Vacation Rentals & Beach Rentals in Anna Maria Island

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294 beach rentals

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Trampoline

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Price per night from

$172

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2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$571

Gorgeous Water View, Condo!Completely Renovated 2015,Wifi

Tierra Verde condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$200

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

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$428

Oceanfront? You bet! A Must See!

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$243

1 bedroom single story condo near pool

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$294

2 bedroom poolside condo steps from ocean beach and dock on bay

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$424

1 bedroom single story ocean view

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$359

Nice St Pete Beach Condo steps from beach and near restaurants

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$136

2 bedroom Florida condo unit 13 at family friendly resort

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$424

Kima 204 Direct Gulf Front in Madeira Beach

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$286

Madeira Bay Enjoy Sunrise Views from Balcony Overlooking Intracoastal Waterway

Madeira Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$229

Beautiful Beach Front Condo with direct view of the Gulf of Mexico

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$286

Kima 102 2bed/2bath Gulf Front Condo in Madeira Beach READY TO ENJOY!!

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$286

Kima 403 2bedroom Gulf Front Condo PRICELESS SUNSETS!

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$221

Kima 205 Spacious 2bd/2bath Madeira Beach Gulf Front Condo Endless Views

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$286

Gulf Front Beauty, 30 Day Minimum

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 5 minutes

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$191

escape to paradise

Madeira Beach apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$206

“Great stay in Sarasota” My husband and our two daughters spent a wonderful four days in Sarasota. The townhome we stayed in was beautiful and had all the amenities we needed. We spent every day at the beach and relaxed at the townhome in the evenings. We would definitely stay here again and have recommended this place to our family and friends. Thanks Louie!

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$433

Siesta Key Gulf View Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 33 minutes

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$445

231A Madeira Beach Yacht Club

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$148

Luxury Waterfront Views/Pool/1400sf/2 min to Beach

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 32 minutes

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$338

Siesta Key vaca rental

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$229

Welcome to Paradise-6 miles from Anna Maria Island Beaches

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$205

A Taste of Paradise - tnzwaterside

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$314

Luxury Apartment, 90 Steps from the Ocean

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$186

AMI Beach Front Condo - heated pool and less than 50 steps to the Beach!

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$343

Frangi Pani at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$488

Beachplace Building 7 Great View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$180

Best of both worlds! Fish in bay or go to beach!

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Modern place in an awesome location” My family really enjoyed our time at this place. It was very clean, a convenient end unit, and close to the beautiful beach. Having the Intracoastal and pool was great, too. Being fully stocked and 2 TVs was a welcome surprise. Thanks for a great stay!

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$227

Walk to Beach, private condo with pool

Holmes Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$257

4 minute flip flop walk to the beach! Starfish 2/2

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$337

Siesta Key/Derby Bay

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect!” Our family really enjoyed staying here! The villa was very well maintained and cleaned. It was stocked with everything you would need. The owner was very responsive to any concerns. We had a super nice neighbor and my boys loved fishing off the dock. I would recommend renting a golf cart to go to the beach if you have children (with toys etc) or elderly people with walking concerns. It is quite a walk to get to the beach (because you also have to walk down to the cross walk then across the street). The beach in front of the Aloha Kai property is very wide (great because it was never crowded like in front of other resorts) but it was an even farther walk to the water. We have always stayed beach front but needed more rooms than were available in my booking time frame this year. This property has changed the way I will book on siesta in the future. My boys LOVED fishing everyday off the dock. They caught lots of cool fish right off the back. The street that this villa is on was very quiet for our stay. Everyone was very kind & the property is very beautiful! We hope to come back very soon! It was a wonderful experience.

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$286

Gorgeous Beach View Condo

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$189

Ten35 Seaside - Direct Gulf View: Residence 601

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$923

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$177

Beach Vacation rental

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$246

Come join us for your Winter Migration!!!!!!!!!!

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Trampoline, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$103

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rentals in Anna Maria Island

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