Houses Longboat Key

Updating...

age 0-16
643 Results

Relevance

Price: low to high

Price: high to low

Reviews

643 houses

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Bicycles available Staffed property Golf course on site or within 15 min walk

All filters match

Price per night from

$149

These homes match some but not all of your filters. Clear all filters

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Bicycles available

3 of 4 filters match

Price per night from

$630

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

3 of 4 filters match

Price per night from

$435

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

3 of 4 filters match

Price per night from

$114

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.

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

3 of 4 filters match

Price per night from

$115

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

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

3 of 4 filters match

Price per night from

$744

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

3 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

3 of 4 filters match

Price per night from

$117

Responds fast! avg. 0 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Bicycles available

3 of 4 filters match

Price per night from

$229

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Bicycles available

3 of 4 filters match

Price per night from

$108

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Bicycles available

3 of 4 filters match

Price per night from

$515

Anna Maria Island/ IMG Academy/ Beach/ HotTub/ Bikes/ Kayaks/ Golf/ Fishing

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Bicycles available

3 of 4 filters match

Price per night from

$286

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

3 of 4 match: Staffed property, Rental types, Golf course on site or within 15 min walk, Bicycles available

3 of 4 filters match

Price per night from

$476

Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Bicycles available

2 of 4 filters match

Price per night from

$191

Anna Maria Island Sunshine Kiss Villa

Holmes Beach studio

  • Studio
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Bicycles available

2 of 4 filters match

Price per night from

$151

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

2 of 4 match: Rental types, Bicycles available, Golf course on site or within 15 min walk, Staffed property

2 of 4 filters match

Price per night from

$177

Rambo's Beach Retreat! Tradewinds Unit 14

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Rental types, Staffed property, Golf course on site or within 15 min walk, Bicycles available

2 of 4 filters match

Price per night from

$452

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

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$194

2 of 4 match: Rental types, Bicycles available, Golf course on site or within 15 min walk, Staffed property

2 of 4 filters match

Price per night from

$284

2 of 4 match: Bicycles available, Staffed property, Rental types, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$286

Mid Century Home With Private Heated Pool

Tallevast house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Bicycles available, Staffed property, Rental types, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$182

Stunning & Bright Sarasota Home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Bicycles available, Staffed property, Rental types, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$395

Banana Cabana: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$239

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$285

Responds fast! avg. 11 minutes

2 of 4 match: Rental types, Bicycles available, Golf course on site or within 15 min walk, Staffed property

2 of 4 filters match

Price per night from

$132

Anna Maria Island Beach Watch

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Bicycles available, Staffed property, Rental types, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$249

Anna Maria Island Beach Happy-Direct Beach Front-1BR-1BR

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

2 of 4 match: Bicycles available, Staffed property, Rental types, Golf course on site or within 15 min walk

2 of 4 filters match

Price per night from

$228

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$178

Crescent Beach Villas - La Estrella: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$273

Ten35 Seaside - North Water View: Residence 606

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$776

Crescent Beach Villas - La Perlita: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$273

Ten35 Seaside - Island View: Residence 406

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$559

Ten35 Seaside - Direct Gulf View: Residence 301

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$856

Ten35 Seaside - Island View: Residence 408

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$548

Ten35 Seaside - North Water View: Residence 506

Siesta Key condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$776

BEACH RESIDENCES on Siesta, aka The Hyatt – 3 Bed/3 Bath Luxury Penthouse

Siesta Key hotel apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$513

Ten35 Seaside - Island View: Residence 404

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$548

Ten35 Seaside - South Water View: Residence 302

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$605

Jamaica Royale - Beachfront Tower: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Rental types, Golf course on site or within 15 min walk, Bicycles available, Staffed property

2 of 4 filters match

Price per night from

$376

Viewing 38 of 643
rentals in Longboat Key

×

Also consider