Anna Maria Island is this stunning 3 bedroom 2.5 bath townhome with private heated pool. Tropical landscaping abounds with a covered poolside patio. This island townhome offers great room and open kitchen area, large covered …
    • Outdoor Pool
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $115

    2 BR / 2 BA / Sleeps 6

    2 Reviews

    $115

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    Braden "River House"

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

    Details

    Reviews

    (2)

    This main house rental is located on a private cove of the Braden River. Beautiful views from living room and master bedroom and bath. This 2-story home has lots of space both indoors and out.Outdoor entertaining include a lap pool, fireplace, dining area and canoe. Perfect location, fenced yard for pet.
    • Waterfront
    • Ocean or water views
    • Shared outdoor pool (unheated)
    • Wireless Internet
    • Washing Machine
    • Pet friendly - ask
    • Suitable for children - ask
    • Suitable for the elderly
    • Wheelchair accessible

    Details

    Reviews

    (2)

    Well Appointed Quiet Home on River

    Left on Mar 22, 2015 for a stay in November 2014

    Really enjoyed this place for several reasons. First the location was outside the high traffic areas and close to Interstate. We played tennis at IMG academy not far from the house. My impression of the house was it was better than expected. High ceilings, big bathrooms and each room had a flat screen. The views of the river, wildlife and sunsets had me taking pictures everyday. The kitchen was …

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    $67

    3 BR / 3 BA / Sleeps 8

    6 Reviews

    $67

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    Cove at Sandy Pointe 111

    3 BR / 3 BA / Sleeps 8 | Quick view
    “ Very Good ” 6 Reviews

    Details

    Reviews

    (6)

    The Cove at Sandy Pointe 111, located at 3601 East Bay Drive in Holmes Beach is an exceptional three bedroom, three bath bay front unit. Located directly on the bay in a quiet location, this unit overlooks a natural mangrove preserve. The complex features a large heated pool.This spacious unit sleeps eight with a king…
    • 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

    (6)

    We had a wonderful time on anna Maria

    Left on Mar 14, 2012 for a stay in February 2012

    3 Bedrooms 3 baths, 3 balconies-what could be better for 2 couples sharing a relaxing month on anna Maria? Master bedroom is huge with a king bed and a pull out couch. Checkin was flawless and service was great-altho there were a few minor problems. Condo had not been cleaned as described, heat was off and then air conditioning needed service--this was taken care of immediately and did not …

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    $685

    9 BR / 6 BA / Sleeps 21

    1 / 59

    $685

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    The Blue Horizon

    9 BR / 6 BA / Sleeps 21 | Quick view

    Details

    The Blue Horizon 99 26th Street N. Bradenton Beach, Fl. 34217 9 bed luxury- Short stay fill in specials available for the fall! There is no more fantastic direct Gulf front luxury home than this. It simply has it all- newly constructed, exquisite 9 bedroom, 7.5 baths compound that will simply not disappoint. Two…
    • Private Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $219

    2 BR / 2 BA / Sleeps 4

    1 / 14

    $219

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    Island Paradise 4

    2 BR / 2 BA / Sleeps 4 | Quick view

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    Island Paradise #4 3708 Gulf Drive #4 Holmes Beach, Fl 34217 Island Living at its best! 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. This is as good as it gets! Beautiful 2 bedroom 2 …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $535

    8 BR / 6 BA / Sleeps 19

    1 Reviews

    $535

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    Summer House

    8 BR / 6 BA / Sleeps 19 | Quick view
    “ Very Good ” 1 Reviews

    Details

    Reviews

    (1)

    Summer House 211 54th St Holmes Beach, Fl 34217 Summer House is a brand new 8 bedroom and 6 bathroom rental home just completed and rental ready! The rental home has so many fun options for everyone- close to the beach, Gulf and Bay water views, table games, water slide, spa, roof top deck with hot tub (coming soon…
    • Heated Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Great for laid back vacation - Has it all

    Left on Dec 22, 2014 for a stay in December 2014

    Great house with heated pool, ping pong, pool table, hot tubs, etc.

    We had 9 people and plenty to spare.

    The kitchen is big, with plenty of dishes and bowls.

    The eating table can seat 12, which is one of the main reason we picked this property, as we only eat at the house, and we ate like kings.

    It is only 2 minutes to the beach, and a nice beach at that.

    I recommend it.

