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Siesta Key Rentals with Pools

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846 beach rentals in Siesta Key with pools

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 33 minutes

Match: Swimming pool

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Price per night from

$263

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

Responds fast! avg. 2 hours 17 minutes

Match: Swimming pool

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Price per night from

$126

Walk to Crescent Beach, Wifi, Bay Views From Lanai, Heated Pool, Tennis, On Trol

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$122

Across the street from Siesta Key Beach, Gulf View, Pool, Tennis, Parking, Balco

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$179

Siesta Key Beach is Across the Street, Partial Water Views, WiFi, Renovated, Ove

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$131

Complex on the Bay, Walk to Beaches, Heated Pool, Wifi, Ground Floor, Renovated,

Siesta Key condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$119

Siesta Key Condo w/Private Beach Access, Wifi Included, Heated Pool, Tennis & B

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. 3 minutes

Match: Swimming pool

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Price per night from

$134

New Owners & Superbly Renovated, Walk to Crescent Beach, Free Cable/Wifi, Heate

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$149

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

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$251

Canal Home on Siesta Key w/ Pool, Wifi, Renovated 1950 Style Sarasota School of

Siesta Key house

4 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$314

Walk to Siesta Beach, Heated Pool, Wifi, Renovated Ground Floor Unit, Covered Pa

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$131

Sea Shell Condo-Right On Crescent Beach-Siesta Key

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 34 minutes

Match: Swimming pool

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Price per night from

$355

Beautifully Renovated & Modern, Wifi, Harbor Towers, 3 bedroom with Den

Siesta Key apartment

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$155

Chinaberry 436 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$264

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$165

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

Siesta Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$541

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.

Match: Swimming pool

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Price per night from

$263

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. 3 hours 5 minutes

Match: Swimming pool

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Price per night from

$264

Buttonwood 462 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$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.

Responds fast! avg. 1 hour 26 minutes

Match: Swimming pool

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Price per night from

$189

Private Beach, Full Gulf Views, Wifi/Cable, Heated Swimming Pool Overlooking Oce

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$225

LuLu's Leatherback Walk to Beach & Village, Heated Pool, WiFi, Barbecue Station,

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$213

Responds fast! avg. 2 hours 50 minutes

Match: Swimming pool

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Price per night from

$184

Doveplum 621 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$167

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

1 bedroom / 1 bathroom / sleeps 4

“Amazing!!!!” Bea’s rental in Sienna Park was an amazing place to stay. The new free form pool is just steps from your door. She has everything you need for a luxurious vacation. Best place we have stayed..... It is also only minutes from Siesta Key beach. I will definitely book with her again.

Match: Swimming pool

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Price per night from

$86

Buttonwood 477 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

All filters match

Price per night from

$290

Firethorn 320 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Match: Swimming pool

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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

Match: Swimming pool

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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

Responds fast! avg. 6 minutes

Match: Swimming pool

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Price per night from

$263

Walk to Beach, WiFi, Heated Pool, Screened Lanai Overlooks Pool, Fishing Pier, T

Siesta Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Match: Swimming pool

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Price per night from

$103

Beach Across the Street, Partial Gulf Views, Wifi, Tennis Courts, Community Poo

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Match: Swimming pool

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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

Match: Swimming pool

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Price per night from

$142

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

Siesta Key apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 18 minutes

Match: Swimming pool

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Price per night from

$228

Chinaberry 416 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

All filters match

Price per night from

$264

Chinaberry 943 at Midnight Cove Siesta Key

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$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♡

Responds fast! avg. 1 hour 34 minutes

Match: Swimming pool

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Price per night from

$252

Luxurious 2 BR Condo - Short Walk to Siesta Beach, #1 in The USA

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: Swimming pool

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Price per night from

$156

Firethorn 610 at Midnight Cove Siesta Key, FL.

Siesta Key apartment

2 bedrooms / 1 bathroom / sleeps 6

Match: Swimming pool

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Price per night from

$142

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