Vacation Rentals & Beach Rentals in Anna Maria Island

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194 beach rentals

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared indoor pool Sea view

All filters match

Price per night from

$115

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared indoor pool Sea view

All filters match

Price per night from

$173

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ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$161

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$173

LaPlaya 206C-Gorgeous vistas of the Gulf

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$414

LaPlaya 104A- Gulf front! Walk right from your lanai onto the private beach.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$311

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$414

LaPlaya 204D-Beach-lovers paradise! 200 feet of private beach

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$414

LaPlaya 101E-Relax on your private lanai under the palms!

Longboat Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$275

LaPlaya 205D-Spectacular sunsets from your private Gulf-front lanai or sundeck.

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$414

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$414

LaPlaya 106A-Beach front! Steps to the white sand and turquoise Gulf of Mexico.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$376

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$220

LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$339

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$376

LaPlaya 107A-Soak up the sun or float in the warm Gulf waters.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Sea view, Shared indoor pool

1 of 2 filters match

Price per night from

$311

Beach Dreams "Tangerine Dreams Villa "

Bradenton Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$344

Beach Dreams "DreamBoat Villa"

Bradenton Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$487

Tiny Home Camping Experience

St. Petersburg yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$287

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: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$222

Sunset Beach One Bedroom Gulf View

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$230

Flamingo Love Apartment by the beach

Treasure Island house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$183

St Pete Beach fun in sun!

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$155

Direct Beachfront Unobstructed Ocean View Feet on White Sand Condo With Pool

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$345

Sunshine Paradise at Redington Beach

Redington Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$229

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 23 minutes

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$390

Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Sea view

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: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$659

3 min Walk to Beach! Studio Condo, Hidden Jewel!

St. Pete Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$207

Gulf Beach Unit 03 on Beach side, gorgeous interior, miles of beach, Anna Maria

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$401

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$301

Redington Towers 1 Beachfront 2 Bedroom Condo

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$218

Beach Front Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$448

NEW! Luxurious Coastal Condo 5 minutes to Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$402

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$230

7 mins From the beach and 15 mins Maximo Boat Ramp

Kenneth City house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$300

Steps to the Beach

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$164

Caddy Cottage- On Sunset Beach

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Shared indoor pool, Sea view

1 of 2 filters match

Price per night from

$217

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rentals in Anna Maria Island

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