Houses Longboat Key

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514 houses

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

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Stereo system

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Price per night from

$344

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Shared outdoor pool (heated) Stereo system

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Price per night from

$286

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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

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

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Price per night from

$95

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Stereo system, Rental types, Shared outdoor pool (heated)

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Price per night from

$338

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

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Price per night from

$409

Amazing Village Cottage! Walk to Whitney Beach!

Longboat Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Stereo system, Rental types, Shared outdoor pool (heated)

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Price per night from

$393

Private Retreat on Siesta Dr

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 49 minutes

2 of 3 match: Stereo system, Rental types, Shared outdoor pool (heated)

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Price per night from

$515

St Armand's Private Home on Jackson Drive

Lido Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Stereo system, Rental types, Shared outdoor pool (heated)

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Price per night from

$381

"Lido Lookout" Beach Paradise Private Home on Lido Key

Lido Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

2 of 3 match: Stereo system, Rental types, Shared outdoor pool (heated)

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Price per night from

$2,971

Limefish

Holmes Beach house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Stereo system, Rental types, Shared outdoor pool (heated)

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Price per night from

$2,057

Beach Bliss

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

2 of 3 match: Stereo system, Rental types, Shared outdoor pool (heated)

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Price per night from

$1,143

Bird of Paradise at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

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Price per night from

$489

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

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Price per night from

$337

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

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Price per night from

$310

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

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Price per night from

$258

Luxurious 2 BR Condo-Short Walk to Siesta Beach/1 Small Dog (25 lbs Max) Allowed

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“a fine 2 weeks in Siesta” charming property, that was comfortable for four. The unit was very clean and fresh upon arrival. The neighbours were friendly and the overall property well kept. Siesta Key is a quiet community with usual shopping amenities over the causeway. This property was a brief 10 minute walk to the beach. Would we stay again, yes.

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

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Price per night from

$165

Gulf Beach Place, miles of whites sandy beach

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$287

Blue Bayou

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Home away From Home” I've been staying at the Graham's condo once or twice a year for the last 9 years or more. It's always been pristine clean. Accomodations are the best. Rooms large and bright and fully equipped. Decor is so welcoming. Location is the best. Only decisions to make are beach or pool, and where to eat tonight! I consider it my "home away from home." You won't be disappointed, and the value cannot be beat. Don't hesitate to book your reservation.

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

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Price per night from

$172

Cathy's Crescent Condos-Siesta Key, FL GULF FRONT

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great View” We stayed at Kathy’s condo during the 4th of July week. The Condo was great and the view was amazing. We enjoyed the fireworks display and easy access to the beach. We look forward to renting her condo again in the future.

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

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Price per night from

$314

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

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Price per night from

$271

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

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Price per night from

$101

Charming Siesta Key Village Unbeatable Location

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

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Price per night from

$189

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$144

“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!!

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$144

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$161

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$343

Zilli Ocean Front 101

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$286

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$297

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$308

Island Village Hideaway! Steps to Sand

Longboat Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Shared outdoor pool (heated), Rental types, Stereo system

2 of 3 filters match

Price per night from

$193

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Stereo system, Rental types, Shared outdoor pool (heated)

2 of 3 filters match

Price per night from

$46

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

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$153

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!

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$453

Anna Maria The Pink Flamingo

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 41 minutes

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$458

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$205

Sandy Toes Town Home

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$272

Siesta Key private beach access

Siesta Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

2 of 3 match: Rental types, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$509

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, Shared outdoor pool (heated), Stereo system

2 of 3 filters match

Price per night from

$189

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