Vacation Rentals & Beach Rentals in Siesta Key

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1,818 beach rentals

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: Shared outdoor pool (heated) Wheelchair adapted

All filters match

Price per night from

$286

Marriott Grande Vista Resort and SPA

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated) Wheelchair adapted

All filters match

Price per night from

$295

Christmas Week Condo/ Next to Disney/ Dates Flexible/ River Island location

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated) Wheelchair adapted

All filters match

Price per night from

$196

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WESTGATE LAKES RESORT & SPA-Orlando Studio

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 55 minutes

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

1 of 2 filters match

Price per night from

$129

villanirvana

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Family trip” This was a wonderful trip and the house was magnificent. My family felt very at home and the pool was wonderful after a long hot day at the park.

Responds fast! avg. 3 hours 6 minutes

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

1 of 2 filters match

Price per night from

$173

Vanderbilt Beach

Naples house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 33 minutes

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

1 of 2 filters match

Price per night from

$74

My Orlando home

Celebration apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$180

Executive Bay Club- great unit, great location!,

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

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

1 of 2 filters match

Price per night from

$205

Royal Harbor - downtown Naples condo

Naples condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$249

Fort Myers, Lake View, 2Br $ 2BA, Best Beaches

Iona apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$81

Welcome to our charming and stylish home located at Windsor at westside

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

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

1 of 2 filters match

Price per night from

$401

Modern, chic & cozy 2br 2ba apartment in Wynwood

Miami apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$184

COURTYARD VIEW modern condo near Gulf of Mexico beaches

Clearwater house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

1 of 2 filters match

Price per night from

$172

COZY RETREAT modern condo near Gulf of Mexico beaches

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Fabulous!” Owner was great! Condo is everything you need or want. Every detail is perfect. Pool was just steps away.

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

1 of 2 filters match

Price per night from

$161

Bonita Isles spectacular Hidden Gem in the heart of Bonita Springs/Naples Fl.

Bonita Springs villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$115

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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

1 of 2 filters match

Price per night from

$573

Howell's Nest at Windsor Hills

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$171

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

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$103

Treviso Bay - Luxury Resort Style Golf Community

Naples apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$252

Beautiful Lakeview Condo at Falling Waters (Davis Blvd) in Naples Florida

Naples apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 57 minutes

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

1 of 2 filters match

Price per night from

$175

The Vue at Downtown Orlando

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$138

Gorgeous Water View, Condo!Completely Renovated 2015,Wifi

Tierra Verde condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$201

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$377

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

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$430

Spacious 2nd floor coach home!

Naples condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$229

Beautiful Secluded Island Home, Great Fishing

Everglades City house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$172

Sunny Side Pavilion at the Avalon

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

1 of 2 filters match

Price per night from

$95

Friends and Family close to beaches and more

Fort Myers house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$126

Beachfront Condo With Weekly Rentals

Fort Myers Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Estero Sands was PERFECT!!” Estero Sands was a great place for our family! We've stayed in Ft. Myers many times and this stay was one of the best. The owners that were on site were very nice. The grounds were very well kept. Literally steps to the beach!!! Loved it!!

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

1 of 2 filters match

Price per night from

$327

Guava Getaway - Relax, Renew, and Rejuvenate

Lakewood Ranch condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$171

NEW LISTING! WONDERFUL AND MODERN CONDO WITH POOL VIEW

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 32 minutes

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

1 of 2 filters match

Price per night from

$227

Madeira Bay Enjoy Sunrise Views from Balcony Overlooking Intracoastal Waterway

Madeira Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

1 of 2 filters match

Price per night from

$229

Waterfront Condo

Vero Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$81

☀Across from Resident's Beach☀2/2 Marco Condo☀

Marco Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

1 of 2 filters match

Price per night from

$84

Clearwater Beach Condo 3BR fits 6-10 ppl

Clearwater condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 28 minutes

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

1 of 2 filters match

Price per night from

$229

1 bedroom single story ocean view

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

1 of 2 filters match

Price per night from

$360

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: Wheelchair adapted, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$137

2 bedroom Florida condo unit 13 at family friendly resort

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

1 of 2 filters match

Price per night from

$425

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rentals in Siesta Key

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