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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Condo Rentals in Siesta Key

Captiva Beach Resort
Front of property - evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1122)
"Everything was perfect with our stay. We will be back soon."
Captiva Beach Resort
Cozy condo in charming Sarasota Siesta key with boat dock
Terrace/patio

Cozy condo in charming Sarasota Siesta key with boat dock

10.0 out of 10, Exceptional, (2)
"Amazing getaway! The location by the water was perfect for relaxing by boat. Cozy and well-equipped, we loved every moment. Highly recommend for a peaceful, scenic retreat."
Cozy condo in charming Sarasota Siesta key with boat dock
Palm Bay Club Private Balcony Beach Side
Pool

Palm Bay Club Private Balcony Beach Side

2.0 star property
8.8 out of 10, Excellent, (13)
"Nice location, clean place, great communication even when our family hit some bumps with our trip. Overall highly recommend and and plan to return. "
Palm Bay Club Private Balcony Beach Side
Spectacular Beach View! Right on Beach! Amazing views!!
On the beach, sun-loungers

Spectacular Beach View! Right on Beach! Amazing views!!

9.8 out of 10, Exceptional, (143)
"I really appreciated the owner and her interest in making sure everything was perfect during our stay! She was awesome!"
Spectacular Beach View! Right on Beach! Amazing views!!
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
On the beach, sun-loungers

1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets

9.6 out of 10, Exceptional, (156)
"We could not have been happier with this location and its proximity to the beach and the pools. It was also close to great restaurants by locals who proudly serve great food!! "
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA
Beach nearby, beach umbrellas

2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA

9.2 out of 10, Wonderful, (68)
"Nice location lots of hurricane damage"
2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA
Amazing Condo! Restored from Hurricane!
On the beach, sun-loungers

Amazing Condo! Restored from Hurricane!

9.8 out of 10, Exceptional, (159)
"Quiet area with excellent beach access! Thank you"
Amazing Condo! Restored from Hurricane!
5 Minutes from Siesta Key!
Beach nearby, sun-loungers, beach towels

5 Minutes from Siesta Key!

9.6 out of 10, Exceptional, (33)
"Unit was clean, great location and comfortable. Communication was great. Would stay again. "
5 Minutes from Siesta Key!
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, (155)
"Beautiful Condo as listed with beautiful views. You can watch the sunrise right from your window or walk outside to the pool area. Karin was great communicating information needed prior to check in, or anytime if needed. Would def stay here again. "
PARADISE ! 2 bedroom 2 bathroom with incredible views
Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”
Fridge, microwave, oven, stovetop

Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”

10.0 out of 10, Exceptional, (56)
"Awesome! The view of the ocean was well appreciated from the balcony in the evenings. Beautiful! Thanks again for your hospitality."
Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”
#1 Siesta Key Beach -Super Clean -2 Level Townhouse -2Br/2.5 Bth- 5 Star- 1400sf
Beach nearby

#1 Siesta Key Beach -Super Clean -2 Level Townhouse -2Br/2.5 Bth- 5 Star- 1400sf

9.6 out of 10, Exceptional, (63)
"Perfect for what we wanted. Spent most of our time at the beach. They haveva dock in the back. Great for your coffee in the mornings, or kids to fish. Walkable to shops dunner,dinnet"
#1 Siesta Key Beach -Super Clean -2 Level Townhouse -2Br/2.5 Bth- 5 Star- 1400sf
Prime Beachfront with Views, Views, Views!
Property grounds

Prime Beachfront with Views, Views, Views!

9.6 out of 10, Exceptional, (82)
"The condo was clean, nicely decorated, spacious and very comfortable! It was steps from the beach and pool! The beach is absolutely beautiful! The pool was very nice! We would definitely stay here again! The beds are very comfortable and having two full bathrooms was so nice! We had a great week! "
Prime Beachfront with Views, Views, Views!
Steps away from the #1 beach! Spectacular views on the GIANT balcony!
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Steps away from the #1 beach! Spectacular views on the GIANT balcony!

10.0 out of 10, Exceptional, (122)
"We had a blast in Siesta Key! The owner, Amy, was great to work with! Loved her place and would definitely come back! "
Steps away from the #1 beach! Spectacular views on the GIANT balcony!
Luxury Condo Ground Floor Across the Street from the #1 Beach
TV

Luxury Condo Ground Floor Across the Street from the #1 Beach

9.0 out of 10, Wonderful, (76)
"Exactly as described-fun beach decor.every beach toy possible. Outdoor grill area was perfect with 2 gas ranges.2 minute walk to baby powder sand ,warm water,lots of sun.definitely coming back"
Luxury Condo Ground Floor Across the Street from the #1 Beach
Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach
On the beach

Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach

9.8 out of 10, Exceptional, (7)
"Great unit looking out at the ocean! You are right on the water and there's beach service, which is always nice. The unit looks like it was remodeled recently, and they have everything you need (towels, extra chairs, etc). It was a really great stay and would recommend it to anyone!"
Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach
Charm | Comfy | Tiki | Pool Private Beach
A heated pool

Charm | Comfy | Tiki | Pool Private Beach

9.6 out of 10, Exceptional, (188)
"It was very cozy, and we loved it and will be staying there again."
Charm | Comfy | Tiki | Pool Private Beach
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, (10)
"This is a great place to stay. Would definitely book again!"
Stunning Siesta Key Beach Views from 2 Bedroom Condo!
Sea Club 2 - Relaxing Siesta Beach Key Condo Rental - Mermaids Rest
Beach nearby

Sea Club 2 - Relaxing Siesta Beach Key Condo Rental - Mermaids Rest

9.6 out of 10, Exceptional, (42)
"Had a great time staying here . It was clean,and had everything we needed. Great beach access close to everything. Would stay there again"
Sea Club 2 - Relaxing Siesta Beach Key Condo Rental - Mermaids Rest
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, (11)
"I have been coming to Siesta Key, Florida for over 40 years. This by far has been one of my most comfortable accommodations, and this condo exceeded all of our expectations. It was exceptionally clean and very comfortable. We also loved how modern and updated the unit was and how it was decorated. It is conveniently located walking distance from the beach, and to many amazing restaurants and tiki bars, which was so convenient. I will be recommending this condo unit to all of my family and...
Brand new to the market! Siesta Key 2 Br/2ba- Locally managed Welcome!
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, (15)
"We had a wonderful stay at Bay Oaks! The unit and location were great, just as described. We had some communication issues on getting the check-in information which caused some stress; however, we got it resolved just prior to arrival."
Updated Siesta Key Vacation Rental at Bay Oaks
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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Top Siesta Key Hotel Reviews

Siesta Key Island Rentals

Siesta Key Island Rentals

10/10 Excellent
"This is the best place to stay in Siesta Key and overall best place. Everything was very clean, the AC works so good specially during hot weather the room stays very cold. The bed was so comfortable and cleaned. This place has the best customer service I have ever experienced. Very sweet, helpful, and caring. There was a night were we forgot our password getting in and I sent them a email since it was after hours saying we needed the password and they called immediately after I sent the email, Checking if we were okay and if we needed help. This place is across from the beach like a 5 minute walk very close and the village is also right around the corner. I recommend this place 100%."
Esther 4-night trip
Posted 2 days ago
Siesta Key Island Rentals