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Check prices for these dates

Next weekend
20 Jun - 22 Jun
In two weeks
27 Jun - 29 Jun
In one month
11 Jul - 13 Jul
In two months
8 Aug - 10 Aug

Featured Condo Rentals in Siesta Key and around

Captiva Beach Resort
Front of property – evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1104)
"Great property! The room looked brand new. Was very clean!"
Captiva Beach Resort
Brand new to the market! Siesta Key 2 Br/2ba- Locally managed Welcome!
Sun-loungers, beach towels

Brand new to the market! Siesta Key 2 Br/2ba- Locally managed Welcome!

10.0 out of 10, Exceptional, (5)
Brand new to the market! Siesta Key 2 Br/2ba- Locally managed Welcome!
Cozy condo in charming Sarasota Siesta key with boat dock
Fridge, microwave, oven, stovetop

Cozy condo in charming Sarasota Siesta key with boat dock

Cozy condo in charming Sarasota Siesta key with boat dock
5 Minutes from Siesta Key!
Beach nearby, sun-loungers, beach towels

5 Minutes from Siesta Key!

9.6 out of 10, Exceptional, (27)
"My sister and I were in Sarasota area to see the Orioles play for Spring Training! This was a great place to stay. Had a wonderful time!"
5 Minutes from Siesta Key!
Siesta Key GULF SIDE #95 - Serene Private Condo, 3 Pools, Jamaica Royale
Outdoor pool, a heated pool

Siesta Key GULF SIDE #95 - Serene Private Condo, 3 Pools, Jamaica Royale

10.0 out of 10, Exceptional, (84)
"Amazing time and place."
Siesta Key GULF SIDE #95 - Serene Private Condo, 3 Pools, Jamaica Royale
Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..
On the beach

Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..

10.0 out of 10, Exceptional, (3)
"The rental was spacious and very clean!!I would definitely stay here again. Place looked exactly like the pictures!! "
Gulfside No Roads to Cross 1-bedroom condo with AC, WiFi On Siesta Key Beach..
PARADISE ! 2 bedroom 2 bathroom with incredible views
A heated pool

PARADISE ! 2 bedroom 2 bathroom with incredible views

9.8 out of 10, Exceptional, (151)
"Property was exactly what we expected and needed. "
PARADISE ! 2 bedroom 2 bathroom with incredible views
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
On the beach, sun-loungers, beach towels

Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building

9.8 out of 10, Exceptional, (250)
"We'll maintained and comfortable condo on the beach. We thoroughly enjoyed our time in the unit. It's in a beautiful location."
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
PALM BAY 5th floor ON THE BEACH Sunsets from the open lanai, Two Queen beds.
On the beach, sun-loungers, beach towels

PALM BAY 5th floor ON THE BEACH Sunsets from the open lanai, Two Queen beds.

10.0 out of 10, Exceptional, (77)
"Very nice unit and easy access to a beautiful beach!"
PALM BAY 5th floor ON THE BEACH Sunsets from the open lanai, Two Queen beds.
Amazing Condo! Restored from Hurricane!
On the beach, sun-loungers

Amazing Condo! Restored from Hurricane!

9.8 out of 10, Exceptional, (154)
"Quiet area with excellent beach access! Thank you"
Amazing Condo! Restored from Hurricane!
Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway
On the beach

Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway

9.4 out of 10, Exceptional, (57)
"Will stay again!"
Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
Beach nearby, sun-loungers, beach towels

Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key

9.2 out of 10, Wonderful, (65)
"The above and beyond accommodations given to us under extenuating circumstances, rarely occurs. To Kelli, you are an amazing human and I thank you profusely. Would love to stay again !!!!"
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Beach nearby, sun-loungers, beach towels

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

9.8 out of 10, Exceptional, (82)
"Had a great trip! Clean, quiet & great location!"
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Sun-loungers, beach towels

Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

10.0 out of 10, Exceptional, (6)
"Amazing Condo! Right across the street from the best beach in the YSA!"
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Great Gulf View! Steps to the No.1 Beach in a 2,759 sqft luxury townhome
Exterior

Great Gulf View! Steps to the No.1 Beach in a 2,759 sqft luxury townhome

10.0 out of 10, Exceptional, (64)
"Great family wedding spot"
Great Gulf View! Steps to the No.1 Beach in a 2,759 sqft luxury townhome
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
Pool

Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!

9.8 out of 10, Exceptional, (74)
"We had a great stay"
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
Spacious Penthouse 3bd/3bath, On the Beach, Great Views!
On the beach

Spacious Penthouse 3bd/3bath, On the Beach, Great Views!

10.0 out of 10, Exceptional, (157)
"We love to stay in this area of Siesta Key as it's much less crowded and easy access to get off the Key. LARGE condo with room for everyone! Super easy access to the beach. Modern and clean, comfortable bed and kitchen is as fully stocked as your own. Would stay again!"
Spacious Penthouse 3bd/3bath, On the Beach, Great Views!
Luxury condo located directly on Siesta Key Beach
On the beach

Luxury condo located directly on Siesta Key Beach

9.4 out of 10, Exceptional, (13)
"It was just what we needed.. a nice place to stay"
Luxury condo located directly on Siesta Key Beach
Updated Siesta Key Vacation Rental at Bay Oaks
A heated pool

Updated Siesta Key Vacation Rental at Bay Oaks

9.0 out of 10, Wonderful, (14)
"The condo was very clean and comfortable. "
Updated Siesta Key Vacation Rental at Bay Oaks
Stunning Siesta Key Beach Views from 2 Bedroom Condo!
TV

Stunning Siesta Key Beach Views from 2 Bedroom Condo!

9.6 out of 10, Exceptional, (9)
"This is a great place to stay. Would definitely book again!"
Stunning Siesta Key Beach Views from 2 Bedroom Condo!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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