Vacation Rentals & Beach Rentals in Anna Maria Island

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50 beach rentals

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ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Table tennis Trampoline

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Price per night from

$172

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Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$489

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$489

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$489

Anna Maria Island/ IMG Academy/ Beach/ HotTub/ Bikes/ Kayaks/ Golf/ Fishing

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Table tennis, Trampoline

1 of 2 filters match

Price per night from

$287

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$229

Super Cute Cottage--Private--Walk/Bike to Beach

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$258

Beachplace Building 3 unit 302

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$187

Orchid at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$489

Split Leaf at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$489

Coconut at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$489

Shorewalk Condo ED near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$401

Beach front condo on Redington Shores

Redington Shores condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$134

Tropical Treasure Villa - Giant spa and steps from the beach!

Redington Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$942

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$182

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$435

Gulf and Bay Club 3bdrm “E” Luxury END CORNER Unit - RIGHT ON BEACH

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$903

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$114

OCEANFRONT VIEW - PRIVACY OVERLOOKING THE GULF OF MEXICO

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$206

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$1,030

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$516

Modern Lakerfront Condo! 2x Pools~WiFi~Lanai. By IMG~Beaches~Restaurants~AMI~SRQ

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 11 minutes

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$138

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$178

Beach Walk: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$515

Florida Palms Heaven 2B Villa, near tennis IMG Academy & beaches

South Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$148

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$489

Waterview Oasis Retreat, minutes to Anna Maria Island and IMG

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$109

A Somewhere is Here - Changes in Latitude: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$457

A Somewhere Is Here - Changes in Attitude: By Beachside Management

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$411

Off the Hook: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$515

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$2,289

Beautiful Island on Boca Ciega Bay & The Beach

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$115

Beachfront Condo Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” We couldn't have a better time. The condo had everything you could possibly need for cooking, or going to the pool and beach. The condo is a 3 minute walk to the beach, and the weather was perfect. Village is a 5 minute drive and the restaurants were perfect for a family. Definitely coming back!

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$453

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$1,260

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$476

“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$245

*** Isla Del Sol Paradise ***

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$172

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

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Table tennis

1 of 2 filters match

Price per night from

$393

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