Vacation Rentals & Beach Rentals in Anna Maria Island

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1,337 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!

Match: Iron Wheelchair adapted

All filters match

Price per night from

$286

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White Sands Village - Unit 112

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$125

White Sands Village - Unit 618

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$164

Charming Private Studio in Historic Downtown Area

Sarasota studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$258

Tropic Terrace #3 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$118

Harbor Towers

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$138

4 Bed 3bath Water front home

Sarasota house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$436

Tropic Terrace #18 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$117

Tropic Terrace #32 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$166

Tropic Terrace #40 - Beachfront Resort

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$209

Tropic Terrace #37 - Beachfront Resort

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$155

Tropic Terrace #41 - Beachfront Resort

Treasure Island condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$185

Tropic Terrace #35 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$155

Tropic Terrace #15 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$118

Tropic Terrace #44 - Beachfront Resort

Treasure Island condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$166

Tropic Terrace #48 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$118

Tropic Terrace #29 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$237

Tropic Terrace #49 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$117

The Country Inn: spacious 1 bedroom w sofa bed, shared pool centrally located

Pinellas Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$114

Stay near the heart of Sarasota

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$115

Luxury Village Townhouse w/ Gulf and Beach Views

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“A wonderful home in an equally wonderful location.” The home provides a truly enjoyable family situation. The quality of the furnishings is very nice, the living space is very well maintained and clean and my interaction with the owner was always timely and courteous. My wife and I shared the home with our 14 year old granddaughter during our stay and the quiet enjoyment of the pool and the easy 1-2 minute walk to the Gulf of Mexico and the 5 minute walk to the heart of Siesta Key Village made the location hard to beat. Except for our day trips no car was needed. This is our second stay in the home and we will look to reserving it for our next visit. There were absolutely no disappointments only wonderful experiences.

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$659

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“It was wonderful!” Everything about the trip and condo was great! Mike met us to give us the keys and we called him for suggestions about restaurants, etc. and he was very helpful. The condo was very clean and had everything we needed. It was also great that we were able to use the beach chairs and umbrella. I am already trying to figure out when we can go again.

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$163

“gracious and spacious” Lovely home and great location to walk throughout Siesta Key Village and the beautiful sands of the beach!! We were able to have everyone together for a great vacation.

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$148

SunWay Suites Unit 1 Sandpiper

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$149

Kima 503 Madeira Beach Front 2bd/2bath Condo Top Floor WHITE SANDY BEACHES!

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful !!!” I never know from the pictures posted when they were taken and the true condition of the home. With this property we were not disappointed. We took beach chairs, towels and all of that was provided at the house. The house was clean and just as pictured. The only thing that I can suggest is knife's for the kitchen. There are towels and lines galore. and the location was good. Close to all we wanted to do but quiet as we wanted it to be. The house has an apartment upstairs that we rented for our son and it worked out great. Plenty of room. No fighting for bathroom time to shower. There was 7 of us and we have already voted on this property for our next years trip to the beach...

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$221

Water View, 100 Fishing Dock! Teton 40 Ft. Trailer W/3 Slide Outs

Palmetto house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$138

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 57 minutes

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$194

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$305

Private modern 3BR home, salt water pool

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$344

SunWay Suites Unit 3 Seagull

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$149

Beachfront Madeira Beach - Across from Johns Pass!

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$455

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$46

Sunset Beach Bungalow

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$148

Sunset Beach Cottages, 1 Bedroom Beach Cottages

Treasure Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$241

House of Blues - Lovely 2-Bedroom Condo with Pool, W&D and Patio

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$201

Sunshine Paradise at Redington Beach

Redington Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$229

Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$290

Beachfront Studio Condo. Heated Pool. Perfect Views From Private Balcony.

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 minutes

1 of 2 match: Wheelchair adapted, Iron

1 of 2 filters match

Price per night from

$166

Viewing 38 of 1,337
rentals in Anna Maria Island

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