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Vacation Rentals & Beach Rentals in Siesta Key

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873 beach rentals

Siesta Key 2 Bedroom 1 Bath Modern/Contemporary Decor Apartment

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 5

“Amazing!” I stayed here with my husband and we had a great time! We were in Orlando visiting family and we decided to arrange some us time. The condo was excellent and very clean! Kathy and her husband were very informative, respond quickly,and available when we needed them. What was great was that we had all beach items available to us and were very useful. We were in close proximity to everything and the beach and restaurants were great! Everyone in the area was very friendly and my husband and I want to definitely come back!

Responds fast! avg. 1 hour 29 minutes

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$177

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

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$141

Walk to the beach from this adorable condo. Beachside. Perfect location. Bikes,

Siesta Key house

1 bedroom / 1 bathroom / sleeps 2

“Book with Island Time!” We really lucked out with our first Flipkey booking. My husband and I traveled to Siesta Key last year for our honeymoon, and we returned this year to celebrate our anniversary. The property had everything we could possibly have wanted -- a very short and easy walk to beach access 13, Point of Rocks, and many restaurants (aaaaand the liquor store), a very comfortable bed with the appropriate amount of pillows (EIGHT), a fully equipped kitchen with everything we needed to eat in when we wanted, a large covered porch, and everything was CLEAN. Angel was a fantastic host -- quick to respond and clear and concise with his communication. The price was more than right. I cannot say enough great things about this property and Angel. Recommended so very highly.

Responds fast! avg. 1 hour 26 minutes

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$160

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

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$149

Siesta Key- Beach Chic Retreat, Siesta Key 3 Bedroom 2 Bath Apartment

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 7

“This was the definition of home away from home” great value for your money...very cozy, with lots of new upgrades. Easy access to the beach and restaurants.

Responds fast! avg. 1 hour 29 minutes

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$268

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

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$149

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

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$107

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

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$289

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

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$188

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

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$197

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

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$163

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

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 8

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$206

"Cottage by the Sea" 1 Bedroom/ 1 Bath Across From Beach!!- · 3031, 3032

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 4

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$171

Seagrove

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$126

Holiday House 1

Siesta Key apartment

1 bedroom / 1 bathroom / sleeps 4

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$90

Perfect Getaway-2Bedroom/2Bath Steps from Beach with Pool Access!!- La Estrella

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

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$228

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.

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$103

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

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$205

Charming Siesta Key Condo, Walk to Beach, Pool

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 1 hour 44 minutes

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$117

Sea Club II

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 5

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$112

The Shells Villa - Next to Beach & Village

Siesta Key house

3 bedrooms / 3 bathrooms / sleeps 10

“Great Experience and Location!” We could not have been happier with our Experience at Shell Villa. Location to the Village was super close as described. Access to the beach was great both through the private walkway or the public access about two block away. The house was well stocked and the floor plan was perfect for our two families. Best place I have rented on SK in 5 years.

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$261

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

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$220

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

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$179

5 Bedroom Beachfront Home on Siesta Beach!! 49 Beach Rd

Siesta Key house

5 bedrooms / 3 bathrooms / sleeps 10

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$672

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

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$160

Siesta Key Condo, Crescent Arms, unit 605 South

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 20 minutes

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$221

Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs

Siesta Key house

2 bedrooms / 3 bathrooms / sleeps 6

“Fantastic house close to everything” We stayed in Siesta key for the first week of November. This house was beautiful and equipped with everything you could ever need especially the heated pool and hot tub. we walked a block every evening to the village and every morning two blocks to the beach. Will book again for sure

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$331

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

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$125

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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$63

Large Studio. Walk to Village. Couple Getaway!

Siesta Key apartment

/ 1 bathroom / sleeps 2

“gracious and spacious” Lovely home and great location to walk throughout Siesta Key Village and the beautiful sands of the beach!! We were able to have everyone together for a great vacation.

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$128

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

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$277

Luxury Village Townhouse w/ Gulf and Beach Views

Siesta Key townhouse

2 bedrooms / 2 bathrooms / sleeps 8

“A wonderful home in an equally wonderful location.” The home provides a truly enjoyable family situation. The quality of the furnishings is very nice, the living space is very well maintained and clean and my interaction with the owner was always timely and courteous. My wife and I shared the home with our 14 year old granddaughter during our stay and the quiet enjoyment of the pool and the easy 1-2 minute walk to the Gulf of Mexico and the 5 minute walk to the heart of Siesta Key Village made the location hard to beat. Except for our day trips no car was needed. This is our second stay in the home and we will look to reserving it for our next visit. There were absolutely no disappointments only wonderful experiences.

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$384

"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

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$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

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$185

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.

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$141

# 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

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$200

Newly Renovated Waterfront Condo w/Beach Access

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 4

“Awsome” We stayed at this condo for 7 days. We enjoyed our stay, everything was perfect , ocean just across the road , just a short walk, private beach access, condo itself was very well kept, beautiful kitchen, everything inside is new, appliances, showers, TV and couches, Pool right outside the condo. Deborah was very helpful with everything. Thank you!. I would come back here again.!

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$169

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 5

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$117

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