Houses Longboat Key

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Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Staffed property Smoking allowed

All filters match

Price per night from

$149

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The Hideaway: 4/2 W Heated Pool and Outdoor Spaces, 10 mins to Sarasota Beach

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

2 of 3 match: Staffed property, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$373

2 of 3 match: Staffed property, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$316

Delightful Oasis #2

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Staffed property, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$178

2 of 3 match: Staffed property, Rental types, Smoking allowed

2 of 3 filters match

Price per night from

$172

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Smoking allowed, Rental types, Staffed property

2 of 3 filters match

Price per night from

$345

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

2 of 3 match: Smoking allowed, Rental types, Staffed property

2 of 3 filters match

Price per night from

$2,289

Firethorn 830 at Midnight Cove Siesta Key

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Smoking allowed, Rental types, Staffed property

2 of 3 filters match

Price per night from

$142

Chinaberry 924 at Midnight Cove Siesta Key, FL.

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Smoking allowed, Rental types, Staffed property

2 of 3 filters match

Price per night from

$171

Doveplum 221 at Midnight Cove Siesta Key, FL.

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Smoking allowed, Rental types, Staffed property

2 of 3 filters match

Price per night from

$256

Shorewalk waterfront Condo Bradenton

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Nice and affordable condo convenient to shopping and restaurants.” This unit has been updated and is a very comfortable place to stay. The owner responded promptly when we contacted him.

Responds fast! avg. 2 hours 1 minutes

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$96

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 46 minutes

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$194

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$448

🏝Paradise on the Sarasota Bay, Close to Gulf Beaches🏝 (Sarasota)

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$194

Sarasota Waterfront and Marina Community with Tikki Bar and Grill

North Sarasota condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$102

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$424

Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$290

Blue Heron Inn: 1/1 Spacious Apartment, 15 mins to beaches, pet friendly

Oneco apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Rental types, Staffed property, Smoking allowed

1 of 3 filters match

Price per night from

$127

Lady Palm Apt: 1/1 with 2 beds, garden vibes and outdoor spaces! Pet friendly

Bradenton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Rental types, Staffed property, Smoking allowed

1 of 3 filters match

Price per night from

$144

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$410

Sunsets on Beach Siesta Key top floor #402

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$230

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$240

~ SUPER SPECIAL from $99/night ~ OCEAN FRONT DLX STUDIO

Longboat Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 56 minutes

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$194

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$482

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$286

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$234

House of Blues - Lovely 2-Bedroom Condo with Pool, W&D and Patio

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Staffed property, Smoking allowed

1 of 3 filters match

Price per night from

$201

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$272

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$431

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$144

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$338

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$437

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

Siesta Key condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$905

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$298

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$309

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$285

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$344

1 of 3 match: Rental types, Smoking allowed, Staffed property

1 of 3 filters match

Price per night from

$144

Viewing 38 of 535
rentals in Longboat Key

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