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    $117

    3 BR / 2 BA / Sleeps 6

    1 / 19

    $117

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    River Strand -Golf , Tennis, Sunsets and Beaches

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Gorgeous three bedroom , main level condo in the popular River Strand Golf and Country Club. Enjoy 27 holes of championship golf on the three courses, tennis on the Tru Har courts, an excellent fitness centre , resort style salt water pool with resistance lazy river and hot tub. The club house offers excellent …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Sauna
    • Wireless Internet
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $150

    2 BR / 2 BA / Sleeps 6

    2 Reviews

    $150

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    Hibiscus

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

    Details

    Reviews

    (2)

    Spectacular Bay Views!!! Overlooking the pool, this big water view will take your breath away! Relax on your covered lanai and gaze at the Sarasota skyline, watch the dolphins swim by, or swim in the pool while watching the sailboats drift by. This exceptional property is tucked away from the noise of the street and …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Thought this place would be great. It was AWESOME!

    Left on Jul 05, 2013 for a stay in June 2013

    Typically speaking, we rely on reviews on TripAdvisor to decide where to stay. We took a chance on this one because there weren't any reviews, yet. Wow - are we thrilled we did! It's even more beautiful and far more spacious than the pictures would have you believe. Just an outstanding place to stay and we can't wait to return. There is a lot to see and do all over Anna Maria Island, but this …

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    $236

    3 BR / 2 BA / Sleeps 8

    1 / 18

    $236

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    BEACHCOMBERS

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    Beachcombers is a spacious 3 bedroom/2 bath home with all of the "Old Florida Charm" you could ask for. Situated on Spring Avenue, just a couple of blocks to the Gulf of Mexico on Anna Maria's beautiful north end! Easy walking distance to many shops, restaurants, the Anna Maria City Pier and a short block to the free …
    • 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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    $229

    3 BR / 2 BA / Sleeps 6

    1 / 14

    $229

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    The Beach Front

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    The Beachfront 3302 Gulf Drive, Unit 101 Holmes Beach, FL 34217 This three bedroom, two bathroom direct Gulf front vacation property is one of a select group of just five beachfront condos, close to Bradenton Beach and the old fishing village of Cortez. Walk out on to your own beachfront balcony to watch the …
    • Shared outdoor pool (unheated)
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $95

    2 BR / 1 BA / Sleeps 6

    9 Reviews

    $95

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    Anna's Cottage

    2 BR / 1 BA / Sleeps 6 | Quick view
    “ Excellent ” 9 Reviews

    Details

    Reviews

    (9)

    Anna's Cottage, located at 105 3rd Street South in Bradenton Beach is a historic beach house located less than a five minute stroll to the emerald green water of the Gulf of Mexico. This refurbished cottage features a large open deck in the backyard with a gas BBQ grill and outside table. It’s a wonderful Bradenton …
    • Internet Access
    • Grill
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (9)

    Wonderful

    Left on Mar 25, 2010 for a stay in January 2010

    Every time we experienced a problem they were quick to react. The location made everything easy to get to. Look forward to staying next year.

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    $100

    2 BR / 3 BA / Sleeps 8

    9 Reviews

    $100

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    Bollinger Duplex, A

    2 BR / 3 BA / Sleeps 8 | Quick view
    “ Very Good ” 9 Reviews

    Details

    Reviews

    (9)

    The Bollinger Duplex, side A is a very comfortably furnished and spacious duplex apartment located at 6909 Gulf Drive in the preferred, quiet area of northern Holmes Beach. This property is located about one-half block to beautiful Gulf of Mexico where you can walk for miles in either direction on the white, sandy …
    • Internet Access
    • Grill
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (9)

    Close to the Beautiful Gulf

    Left on May 28, 2009 for a stay in May 2009

    The duplex we rented was spacious and very comfortable and was just a very short walk from the Gulf of Mexico. I did have a few issues, though. We came in expecting to have available to us for our use things like paper towels, toilet paper, garbage bags, and plastic containers in which we could store leftovers after meals. None of these items were available and had to be purchased by us after we …

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    $171

    2 BR / 2 BA / Sleeps 6

    4 Reviews

    $171

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    Island Oasis: 2BR Canal Home with Pool and Dock

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

    Details

    Reviews

    (4)

    Come and enjoy your own private Island Oasis! Located on the north end of Anna Maria Island in the city of Anna Maria, one block from the bay and a few blocks from the City Pier, this charming vacation rental will allow for some serious relaxation. This home-away-from-home offers two bedrooms and two baths, with a …
    • Waterfront
    • Spa/Whirlpool
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children - over five
    • Suitable for the elderly

    Details

    Reviews

    (4)

    Best Stay Yet!

    Left on Jul 11, 2013 for a stay in May 2013

    We were lucky to find Island Oasis. The wife and I have visited Siesta Key and anna Maria Island several times. This was the best stay yet. We caught snook across the bay in Perico Bayou and grouper at Longboat Pass. The backyard pool is the nicest and being able to hop in the boat and to the beach is just wonderful.

