Vacation Rentals & Beach Rentals in Anna Maria Island

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996 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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203 PERIWINKLE - PRETTY PALMS

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$553

A Gulf Front Paradise ! Newly updated , wide open wall to wall view, spacious cl

Bradenton Beach condo

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 16 minutes

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$458

Beautiful Beachfront Condo on the FL Gulf Coast

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful family beach vacation condo” The condominium is a great place to stay. All the amenities you need to enjoy a relaxing family vacation. There is an picturesque view of the beach on the balcony and a large pool to enjoy. The location of the condo is convenient to shopping and restaurants. Carol (the owner) is always very helpful and accessible if you have any questions about your stay. We have found a new place to stay on our summer vacation and can't wait to visit again next year!

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$241

Beachside Efficiency in Treasure Island (Blue)

Treasure Island apartment

  • 1 bathroom
  • sleeps 2

“Perfect location” The location of this stay is just amazing for the price. It's not directly on the beach but it practically feels like it is because there it is less than one minute to get to the beach without crossing any major road. The place is small, but it worked perfectly for just 2 people. Doesn't have a stove or oven so you have to resort to fruits or microwave food but it's not a big deal as there are tons of restaurants nearby. Only issue we really had was that you could hear either the neighbors next door or the above us running around and banging but it wasn't for too long and wasn't too bad. We had ignored it pretty quickly if that helps. For longer stays, be sure to get toilet paper and possibly soap. Also there is no way to wash clothes so pack a lot if this is your only stay. I don't believe there was an outdoor shower to wash off the sand before going in, but honestly we could have just missed where it was. Overall, really nice place, can't beat the price for the location.

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$86

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, Clothes dryer

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Price per night from

$163

Private modern 3BR home, salt water pool

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$345

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 46 minutes

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$194

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, Clothes dryer

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Price per night from

$222

Madeira Towers 302 Beachfront 3 bedroom 2 bath at Madeira Towers

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$388

Beach condo

Longboat Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$517

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$46

Pass-A-Grille Beach House

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$218

Sunset Beach One Bedroom Gulf View

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$230

AMAZING LOCATION ! direct across ST, from beach

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 0 minutes

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$167

Directly across the street from the Beach ! Unit #3

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 0 minutes

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$167

Directly across the street from the beach ! Unit # 4

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 0 minutes

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$167

New Listing PERFECT LOCATION ! Unit # 5

St. Pete Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 0 minutes

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$201

🏝Paradise on the Sarasota Bay, Close to Gulf Beaches🏝 (Sarasota)

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$194

Blue Heron Inn: 1/1 Spacious Apartment, 15 mins to beaches, pet friendly

Oneco apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$127

St Pete Beach fun in sun!

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$155

The Coconut on St Pete Beach - private pool - walk to water and dining!

St. Pete Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$195

Beautiful Condo near Anna Maria Beaches & IMG Academy

South Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Clothes dryer

1 of 2 filters match

Price per night from

$123

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Clothes dryer

1 of 2 filters match

Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$490

Cute 1 bedroom - 5 min Walk to Beach

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Wheelchair adapted, Clothes dryer

1 of 2 filters match

Price per night from

$241

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$138

Renovated 1BR Haven - 2 Mins from Sunset Beach!

Treasure Island house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Wheelchair adapted, Clothes dryer

1 of 2 filters match

Price per night from

$205

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Clothes dryer

1 of 2 filters match

Price per night from

$489

Beachfront Madeira Beach - Across from Johns Pass!

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Clothes dryer

1 of 2 filters match

Price per night from

$455

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, Clothes dryer

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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, Clothes dryer

1 of 2 filters match

Price per night from

$229

Trendy 4bd3bath Home in St Pete Arts District

St. Petersburg house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Wheelchair adapted, Clothes dryer

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Price per night from

$207

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, Clothes dryer

1 of 2 filters match

Price per night from

$241

The Moon Garden Apt at Crescent Lake

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Clothes dryer

1 of 2 filters match

Price per night from

$161

The Loft at Crescent Lake

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Clothes dryer

1 of 2 filters match

Price per night from

$132

Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Clothes dryer

1 of 2 filters match

Price per night from

$290

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, Clothes dryer

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Price per night from

$659

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