Houses Longboat Key

Updating...

age 0-16
374 Results

Relevance

Price: low to high

Price: high to low

Reviews

374 houses

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Cot available Safe

All filters match

Price per night from

$149

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

Beautiful house for rent at siesta key beach with pool, theater and game room

Siesta Key house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 15

Responds fast! avg. 2 hours 0 minutes

2 of 3 match: Safe, Rental types, Cot available

2 of 3 filters match

Price per night from

$2,856

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Cot available, Safe

2 of 3 filters match

Price per night from

$178

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.

2 of 3 match: Rental types, Cot available, Safe

2 of 3 filters match

Price per night from

$190

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.

2 of 3 match: Safe, Rental types, Cot available

2 of 3 filters match

Price per night from

$475

TROPICCAL, 4 min from the beaches! Meticulously cleaned and sanitized!

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

“Lovely home in an awesome location!” Literally a minute's drive from the beach, this very clean and welcoming home is also convenient to great restaurants and shopping opportunities. It really is in a perfect location, especially considering the affordable price. Walking to restaurants and a rental shop is easy thanks to the sidewalk on Cortes. We even enjoyed a morning run to the beach - biking to the beach would also be a great option (3.5 mi one way.) The home might appear small at first, but we fit 6 comfortably, including 4 teenagers! The best part is the lovely décor that greets you after a long day at the beach or running around. Two thumbs up!

Responds fast! avg. 2 hours 33 minutes

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$144

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$259

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$183

Siesta Key Waterfront Estate heated Pool Privacy!

Siesta Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$716

ISLAND TOWNHOUSE - 200 Steps to the BEACH

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 43 minutes

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$207

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$345

Luxury Modern Oasis in Heart of Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$1,032

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$517

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$631

SUNSET VISTA ON LONGBOAT KEY

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Cot available, Safe

1 of 3 filters match

Price per night from

$287

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$172

Flamingo Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$172

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$172

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$345

The Corner Retreat

Bradenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$183

****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$454

Renovated Beach Front 2BR/2BA Condo, Steps to beach, Gulf of Mexico Views

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$277

Luxury Resort Sleeps 26!

Palma Sola house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 26

Responds fast! avg. 3 hours 39 minutes

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$2,289

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$1,947

Buena Vida: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$515

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$344

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$602

Manatee River Cottage in Historic Old Town

Palmetto cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 3 match: Rental types, Safe, Cot available

1 of 3 filters match

Price per night from

$148

Gorgeous views,spectacular home!

Anna Maria house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$631

Newly renovated beach house near AMI free trolley stop with Private pool

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$562

Tropical Breeze Triple Cottages, Sleeps 16

Sarasota house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$683

Sea Glass Dual Cottages, Sleeps 12, Heated Pool

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$402

Great Townhouse Very Close to the Beach, Shops, and Restaurants

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$344

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Location location” Great house convincent , clean , close to everything

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$121

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$744

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

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$287

Aqua Pina: 2 kings, bar area, foosball, sleep 14

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$1,098

2 of 3 match: Cot available, Rental types, Safe

2 of 3 filters match

Price per night from

$457

Viewing 38 of 374
rentals in Longboat Key

×

Also consider