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    $175

    2 BR / 2 BA / Sleeps 4

    1 / 15

    $175

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    Windsong Cottage

    2 BR / 2 BA / Sleeps 4 | Quick view

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    Windsong Cottage 119 Beach Avenue Anna Maria, Fl 34216 Windsong Cottage is a charming 2 bedroom 2 bath elevated home just five houses from the Gulf. It has an open floor plan with new, comfortable furnishings that make you feel *right at home*. The plantation shutters add to that "Old Florida" charm. You won'…
    • Outdoor Pool
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $83

    1 BR / 1 BA / Sleeps 2

    1 / 24

    $83

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    Aggie's Place: 1BR Perfectly-Priced Duplex

    1 BR / 1 BA / Sleeps 2 | Quick view

    Details

    If you are looking a place to rest your head so you can enjoy Anna Maria Island to its fullest, then this is the place for you! With 400 square feet, this cute, one-bedroom Holmes Beach duplex provides enough space for anyone who just needs a quick getaway. Just a short walk to the white sand beach and sparkling …
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Patio
    • Suitable for the elderly

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    $171

    3 BR / 2 BA / Sleeps 6

    5 Reviews

    $171

    Inquire

    Coastal Cottage: 3BR Pet-Friendly Pool Home

    3 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 5 Reviews

    Details

    Reviews

    (5)

    The adorable Coastal Cottage, located in the laid-back city of Anna Maria, is the perfect place to take a totally carefree vacation. The white sand beach of Anna Maria Island and the azure blue waters of the Gulf of Mexico are only a short stroll from this delightful three-bedroom, two-bath vacation rental. An open …
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Patio
    • Suitable for children - over five
    • Suitable for the elderly

    Details

    Reviews

    (5)

    Coastal Cottage

    Left on Jul 25, 2013 for a stay in February 2013

    We loved the location. We enjoyed the house, but we did not know it was up for sale until we pulled in the driveway. We had too many requests for viewing which disturbed our visit enough that we decided not to book with you again next year.

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    $200

    2 BR / 2 BA / Sleeps 6

    4 Reviews

    $200

    Inquire

    Starfish Dreams: 2BR Canal Home w/Dock and Pool

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

    Details

    Reviews

    (4)

    Starfish Dreams is the perfect place to start your vacation! This family-friendly vacation rental is centrally located on Pine Avenue in the city of Anna Maria on Anna Maria Island, halfway between the Gulf of Mexico and Tampa Bay. If that were not enough, it also has a heated pool and is on a canal. This two-…
    • Waterfront
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Suitable for children - over five
    • Suitable for the elderly - ask

    Details

    Reviews

    (4)

    Magnificent property in fantastic spot on Anna Maria

    Left on Jun 14, 2013 for a stay in May 2013

    This was the best holiday rental (sorry Sue) we've ever had. Right in Pine Street, where all of the boutiques and local stores are, but within 100 yards of the beach and City Pier. Fantastically appointed, with excellent quality of all the equipment, this is a really, really comfortable and well situated property.

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    $100

    2 BR / 2 BA / Sleeps 4

    2 Reviews

    $100

    Inquire

    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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    $145

    4 BR / 2 BA / Sleeps 8

    2 Reviews

    $145

    Inquire

    Whispering Winds

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

    Details

    Reviews

    (2)

    Whispering Winds 210 Sycamore Avenue Anna Maria, Fl 34216 Key West style 4 bedroom, 2 bath home just a short walk from the Gulf of Mexico. This home offers private heated pool, three covered decks overlooking pool, BBQ grill, two car garage, cathedral ceilings, tile, carpet, open floor plan with large kitchen…
    • Outdoor Pool
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (2)

    Can't wait to go BACK!

    Left on May 13, 2014 for a stay in March 2014

    We stayed at Whisper Winds,3 houses to the wonderful White Sand... Great house with 4 bdrm ,heated pool, great location with plenty of room for Family Vacation.. This is our 2nd trip to AnnaMaria. So many quaint shops,be sure you visit the fresh donuts shop..get their early their worth the wait. The north end is great if your traveling with small kids. Bring your bikes or rent them their.. So …

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    $142

    2 BR / 2 BA / Sleeps 6

    1 / 12

    $142

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    Tropical Sunset 4

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Tropical Sunset #4 3311 Gulf Drive #4 Holmes Beach, Fl. 34217 Enjoy Tropical Sunsets from this lovely two bedroom two bath third floor condo, appropriately named, and only 57 steps from beautiful Gulf of Mexico. Views of the sparkling waters from private enclosed glass/screen lanai off living room and master …
    • Outdoor Pool
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $229

