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

Siesta Key Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Siesta Key vacation rentals

Property grounds

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,809 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is ￥17,802
￥24,276 total
includes taxes & fees
Aug 31 - Sep 1
Tropical Beach Resorts
Superior Suite, 2 Bedrooms

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 ￥32,647
￥36,891 total
includes taxes & fees
Sep 8 - Sep 9
SeaSpray Resort
Front of property - evening/night

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 ￥24,090
￥29,935 total
includes taxes & fees
Sep 1 - Sep 2
Captiva Beach Resort
Pool

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 ￥18,098
￥20,452 total
includes taxes & fees
Aug 31 - Sep 1
Hibiscus Suites - Gateway to Siesta Key
Cabin (Tiny House - The Siesta) | Living area

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 ￥13,432
￥36,893 total
includes taxes & fees
Sep 13 - Sep 14
Tiny House Siesta
5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

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 ￥15,337
￥50,761 total
includes taxes & fees
Aug 31 - Sep 1
Siesta Key Island Rentals
Beach

7. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (205 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 ￥30,785
￥43,650 total
includes taxes & fees
Aug 31 - Sep 1
The Inn On Siesta Key
Beach

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 ￥11,213
￥40,319 total
includes taxes & fees
Sep 1 - Sep 2
[Beach Elements] pool view withprivate beach access
Private kitchen

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 ￥12,037
￥45,344 total
includes taxes & fees
Aug 31 - Sep 1
[lounge like locals] walk to siesta beach +bikes
House, Lakeside | Living area

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 ￥14,495
￥48,580 total
includes taxes & fees
Sep 1 - Sep 2
Siesta Heron Suites & Villas
Beach

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 ￥15,388
￥40,846 total
includes taxes & fees
Aug 31 - Sep 1
Siesta Key, Sea Horse Villa, Pool. Daily rentals
Beach

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 ￥15,849
￥48,679 total
includes taxes & fees
Aug 31 - Sep 1
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Beach

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
Beach

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)
The price is ￥11,378
￥39,722 total
includes taxes & fees
Sep 1 - Sep 2
[Sunny in Siesta] king bed + walk to beach
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 ￥15,388
￥40,846 total
includes taxes & fees
Aug 31 - Sep 1
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
Beach

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 ￥22,848
￥42,219 total
includes taxes & fees
Sep 1 - Sep 2
Beachside Studio Located Across from Main Beach and Half Mile to Village
Beach

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!
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 ￥15,388
￥34,458 total
includes taxes & fees
Aug 31 - Sep 1
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
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 ￥17,130
￥57,114 total
includes taxes & fees
Aug 31 - Sep 1
Heart of Village: Dog-Friendly w/ Pool & Parking
Exterior detail

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 ￥15,849
￥31,943 total
includes taxes & fees
Aug 31 - Sep 1
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Siesta Key Hotel Reviews

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"N/A"
Silvia 1-night trip
Posted 11 hours ago
Tropical Beach Resorts

Find out more about Siesta Key

Search for holiday rentals in Siesta Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Siesta Key using one of the methods below:

  • View our selection of featured holiday rentals in Siesta Key
  • Use the map to find apartments and other holiday homes in the Siesta Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Siesta Key while they last

Look no further and take a look at our great range of rental properties in Siesta Key!

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.