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

Siesta Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Siesta Key vacation rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,943 reviews)
"Amazing resort,"
United States
kurt
$184 nightly
The price is $208
Oct 6 - Oct 7
Total with taxes and fees
Tropical Beach Resorts
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (188 reviews)
"Great place with a bunch of little touches that put it above and beyond"
United States
Rafe
$209 nightly
The price is $236
Nov 4 - Nov 5
Total with taxes and fees
SeaSpray Resort
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,316 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
$177 nightly
The price is $197
Oct 6 - Oct 7
Total with taxes and fees
Captiva Beach Resort
An outdoor patio with a grill, white chairs, and a red umbrella.

4. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,458 reviews)
"This place was perfect!"
United States
Kat
$127 nightly
The price is $144
Oct 7 - Oct 8
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
A pair of stacked front-loading washing machines in a commercial setting.

5. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
$322 nightly
The price is $364
Oct 8 - Oct 9
Total with taxes and fees
Beach View 100ft To Beach and SPA
A compact living space with a kitchen, a dining area, and a sofa with cushions.

6. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (387 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
$181 nightly
The price is $205
Oct 8 - Oct 9
Total with taxes and fees
Tiny House Siesta
A covered outdoor area with a wooden table and chairs, a white door, and a yellow wall.

7. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
Yellow Palm Cottage, Heart of Siesta Key
A living room with a sofa, armchair, coffee table, and a potted plant.

8. Siesta Vibe Pool Walk To Crescent Beach

Siesta Vibe Pool Walk To Crescent Beach
2.0 star property
South Village
$358 nightly
The price is $405
Oct 6 - Oct 7
Total with taxes and fees
Siesta Vibe Pool Walk To Crescent Beach
A beach with a small cluster of palm trees in the foreground and a sandy beach extending to the horizon.

9. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (43 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.
$253 nightly
The price is $257
Oct 8 - Oct 9
Total with taxes and fees
[Beach Elements] pool view withprivate beach access
A modern bedroom with a bed, a bedside table, a round dining table with chairs, and a large window with curtains.

10. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (34 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
$258 nightly
The price is $262
Oct 6 - Oct 7
Total with taxes and fees
[escape to paradise] siesta key beach getaway
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

11. Dolphin Villa - Pool - Steps to Siesta Key Village

Dolphin Villa - Pool - Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
$376 nightly
The price is $395
Oct 13 - Oct 14
Total with taxes and fees
Dolphin Villa - Pool - Steps to Siesta Key Village
A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

12. Island Villa | Cozy Beach Retreat | Walk to Village

Island Villa | Cozy Beach Retreat | Walk to Village
Siesta Key Village
8.4 out of 10, Very good, (14 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
$389 nightly
The price is $405
Oct 20 - Oct 21
Total with taxes and fees
Island Villa | Cozy Beach Retreat | Walk to Village
A two-story building with a flat roof, a front porch, and a gravel driveway.

13. Beautiful,Cozy 3Bed/2 Siesta Key home on Ocean blvd, close to village, beaches,

Beautiful,Cozy 3Bed/2 Siesta Key home on Ocean blvd, close to village, beaches,
Siesta Key
9.0 out of 10, Wonderful, (35 reviews)
"Place was roomy and comfortable. Nice location. We took our bikes and could easily get around. (Great not having to look for parking!)"
United States
Klay R.
$278 nightly
The price is $310
Oct 6 - Oct 7
Total with taxes and fees
Beautiful,Cozy 3Bed/2 Siesta Key home on Ocean blvd, close to village, beaches,
A beach with waves and a bird flying near the shore.

14. The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
Sarasota
10.0 out of 10, Exceptional, (4 reviews)
"Traveled with my kids and this place was so great! Super cute and comfortable. We loved the Mermaid Tiny House."
United States
Kadina A.
$157 nightly
The price is $175
Oct 12 - Oct 13
Total with taxes and fees
The Mermaid at Tiny House Siesta
A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

15. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (46 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
$280 nightly
The price is $316
Oct 8 - Oct 9
Total with taxes and fees
Siesta Heron Suites & Villas
A pink mobile home with a patio area featuring a table and chairs, a striped umbrella, and a surfboard leaning against the house.

16. Tiny Coral Oasis- beachy tiny house for your getaway

Tiny Coral Oasis- beachy tiny house for your getaway
Sarasota
9.0 out of 10, Wonderful, (20 reviews)
"Cute tiny house Clean and comfortable Had a great time"
United States
DeAnna T.
$166 nightly
The price is $185
Oct 6 - Oct 7
Total with taxes and fees
Tiny Coral Oasis- beachy tiny house for your getaway
A jet ski with 'FL 4210 RR' on the side, a person and a child on it, and a body of water with houses in the background.

17. 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.
$226 nightly
The price is $252
Oct 6 - Oct 7
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A beach with clear turquoise water and gentle waves.

18. 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.
$263 nightly
The price is $293
Oct 11 - Oct 12
Total with taxes and fees
Siesta Key, Sea Horse Villa, Pool. Daily rentals
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

19. Everglades Villa • Sleeps 8 • Walk to Siesta Beach

Everglades Villa • Sleeps 8 • Walk to Siesta Beach
Siesta Key Village
9.0 out of 10, Wonderful, (15 reviews)
"We loved staying here for my bachelorette!"
United States
Kelsey E.
$408 nightly
The price is $425
Oct 6 - Oct 7
Total with taxes and fees
Everglades Villa • Sleeps 8 • Walk to Siesta Beach
A beach with a clear sky and calm sea.

20. 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.
$334 nightly
The price is $352
Oct 7 - Oct 8
Total with taxes and fees
Heart of Village: Dog-Friendly w/ Pool & Parking
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 Beachside Villas

Siesta Key Beachside Villas

10/10 Excellent
"This unit/studio was very nice and clean, a little small, but enough for 2 people spending 2 nights. The resort is nice, with a pool and it’s close to the beach. The area is very walkable with nice restaurants and shops"
Ana K 2-night trip
Posted 7 hours ago
Siesta Key Beachside Villas

Price trends for vacation rentals in Siesta Key

Less expensive
More expensive
This month
Next month
May
March
$339
$385
Month
Price
January
$418
February
$509
March
$542
April
$406
May
$339
June
$398
July
$403
August
$348
September
$343
October
$339
November
$385
December
$428
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Siesta Key. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Siesta Key

Everything you need to know about Siesta Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Siesta Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Siesta Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Siesta Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Siesta Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Siesta Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $197 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Siesta Key rentals

At Expedia, we put the best Siesta Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Siesta Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Siesta Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Siesta Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 St. Boniface Episcopal Church Labyrinth, 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 give good reviews to this Siesta Key vacation home rental, which comes with free 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. Another good choice for your trip to Siesta Key is Siesta Heron Suites & Villas.

How many vacation rentals are there in Siesta Key?

With 401 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 Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jim Neville Marine Preserve. While here, Safe Harbor Siesta Key and Point of Rocks are other places worth a visit.

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.