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Vacation Rentals & Beach Rentals in Siesta Key

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388 beach rentals

Siesta Key Villa A - Only 150 yards to Crescent Beach and heated pool!

Siesta Key villa

2 bedrooms / 1 bathroom / sleeps 4

“This place was absolutely perfect!” This place was amazing. We stayed here just a week:( but we will definitely be back. The condo was clean, fully equipped, comfortable and perfectly located. The beautiful beach was a very short walk away and the lovely heated pool was even closer. I came here with 2 of my daughters 18 and 22. They loved it also. The restaurant “ The Toastd Mango” right across the street had delicious omelettes and friendly staff. The trolley stop is also right across the street and it takes you into the village. And back free! So park your car because everything is right here:) ENJOY

Responds fast! avg. 1 hour 23 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$149

WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 4

“Absolutely Wonderful” We stayed the second week of September at Bay Oaks Condos, and it was absolutely WONDERFUL! We basically had the run of the condo to ourselves, including the swimming pool, which was the only place my toddler wanted to hang out. It's located right in the middle of the island so it was only a short drive to amazing restaurants and the beautiful Siesta Beach. The condo itself was lovely, modernly updated and had everything we needed to make it our home away from home. My toddler constantly asks when we'll go back to our "little house", and I am happy to tell him that we will be back next year!

Responds fast! avg. 2 hours 16 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$141

Remodeled 2br 2ba with private patio, beautiful water views, walk to #1 beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 11 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$107

Jamaica Royale #92 on the #1 Beach in the USA!

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$289

Top Floor End Unit Directly Across the Street from Siesta Key public beach

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

“Awesome Condo Unit” There were 4 in our party and nothing that we were disappointed with. We absolutely loved every moment!! We will definitely rent this unit again!!

Match: Shared outdoor pool (heated)

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$146

WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful and memorable vacation with our son,wife and grandchil” My husband and I rented unit B41,it was beautifull, tastefully decorated stainless steel appliances and new furniture. The owners thought of everything.Very pleased to have a washer and dryer in unit. The layout of this rental was spacious,the bed was very comfortable I slept like a baby which is rare when I'm away from home.The view of the intercostal water way and tropical landscaping were breathtaking whether relaxing in living room or dinning.It was very peaceful ,walking distance to Siesta keys famous beach and close to all amenities. Would recommend Bay Oaks!Thanks Barbara Okin.

Responds fast! avg. 2 hours 24 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$163

Gorgeous Direct gulf Front 2 Bedroom Condo on Siesta Keys... JUST REMODELLED

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$188

Siesta Key Villa B - Only 150 yds. to Crescent Beach and heated pool!

Siesta Key villa

2 bedrooms / 1 bathroom / sleeps 4

“Another great stay!” Location is great and owners are awesome to work with! Clean and fully furnished! Thanks for another great stay Derek and Marina! Look forward to next time!

Responds fast! avg. 1 hour 23 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$149

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 39 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$276

The Perfect 2Bedroom/2Bath Steps Away From Siesta Key Beach- BiancoSands

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$239

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.

Responds fast! avg. 1 hour 22 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$214

3 Bedroom/ 2 Bath unit across from Siesta Key Beach Access.- Islamorada

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 8

Match: Shared outdoor pool (heated)

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Price per night from

$206

Luxury Villa, Sleeps 6 Comfortably Located on Siesta Key Beach, Sarasota Florida

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 8 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$205

Jamaica Royale #100-Peaceful Gulf Side Condo

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

“Spring break” This unit was beautifully done; recently renovated, impeccably clean and very close to the beach! The owner was e trendy helpful and accommodating. She made it easy and if you are headed to Siesta Key, you must stay here!

Responds fast! avg. 1 hour 55 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$197

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.

Responds fast! avg. 1 hour 29 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$160

Charming Siesta Key Condo, Walk to Beach, Pool

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 1 hour 44 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$117

Best Deals on Siesta Key

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

“Nice and easy to get around” You have a wonderful neighbor. I was able to access all the amenities you described. Navigated through out the area with ease.

Match: Shared outdoor pool (heated)

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Price per night from

$103

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 9 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$213

Beachfront- Gulf View! 2 BR/BA Crescent Arms 603S, #1 Beach in the US.

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 36 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$179

Luxurious 2 BR Condo - Short Walk to Siesta Beach

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.

Match: Shared outdoor pool (heated)

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Price per night from

$141

Luxury Condo Ground Floor Across the Street

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$176

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

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

“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.

Responds fast! avg. 3 hours 27 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$220

Beach Walk Townhouse

Siesta Key townhouse

3 bedrooms / 3 bathrooms / sleeps 6

“Great vacation and Great Accomations” We loved the accommodations. Great location close to beach access and to the village.The pool was wonderful with lovely landscaping. The house was spacious and very clean. Virginia the manager was also great! We would definitely stay here again.

Responds fast! avg. 42 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$251

Siesta Key 2 BR, 2 1/2 Bath - *Across From Beach - Pool-view* - Newly Renovated

Siesta Key apartment

2 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 28 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$227

# 1 beach in USA SIESTA KEY Gulf side 2 Bed 2 Bath at Jamaica Royale #104!

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 47 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$200

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 5

Match: Shared outdoor pool (heated)

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Price per night from

$117

"Safe & Clean" -Honeymoon Suite - Gulf views - next to Siesta Key Beach

Siesta Key apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 50 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$194

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♡

Responds fast! avg. 1 hour 45 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$185

Siesta Key, Heated pool, Gulf and Bay, Cute Siesta Key Condo, Gated

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 10 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$125

Siesta Key Condo, Crescent Arms, unit 605 South

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 20 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$221

Siesta Key - #1 Beach in USA

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$143

WOW Factor Siesta Key Beach Gulf Front Condo in Siesta Dunes on #1 Beach in USA

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 19 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$277

Crescent Arms 703S, Beachfront Penthouse, Gulf View from Every Room! 2BR-BA

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 5

“vacation excellence” Room is great. View is outstanding. We really enjoyed our stay. Room is quiet no outside noise. We recommend

Responds fast! avg. 36 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$182

Siesta Villa Whispering Palms

Siesta Key villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 55 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$188

Renovated 2 bedroom with beach views and pool access!!-Living the Dream, Mermaid

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$216

Crystal Sands Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Shared outdoor pool (heated)

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Price per night from

$405

Siesta Key Condo w/Balcony - Walk to Beach and Bay

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$137

Siesta Key Vacation Townhouse directly across the street from #1 Beach in the US

Siesta Key townhouse

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 51 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$234

Viewing 38 of 388
rentals in Siesta Key

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