A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

Siesta Key Vacation Rentals

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Our top choices for Siesta Key vacation rentals

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,815 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is CA $155
CA $211 total
includes taxes & fees
Sep 2 - Sep 3
Tropical Beach Resorts

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (175 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is CA $269
CA $304 total
includes taxes & fees
Sep 2 - Sep 3
SeaSpray Resort

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,302 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
The price is CA $209
CA $260 total
includes taxes & fees
Sep 1 - Sep 2
Captiva Beach Resort

4. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,433 reviews)
"This place was perfect!"
United States
Kat
The price is CA $157
CA $178 total
includes taxes & fees
Sep 9 - Sep 10
Hibiscus Suites - Gateway to Siesta Key

5. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (384 reviews)
"Great place"
United States
Mario
The price is CA $115
CA $319 total
includes taxes & fees
Sep 11 - Sep 12
Tiny House Siesta

6. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (80 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is CA $157
CA $469 total
includes taxes & fees
Sep 2 - Sep 3
Siesta Key Island Rentals

7. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (206 reviews)
"The property was perfect. Walk to down town and the beach. Loved the provisions for the beach which made it so convenient. Room was super clean and overall the property was well maintained."
United States
Stephen
The price is CA $276
CA $389 total
includes taxes & fees
Sep 1 - Sep 2
The Inn On Siesta Key

8. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.4 out of 10, Exceptional, (39 reviews)
"The space was clean and well-equipped, and the host was easily reachable and responded quickly when I asked a question. The private beach access was nice. I would stay here again. "
United States
Natalie M.
The price is CA $97
CA $349 total
includes taxes & fees
Sep 1 - Sep 2
[Beach Elements] pool view withprivate beach access

9. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Thanks for a great stay, Jayme! Perfect location and extremely accurate Vrbo listing! Beds super comfy!"
United States
Sue H.
The price is CA $99
CA $391 total
includes taxes & fees
Sep 7 - Sep 8
[lounge like locals] walk to siesta beach +bikes

10. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (45 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is CA $132
CA $429 total
includes taxes & fees
Sep 1 - Sep 2
Siesta Heron Suites & Villas

11. Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (54 reviews)
"Perfect weekend getaway stay for my husband and I! The cottage had everything we needed, was thoroughly cleaned and location was perfect for restaurant hopping and beach going. Would definitely stay again!"
United States
Allie A.
The price is CA $134
CA $352 total
includes taxes & fees
Sep 1 - Sep 2
Siesta Key, Sea Horse Villa, Pool. Daily rentals

12. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (90 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is CA $138
CA $420 total
includes taxes & fees
Sep 1 - Sep 2
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

13. Modern Condo 2 minute walk to Beach- KING SIZE TEMPUR-PEDIC BED BEAUTIFUL POOL

Modern Condo 2 minute walk to Beach- KING SIZE TEMPUR-PEDIC BED BEAUTIFUL POOL
South Village
9.8 out of 10, Exceptional, (7 reviews)
"The host David was very accessible and accommodating. Some minor issues need attention, like faucets and shower."
United States
Peg S.
Modern Condo 2 minute walk to Beach- KING SIZE TEMPUR-PEDIC BED BEAUTIFUL POOL

14. [Sunny in Siesta] king bed + walk to beach

[Sunny in Siesta] king bed + walk to beach
South Village
9.6 out of 10, Exceptional, (14 reviews)
"Great location and accommodation. "
United States
ESTELEN
The price is CA $99
CA $344 total
includes taxes & fees
Sep 1 - Sep 2
[Sunny in Siesta] king bed + walk to beach

15. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
The price is CA $134
CA $352 total
includes taxes & fees
Sep 1 - Sep 2
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

16. Beachside Studio Located Across from Main Beach and Half Mile to Village

Beachside Studio Located Across from Main Beach and Half Mile to Village
Sarasota
8.8 out of 10, Excellent, (169 reviews)
"The rental had everything promised. The bed and couch were very comfortable. Everything was clean. Beach access was great. The chairs, cooler, and canopy were were just what was needed to maximize our enjoyment on a great beach."
United States
Karen G.
The price is CA $198
CA $365 total
includes taxes & fees
Sep 1 - Sep 2
Beachside Studio Located Across from Main Beach and Half Mile to Village

17. Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (47 reviews)
"Great place to stay"
United States
Brad S.
Siesta Key Village-Suite #1: A block to the Beach!

18. Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
South Village
9.8 out of 10, Exceptional, (34 reviews)
"Great stay."
United States
James J.
The price is CA $134
CA $297 total
includes taxes & fees
Sep 1 - Sep 2
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

19. Heart of Village: Dog-Friendly w/ Pool & Parking

Heart of Village: Dog-Friendly w/ Pool & Parking
Siesta Key Village
9.2 out of 10, Wonderful, (16 reviews)
"Love the place. Perfect location. Close to village, close to beach. Highly suggest and will definitely be back in the future. Host was very friendly and accommodating."
United States
Jeffrey B.
The price is CA $149
CA $493 total
includes taxes & fees
Sep 1 - Sep 2
Heart of Village: Dog-Friendly w/ Pool & Parking

20. Siesta Key APT On OceanW/FREE WIFI, BEACH AMENTITIES, ONSITE MANAGER, &LAUNDRY

Siesta Key APT On OceanW/FREE WIFI, BEACH AMENTITIES, ONSITE MANAGER, &LAUNDRY
Siesta Key
8.4 out of 10, Very good, (15 reviews)
"Great place to stay, very close to the beach and restaurants "
United States
Yeimy R.
The price is CA $124
CA $261 total
includes taxes & fees
Sep 5 - Sep 6
Siesta Key APT On OceanW/FREE WIFI, BEACH AMENTITIES, ONSITE MANAGER, &LAUNDRY
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

Find out more about Siesta Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Siesta Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Siesta Key?

Yes, we give you a choice of vacation rentals in Siesta Key close to Jim Neville Marine Preserve, or you can go with a more secluded option if you'd like a relaxing place to stay. Visitors to Siesta Key like the popular beaches and live music. You can also check out the entertainment venues while you're visiting.

What are some of the best vacation rentals in Siesta Key?

Siesta Key Island Rentals: Visitors like this Siesta Key vacation home rental. It comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind. Some other top choices in Siesta Key are Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf! and Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!.

How many vacation rentals are there in Siesta Key?

With 414 Expedia vacation rentals, you're sure to find just the right place for your Siesta Key stay.

What can I see and do in Siesta Key?

Siesta Key Beach and Shell Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jim Neville Marine Preserve. You’ll find favorite places to visit like Lido Beach and Venice Beach in the larger area.

What are vacation rentals like in Siesta Key?

Vacation rentals are private accommodations you can stay in for several days or longer in Siesta Key. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.