Vacation Rentals & Beach Rentals in Siesta Key

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764 beach rentals

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 1 minutes

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Price per night from

$266

Beachfront Getaway in Siesta Key

Siesta Key townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Very comfortable, nice amenities and well run.” Loved the beach and the nearby restaurants. The free trolly ride was easy to use and a great way to go into the village.

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$224

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

Walk to Beaches, Bay Complex, Heated Pool,1st Flr

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$138

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

Responds fast! avg. 4 minutes

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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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$163

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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$305

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

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$133

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 23 minutes

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Price per night from

$390

Beautifully Renovated & Modern in Harbor Towers

Siesta Key apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$206

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

$315

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

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$213

Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“What a great view” We usually rent a house one block from the main Siesta Key beach area. This year friends rented the house and my husband and I stayed in this condo for a week. Loved the view of the beach from the living room! Loved the lani! Location was great. Pool was massive compared to our usual house pool, however we did have to walk thru parking lot to get there. The noise from the hall was annoying. And I did miss my temperpedic mattress, but had a great relaxing time.

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$328

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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$189

Beachfront, Private Beach, Full Ocean Views, Pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$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

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Price per night from

$332

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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$115

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

$182

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

$172

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

$165

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

$205

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

$687

Living the Dream - Mermaid: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$343

Big Pass Hideaway

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$161

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$999

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$409

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$109

Full Ocean Views w/Private Beach on Siesta Key!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 4 minutes

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Price per night from

$288

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$344

AUGUST SPECIAL! 2 min. drive to Siesta Key! Very Clean!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Wonderful Place to stay” Confortable, and quick easy drive to good restaurants and most important The Beach! Although it rained the whole weekend, we were close to our family for the birthday and bridal shower celebration.

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Price per night from

$212

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