Vacation Rentals & Beach Rentals in Anna Maria Island

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311 beach rentals

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared indoor pool Water sports

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Price per night from

$173

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Palm Haven on Treasure Island 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, Water sports

1 of 2 filters match

Price per night from

$183

St. Pete Beach Bungalow 5 minutes from Downtown!

St. Petersburg house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$183

Castnetter Beach Resort 6

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$316

Tiny Home Camping Experience

St. Petersburg yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$287

Turtle Heaven apartment by the beach

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$183

Dolphin Pod Apartment by the beach

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$183

St Pete Sunshine Cottage *ENTIRE HOME*

St. Petersburg house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$171

Artist Housing Near Downtown - Townhouse 4

Sarasota townhouse

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$144

Artist Housing Near Downtown - Townhouse 3

Sarasota townhouse

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$144

Artist Housing Near Downtown - Townhouse 2

Sarasota townhouse

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$144

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$458

Castnetter Beach Resort 2

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$316

Castnetter Beach Resort 5

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$316

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Water sports, 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: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$173

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: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$311

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: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$340

1 of 2 match: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$377

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: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$311

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

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$415

LaPlaya 206C-Gorgeous vistas of the Gulf

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$415

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: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$377

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: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$415

1 of 2 match: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$221

1 of 2 match: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$415

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

Longboat Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$276

1 of 2 match: Water sports, Shared indoor pool

1 of 2 filters match

Price per night from

$415

Boca Ciega Condo, #408, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$201

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$345

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$218

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$502

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: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$207

Crystal Sands Unit 308 Siesta Key, Florida

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Vacation Rental” We have been coming to Siesta Key for our Vacations for years... We have stayed at a number of Units at Crystal Sands, Crescent arms and El Presidente... Crystal Sands Unit 308 is one of the best Units we have stayed at... It has a great view of the Beach and Pool... You can watch the Sunsets and Moonsets right from the Lanai... The Unit is Roomy, Clean and had all the appliances, Dishes and Linens we needed... The Washer\Dryer in the Unit is very convenient... It has a New 60" Hdtv in the Living Room with an incredible picture... Jim left printed instructions for the Hdtv, Washer and Dryer which made it very easy to use the appliances in the Unit... We are looking forward to staying in Crystal Sands Unit 308 again for our next trip to Siesta Key...

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$431

1 Bedroom Madeira Beach Cottage

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$155

Redington Towers 1 Beachfront 2 Bedroom Condo

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$218

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$333

Beach Front Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Water sports

1 of 2 filters match

Price per night from

$448

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