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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) Kettle

All filters match

Price per night from

$343

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Rental types Shared outdoor pool (heated) Kettle

All filters match

Price per night from

$286

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Kettle

All filters match

Price per night from

$276

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Shared outdoor pool (heated) Kettle

All filters match

Price per night from

$284

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Rental types Shared outdoor pool (heated) Kettle

All filters match

Price per night from

$172

Tropical Breeze Triple Cottages, Sleeps 16

Sarasota house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

Match: Rental types Shared outdoor pool (heated) Kettle

All filters match

Price per night from

$679

Sea Glass Dual Cottages, Sleeps 12, Heated Pool

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Rental types Shared outdoor pool (heated) Kettle

All filters match

Price per night from

$400

Flamingo Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Kettle

All filters match

Price per night from

$172

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Shared outdoor pool (heated) Kettle

All filters match

Price per night from

$172

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

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

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$337

"Lido Lookout" Beach Paradise Private Home on Lido Key

Lido Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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

2 of 3 filters match

Price per night from

$2,966

Private Retreat on Siesta Dr

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 49 minutes

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

2 of 3 filters match

Price per night from

$514

St Armand's Private Home on Jackson Drive

Lido Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$380

Limefish

Holmes Beach house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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

2 of 3 filters match

Price per night from

$2,054

Amazing Village Cottage! Walk to Whitney Beach!

Longboat Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$392

Beach Bliss

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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

2 of 3 filters match

Price per night from

$1,141

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

2 of 3 filters match

Price per night from

$46

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), Kettle

2 of 3 filters match

Price per night from

$336

Lifestyle on the island

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 3 filters match

Price per night from

$172

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), Kettle

2 of 3 filters match

Price per night from

$165

Crystal Sands Unit 308 Siesta Key, Florida

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Vacation Rental” We have been coming to Siesta Key for our Vacations for years... We have stayed at a number of Units at Crystal Sands, Crescent arms and El Presidente... Crystal Sands Unit 308 is one of the best Units we have stayed at... It has a great view of the Beach and Pool... You can watch the Sunsets and Moonsets right from the Lanai... The Unit is Roomy, Clean and had all the appliances, Dishes and Linens we needed... The Washer\Dryer in the Unit is very convenient... It has a New 60" Hdtv in the Living Room with an incredible picture... Jim left printed instructions for the Hdtv, Washer and Dryer which made it very easy to use the appliances in the Unit... We are looking forward to staying in Crystal Sands Unit 308 again for our next trip to Siesta Key...

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

2 of 3 filters match

Price per night from

$428

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

2 of 3 filters match

Price per night from

$143

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

2 of 3 filters match

Price per night from

$283

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), Kettle

2 of 3 filters match

Price per night from

$160

Zilli Ocean Front 101

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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

2 of 3 filters match

Price per night from

$284

BEAUTY ON THE BEACH! Crescent Arms 601S FULL FRONT VIEW

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$313

Zilli Ocean Front 201 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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

2 of 3 filters match

Price per night from

$296

“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), Kettle

2 of 3 filters match

Price per night from

$143

Sea~N~Blue

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 3 filters match

Price per night from

$400

Amazing beachfront View & balcony on Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$433

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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

2 of 3 filters match

Price per night from

$307

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), Kettle

2 of 3 filters match

Price per night from

$172

GULF COAST DESTINATION

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$200

Crescent Beach resort, Heated Pool, Jacuzzi, Tennis, Barbeques

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

2 of 3 filters match

Price per night from

$314

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

2 of 3 filters match

Price per night from

$192

Waterview Oasis Retreat, minutes to Anna Maria Island and IMG

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 3 filters match

Price per night from

$109

Zilli Tower 503

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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

2 of 3 filters match

Price per night from

$343

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

2 of 3 filters match

Price per night from

$430

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rentals in Longboat Key

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