Vacation Rentals & Beach Rentals in Anna Maria

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100 beach rentals

Match: Wheelchair accessible

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Price per night from

$790

Experience the luxury of private beach living with TWO heated pools!

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Wheelchair accessible

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Price per night from

$1,151

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Wheelchair accessible

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Price per night from

$629

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Wheelchair accessible

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Price per night from

$1,944

Modern home with Private pool, walk to the beach, Putting green & Ping pong

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Wheelchair accessible

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Price per night from

$911

Great rentals within 20 miles that match your search

Fine Waterfront Living . Steps to Beach

St. Pete Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Wheelchair accessible

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Price per night from

$486

4 Minutes From Beach, Beds for 6!

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$104

Beautiful Island on Boca Ciega Bay & The Beach

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$115

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

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Wheelchair accessible

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Price per night from

$343

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Wheelchair accessible

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Price per night from

$998

Land's End: Gulf-front Luxury, WIFI, HDTV

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$393

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$127

TROPICCAL, 4 min from the beaches! Meticulously cleaned and sanitized!

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

“Lovely home in an awesome location!” Literally a minute's drive from the beach, this very clean and welcoming home is also convenient to great restaurants and shopping opportunities. It really is in a perfect location, especially considering the affordable price. Walking to restaurants and a rental shop is easy thanks to the sidewalk on Cortes. We even enjoyed a morning run to the beach - biking to the beach would also be a great option (3.5 mi one way.) The home might appear small at first, but we fit 6 comfortably, including 4 teenagers! The best part is the lovely décor that greets you after a long day at the beach or running around. Two thumbs up!

Responds fast! avg. 2 hours 33 minutes

Match: Wheelchair accessible

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Price per night from

$143

Lovely one story home on the water

Palmetto house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$458

Little Palms Villa. A lakeside home with style.

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.

Match: Wheelchair accessible

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Price per night from

$195

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Best home away from home at the beach.” I spent a lot of time searching for a bungalow at the beach and my expectations were surpassed when I opened the door! The owners were thoughtful in design, layout and furnishings to provide a laid back experience at the beach. I wished I could have stayed forever - it was that nice. I especially enjoyed the fully stocked kitchen which included colorful dishes to match the colorful walls and great blue floor! Best of all - location - you can walk everywhere as you are right in the historic Bridge Street neighborhood.

Match: Wheelchair accessible

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Price per night from

$245

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.

Match: Wheelchair accessible

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Price per night from

$239

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: Wheelchair accessible

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Price per night from

$285

Sea Breeze 108 (Madeira Beach) Beautiful, Tranquil Beach Front Condo

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 33 minutes

Match: Wheelchair accessible

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Price per night from

$246

Anna Maria The Pink Flamingo

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 41 minutes

Match: Wheelchair accessible

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Price per night from

$458

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.

Match: Wheelchair accessible

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Price per night from

$206

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!

Match: Wheelchair accessible

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Price per night from

$241

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

Match: Wheelchair accessible

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Price per night from

$258

*** Isla Del Sol Paradise ***

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$172

Family friendly condo on the beach - Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$156

Beach Front Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$446

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$342

Peace and Quiet in Gated Community on Boca Ciega Bay

Gulfport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$77

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$297

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$308

2 Bedroom Condo Newly Renovated Excellent Location!

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$249

Riverfront Tropical Paradise W/ Private Island-Newly Updated Listing

Braden River house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$251

Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$429

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Wheelchair accessible

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Price per night from

$172

Outdoor Oasis Awaits! Your perfect vacation spot just steps away from the beach

Anna Maria Island house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Wheelchair accessible

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Price per night from

$1,018

Gulfport Waterfront Mid-Century Modern Masterpiece

Gulfport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$366

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wheelchair accessible

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Price per night from

$201

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

Match: Wheelchair accessible

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Price per night from

$117

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