Houses Longboat Key

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1,017 houses

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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$149

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Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$234

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$240

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$286

Private Beach Access - Home away from Home - 2 BR 2 BA - Furnished Condo

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$178

Ten35 Seaside - Island View: Residence 404

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$548

Ten35 Seaside - Island View: Residence 604

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$559

Ten35 Seaside - Direct Gulf View: Residence 501

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$947

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$337

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

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$209

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$430

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$284

Gulf Holiday: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$171

Living the Dream - Starfish: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$343

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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$343

Lido Beach Villa, 1.2k sf, 1 block to the beach

Lido Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$184

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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$308

Beach to Bay Tropical Oasis! 2Bed/2Bath Longboat Key Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$153

2 Bedroom, 2 Bathroom condo / Heated pool / 7 minute walk to beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$177

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!

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$453

4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

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$514

Siesta Key Townhouse across from Pristine Sands of Siesta Key 2B/2B sleeps 6

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic week in Siesta Key” The townhouse was fantastic and fully equipped with everything we needed for a very comfortable week. The location was outstanding - right across from the beach and the free trolley to the Village stopped right outside. The garage had everything the family needed to take to the beach and we met some lovely people around the pool. Thank you Michelle for your hospitality - we hope to be back soon.

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$189

Responds fast! avg. 11 minutes

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$132

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

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$117

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$622

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

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$115

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$192

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$745

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

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$114

Firethorn 830 at Midnight Cove Siesta Key

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$142

Chinaberry 924 at Midnight Cove Siesta Key, FL.

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$171

Doveplum 221 at Midnight Cove Siesta Key, FL.

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$256

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$344

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

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$2,284

120 Steps to the Beach with beach gear included!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$423

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

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Price per night from

$95

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

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$447

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

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$194

Viewing 38 of 1,017
rentals in Longboat Key

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