Vacation Rentals & Apartments in Longboat Key

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1,353 apartments

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: Swimming pool Wheelchair adapted

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Price per night from

$286

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BeachLife

Indian Shores apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$182

Take a step closer to paradise! SEAGATE – Apt. 302

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Would love to return several times a year....near perfect!” The condo was beautiful, well appointed and maintained. Located on a nearly perfect beach. It appears we were the first tenants after hurricane Irma. My only complaint was the AC didn't work for the 1st half. The property manager seemed to be doing all she could to remedy the situation My only recommendation is that maintenance should probably have checked it out along with everything else after the storm. I would still highly recommend this to anyone wanting to experience a beach vacation in a great location and in a wonderful condo. The owner is great to work with also.

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$344

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$573

Gorgeous Water View, Condo!Completely Renovated 2015,Wifi

Tierra Verde condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$201

Kima 204 Direct Gulf Front in Madeira Beach

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$287

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: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$287

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: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$287

Kima 403 2bedroom Gulf Front Condo PRICELESS SUNSETS!

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$221

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: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$287

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: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$192

escape to paradise

Madeira Beach apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Wheelchair adapted, Swimming pool

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: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$434

1 bedroom single story condo near pool

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$295

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: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$425

1 bedroom single story ocean view

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$360

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, Swimming pool

1 of 2 filters match

Price per night from

$425

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$338

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, Swimming pool

1 of 2 filters match

Price per night from

$229

Guava Getaway - Relax, Renew, and Rejuvenate

Lakewood Ranch condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$171

Paradise Found

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$252

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: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$447

231A Madeira Beach Yacht Club

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$148

Bright Clean Happy Vacation Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$115

Island Attitude 2/2 beach condo

Manasota Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$315

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: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$339

Siesta Key vaca rental

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$229

Gorgeous 2nd story 2B condo with vaulted ceiling & leather furniture

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$229

The Meadows golf course view villa

North Sarasota villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$122

Welcome to Paradise-6 miles from Anna Maria Island Beaches

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$205

Luxury Apartment, 90 Steps from the Ocean

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$186

A Taste of Paradise - tnzwaterside

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$315

Tortuga Shoals

Tierra Verde townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$413

Beachplace Building 7 Great View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$180

Walk to Beach, private condo with pool

Holmes Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$258

Lakewood National Bundled Golf Home @Lakewood Ranch, FL

Lakewood Ranch house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$201

Frangi Pani at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$489

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: Wheelchair adapted, Swimming pool

1 of 2 filters match

Price per night from

$344

Viewing 38 of 1,353
rentals in Longboat Key

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