    4 BR / 3 BA / Sleeps 8

    2 Reviews

    $229

    Inquire

    ENDLESS SUMMER

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

    Details

    Reviews

    (2)

    Beautiful, completely remodeled, ground level 4 bedroom/3 bath Home in a quiet neighborhood located just over a block to the beautiful white sand gulf beach. Close to shops and restaurants, and just a short block to the free trolley stop. Within an easy walk of Hurricane Hanks, A Moveable Feast,The Eat Here Restaurant…
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (2)

    Wow

    Left on Jun 20, 2014 for a stay in April 2014

    All I can say is that this house had the wow factor (for us), it was almost perfect.

    The layout of the house was great, it was fully fitted out and had everything we needed.

    The fenced off pool was great was we had small children, with outside space was really nice, especially having a lawn rather than concrete it allowed the children to play outside whilst we did other things - the almost …

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    $171

    3 BR / 2 BA / Sleeps 8

    1 Reviews

    $171

    Inquire

    Island Hideout West: 3BR Family-Friendly Pool Home

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

    Details

    Reviews

    (1)

    This elevated vacation rental has been newly renovated to meet your high standards of vacation home living. With over 1400 square feet of living space, this home boasts three large bedrooms with a king master suite, a queen in the second bedroom, and a twin in the third. A queen sofa bed in the living area provides …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • A/C or climate control
    • Porch
    • Suitable for children - over five
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Perfect!!!

    Left on Jun 16, 2014 for a stay in June 2014

    The hide out west was awesome! We took our kids, grandkids and parents. We couldn't

    have picked a more perfect rental!

    I even realized after I was on my way home, I had left my medications and my jewelry behind.....Tura and Sabrina were amazing as they took care of retrieving my belongings and sending them overnight to my home.We are already looking at dates for our next visit to the hide out!

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    $350

    3 BR / 2 BA / Sleeps 6

    1 / 22

    $350

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    LaPlage 7

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    La Plage Unit # 7 6424 Gulf Dr. Unit #7 Holmes Beach, Fl. 34217 La Plage, unit # 7, it just does not get any better than this direct Gulf front, 3rd floor corner unit. Located in the prestigious La Plage condominium complex, this unit has it all. These luxury Mediterranean style condos are huge- almost 2300 sq. …
    • Shared outdoor pool (unheated)
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $125

    3 BR / 2 BA / Sleeps 10

    1 / 22

    $125

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    Palm Haven, 3 bedroom

    3 BR / 2 BA / Sleeps 10 | Quick view

    Details

    This beautifully decorated 2 bedroom, 1 bath and 3 bedroom, 2 bath duplex is just a short half block from the white sand beaches of Anna Maria Island. The 2 bedroom unit sleeps 7 people and the 3 bedroom sleeps up to 10 people. Palm Haven is the perfect vacation spot for anyone! Amenities Include: Full kitchen, …
    • Sauna
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

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    $350

    5 BR / 4 BA / Sleeps 12

    1 / 28

    $350

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    Villa La Concha

    5 BR / 4 BA / Sleeps 12 | Quick view

    Details

    Villa La Concha 113 Maple Avenue Anna Maria, Fl 34216 Villa La Concha is a stunning brand new elevated and luxury Island home located on the prestigious Northern end of Anna Maria Island. This lovely home is located West of Gulf Drive and just 1 minute stroll down the street from a direct beach access to the Gulf …
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $215

      3 BR / 2 BA / Sleeps 8

      1 / 22

      $215

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      Sandcastle 3

      3 BR / 2 BA / Sleeps 8 | Quick view

      Details

      Sandcastle 3, located at 200 Gulf Drive North in Bradenton Beach, is an exquisite three bedroom two bath gulf front condo luxuriously decorated with a tropical flair. Enjoy panoramic views of the Gulf of Mexico and Bridge Street. Stay in the midst of Bradenton Beach’s historical district where Key West style shops …
      • 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

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      $379

      6 BR / 3 BA / Sleeps 17

      1 / 30

      $379

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      Grande Haven

      6 BR / 3 BA / Sleeps 17 | Quick view

      Details

      Grande Haven 804 North Shore Dr. Anna Maria, Fl. 34216 Grande Haven is a spectacular example of high architecture, fine design and custom finishing at its best. This home was designed by the award winning Gene Leedy, combining the use of pre-stressed concrete, contemporary architecture and a splash of British East…
      • High Speed Internet
      • Patio
      • Television
      • DVD Player
      • Suitable for children - ask
      • Suitable for the elderly - ask

