Vacation Rentals & Beach Rentals in Siesta Key

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675 beach rentals

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$266

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing

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$201

Walk to Crescent Beach, Wifi, Bay Views From Lanai, Heated Pool, YTube TV, On T

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 4 minutes

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Price per night from

$139

Across the street from SK Beach, New Renovations!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$206

SK Beach Across the Street, WiFi, Overlooks Pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

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$131

Last Minute Availability. Private Beach Access, Pool, Amenities, Dock View

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Beautiful condo” Great location with beach access and walking access to great restaurants. Only downside it was listed as 2 bathrooms when there were only 1 and 1/2

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$174

New Owners & Superbly Renovated, Walk to Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 4 minutes

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$161

Crescent Beach Villas - La Estrella: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$274

Mid Century Modern Canal Home, Pool, King Master

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$305

Walk to Siesta Beach, Heated Pool w/BBQ, Parking

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$133

Beautifully Renovated & Modern in Harbor Towers

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 4 minutes

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Price per night from

$206

Chinaberry 436 at Midnight Cove Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$264

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$316

LuLu Kemp Ridley, Walk to Beach, Heated Pool, BBQ

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$213

Buttonwood 462 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$290

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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Price per night from

$190

Beachfront, Private Beach, Full Ocean Views, Pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 4 minutes

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Price per night from

$263

LuLu's Leatherback Walk to Beach/Village, Pool/BBQ

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

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Price per night from

$225

Doveplum 621 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$167

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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Price per night from

$115

Buttonwood 477 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$290

Firethorn 320 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$249

Firethorn 333 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$249

Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$183

Walk to Beach, Fishing Pier, Tennis, W/D in-Unit

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

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Price per night from

$138

Beach Across the Street, Partial Gulf Views, Pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 4 minutes

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Price per night from

$149

Firethorn 513 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$142

Chinaberry 416 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$264

Chinaberry 943 at Midnight Cove Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$171

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♡

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Price per night from

$310

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.

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Price per night from

$166

Firethorn 610 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$142

LuLu’s Green in the Heart of Siesta Key Village

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 4 minutes

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Price per night from

$213

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

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$337

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$206

Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$688

Firethorn 611 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$142

Firethorn 632 at Midnight Cove Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$137

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