Vacation Rentals & Beach Rentals in Anna Maria Island

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142 beach rentals

Luxury Penthouse Condo Overlooking Beach/Gulf

Treasure Island apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Review” The place was amazing! Perfect weather and a great week! Thank you so much for the opportunity! We had the best week!

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Price per night from

$286

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Island Village Hideaway! Steps to Sand

Longboat Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$193

Shorewalk waterfront Condo Bradenton

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Nice and affordable condo convenient to shopping and restaurants.” This unit has been updated and is a very comfortable place to stay. The owner responded promptly when we contacted him.

Responds fast! avg. 2 hours 1 minutes

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$95

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$295

NEW! Staying with friends or family? Ask them to rent you a GuestWing!

St. Petersburg caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$205

Beachfront view, toes in the sand and gulf. Simply paradise, book now your beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 16 minutes

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$275

Luxury Beach Condo built 2023

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$343

Beautiful Location On Bay Side, Water View, Pool

Sarasota villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$229

Nice mobile home by the canal

St. Petersburg house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$95

The Sand Dollar: Historic Charm Meets Beach Chic in the Waterfront District

Gulfport apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$126

Paradise Lane- Dolphin View on the Intercoastal Water !! Boats Welcome

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$482

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$409

Waterfront Condo with fishing & boat docks

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 20 minutes

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$182

John's Pass-Time Beach Front Cottage

Madeira Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$287

Piece of Paradise on Beautiful Anna Maria Island VRC 20-000087

Holmes Beach villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$148

Executive Waterfront Home

St. Petersburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Wheelchair adapted, Stereo system

1 of 2 filters match

Price per night from

$258

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$716

Responds fast! avg. 4 minutes

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$139

Private, Family Friendly Home, 10 min to Beach

Bay Pines house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$212

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$161

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$516

Charming 1 Bedroom Condo on Gulf of Mexico Beach

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$287

BEACH FRONT CONDO *** MADEIRA BEACH

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$368

3 Bed/2 Bath Handicap Madeira Beach Gulf side Condo w/ Heated pool and Spa

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Wheelchair adapted, Stereo system

1 of 2 filters match

Price per night from

$344

Treasure Island Beach Condo

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 45 minutes

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$155

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$999

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$115

Five star Downtown Sarasota tropical garden Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Paradise Found in Downtown Sarasota” Absolutely charming, fully redone/ upgraded bungalow close to everything Sarasota has to offer. This was the third year running my wife & I have stayed at the wonderful home located minutes from Sarasota's best beaches, restaurants & shopping. We fully intend to return again next year! The two bedroom home is in pristine condition. Beautifully decorated, lovely hardwood flooring throughout with a fully stocked (appliances, crockery, pots/pans, cutlery, etc...) kitchen & renovated bathroom. Everything you need is provided, just arrive & settle-in. A huge projection screen in the living room, should you want to have an at-home movie night (rental Dvd's a 5-minute walk away @ Publix). There's also a regular flat-screen TV in the living room, as well as a wall-mounted TV in the bedroom. The backyard is, personally, my favourite part of the home. A screen-in lanai to eat in & a beautifully manicured backyard to relax in under the tiki hut or under the palm trees. There are a few seating areas throughout the backyard. Find the space you like the best, sit-back & relax with a cool cocktail- very civilized & very beautiful. You'll feel like you're in the Caribbean, not Florida in this backyard. Maureen & Pat, your hosts who, very conveniently, live right next door have provided everything you need, including all the beach chairs, umbrellas, beach towels, etc...to take along with you to Sarasota's beautiful beaches. Maureen has also provided tons of literature about the area in the house- restaurant menus, local mags, maps- everything. Maureen & Pat are always happy to suggest restaurants, beaches, shopping, golf, etc. They know Sarasota well, are friendly & happy to help in any way they can to ensure you have a wonderful stay. My wife & I can honestly say we love this property, have encountered no negatives about the place in three years of week-long stays & look-forward to our time there each year. We recommend this lovely home to everyone.

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$189

Excellent Location - Gulf/Beach View - Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 38 minutes

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$344

Luxury Water Front Condo - Intercoastal Waterway

Treasure Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Exceptional” We just returned from a 4 week stay at another/similar condo in this same building, same owner. The unit was clean, comfortable, spacious and located in close proximity to everything we needed (i.e. Beach, supermarket, restaurants, shops). John (owner) was more than accomodating with helping us get online (wifi) and being flexible with our schedule. The Gulf view was great and the building was relatively quiet considering it was Spring Break month. Will definitely be returning.

1 of 2 match: Wheelchair adapted, Stereo system

1 of 2 filters match

Price per night from

$240

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$310

Dolphin House at Gulfport's Pier

Gulfport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great time at Dolphin House” We went to Florida for my brother's wedding and needed to find a place to stay that would accommodate 7 people (2 kids included) and this was perfect. The bedrooms were a great size; very clean; the house is laid out nicely so that you are not all grouped together. There are two living rooms with TVs which helped our family so we weren't on top of each other the entire trip. We went over 4th of July weekend and the location ended up being perfect. We walked 2 mins down to the beach and watched an amazing fireworks display! It was also a close drive to St. Pete beach where my brother was staying. Overall, great experience.

1 of 2 match: Wheelchair adapted, Stereo system

1 of 2 filters match

Price per night from

$201

Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Amazing!” I stayed here with my husband and we had a great time! We were in Orlando visiting family and we decided to arrange some us time. The condo was excellent and very clean! Kathy and her husband were very informative, respond quickly,and available when we needed them. What was great was that we had all beach items available to us and were very useful. We were in close proximity to everything and the beach and restaurants were great! Everyone in the area was very friendly and my husband and I want to definitely come back!

Responds fast! avg. 1 hour 14 minutes

1 of 2 match: Wheelchair adapted, Stereo system

1 of 2 filters match

Price per night from

$224

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 22 minutes

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$196

Condo on the Key

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

“Immaculate” I had a wonderful stay at the condo in the key. Robin was easy to work with and always responsive. The condo was very clean and well stocked. If you are looking for a place where you can lay back and relax this is a nice condo. I loved that it's in a gated area.

1 of 2 match: Wheelchair adapted, Stereo system

1 of 2 filters match

Price per night from

$207

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

1 of 2 match: Wheelchair adapted, Stereo system

1 of 2 filters match

Price per night from

$258

Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

1 of 2 match: Wheelchair adapted, Stereo system

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Price per night from

$165

ISLAND TOWNHOUSE - 200 Steps to the BEACH

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 43 minutes

1 of 2 match: Wheelchair adapted, Stereo system

1 of 2 filters match

Price per night from

$207

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rentals in Anna Maria Island

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