      PreviousNext property

      $300

      3 BR / 3 BA / Sleeps 6

      14 Reviews

      $300

      Inquire

      Bradenton Beach Club D

      3 BR / 3 BA / Sleeps 6 | Quick view
      “ Excellent ” 14 Reviews

      Details

      Reviews

      (14)

      The Bradenton Beach Club Unit D, located at 1700 Gulf Drive is a luxury gulf-front complex featuring an elevator, two heated pools, spa and bayside gazebo. This is a premier Bradenton Beach rental property! This spacious condo has panoramic beach views yet just across the street is a boardwalk meandering through the …
      • 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

      (14)

      Excellent Ocean-Front Property

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

      This is a beautiful 3BR condo on the beach. The beachside pool is down the stairs below the unit. We found the unit itself to be updated, clean, and private. The screened-in lanai is fabulous (we enjoyed many sunsets here). Also, you can hear the surf at night from the master bedroom. There is parking under the building, and an elevator from the garage. We plan to stay here again on our …

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      $171

      2 BR / 2 BA / Sleeps 6

      1 / 17

      $171

      Inquire

      Tiffany Place 205

      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Tiffany Place #205 7000 Gulf Drive #205 Holmes Beach, Fl. 34217 There is plenty to do while staying at Tiffany Place. Walk the white sandy beach and shell hunt or just relax and listen to the beat of the waves while you soak up the sun with a good book and there is always great shopping nearby It is a quiet …
      • Shared outdoor pool (unheated)
      • Internet Access
      • Dishwasher
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $120

      2 BR / 2 BA / Sleeps 4

      7 Reviews

      $120

      Inquire

      Bridgeport Condo 101

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

      Details

      Reviews

      (7)

      Bridgeport Condo 101, located at 501 Gulf Drive North in Bradenton Beach is a spacious two bedroom, two-bath condo with an elevator, undercover parking and large heated pool. You can enjoy Gulf views from virtually every room. Bridgeport Condo is a great Bradenton Beach rental property!This beautiful unit features all…
      • 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

      (7)

      Tickled pink

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

      We were tickled pink to rent this condo over the July 4th weekend!! It usually rents for a week at a time, but since it was still vacant they made an exception for a partial week. We had a GREAT GREAT GREAT time and would love to return there!!! The condo was spotlessly clean and spacious, just as depicted in the photos and narrative. There were plenty of towels, utensils, cookware...even hand …

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      $300

      6 BR / 3 BA / Sleeps 12

      1 / 25

      $300

      Inquire

      Angel Sea

      6 BR / 3 BA / Sleeps 12 | Quick view

      Details

      Angel Sea 4118 5th Avenue Holmes Beach , FL 34217 Take a look at this moderately priced 6 bedroom luxury villa only a few minutes stroll to the beach! In certain parts of the world, the Mediterranean is a byword for family vacations in the sun, relaxing, and taking a break from the stresses and strains of modern…
      • Private Pool
      • High Speed Internet
      • Patio
      • Television
      • DVD Player
      • Suitable for children - ask
      • Suitable for the elderly - ask

      PreviousNext property

      $125

      2 BR / 1 BA / Sleeps 6

      20 Reviews

      $125

      Inquire

      Anna Maria Beach Place, Unit 1

      2 BR / 1 BA / Sleeps 6 | Quick view
      “ Very Good ” 20 Reviews

      Details

      Reviews

      (20)

      Anna Maria Beach Place #1, located at 201 35th Street in Holmes Beach is a charming beachside complex featuring six units surrounding a heated pool and tropical gardens. Immediately across a rarely traveled, dead end road are the white sandy beaches and the emerald green water of the Gulf of Mexico. It doesn't get …
      • 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

      (20)

      Great except furnishings

      Left on Apr 06, 2009 for a stay in March 2009

      Location perfect, overall building great.
      Furnishings in our 2 bdrm unit #1 were very worn, almost shabby. Bedding was also way past it's prime.

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      $250

      5 BR / 3 BA / Sleeps 12

      1 / 20

      $250

      Inquire

      Villa Portofino

      5 BR / 3 BA / Sleeps 12 | Quick view

      Details

      Villa Portofino 4112 5th Ave. Holmes Beach, FL 34217 Villa Portofino- it defines Anna Maria Island luxury. This upscale 5 bedroom, 3.5 bathroom Mediterranean Villa is only a short 3 minute walk from the beautiful white sand beaches. There is a walk-in heated swimming pool with waterfall. Also, the kids will …
      • Outdoor Pool
      • Internet Access
      • Dishwasher
      • Suitable for children - ask
      • Suitable for the elderly - ask
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