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

Siesta Key Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (6,033 reviews)
"Great resort and location!"
United States
Christine
$169 nightly
The price is $190
Nov 4 - Nov 5
Total with taxes and fees
Tropical Beach Resorts
A bedroom with a view of a swimming pool and outdoor seating.

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (205 reviews)
"The room was clean and the staff were very kind."
United States
Geraldine
$204 nightly
The price is $230
Nov 8 - Nov 9
Total with taxes and fees
SeaSpray Resort
A compact living space with a kitchen, a dining area, and a sofa with cushions.

3. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (391 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
Nov 18 - Nov 19
Total with taxes and fees
Tiny House Siesta
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, (2,479 reviews)
"This place was perfect!"
United States
Kat
$150 nightly
The price is $169
Nov 4 - Nov 5
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

5. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,332 reviews)
"We liked the clean room, friendly staff, close to the beach and outdoor amenities."
United States
Andriy
$188 nightly
The price is $210
Nov 10 - Nov 11
Total with taxes and fees
Captiva Beach Resort
An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

6. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
$307 nightly
The price is $347
Nov 4 - Nov 5
Total with taxes and fees
Beach Tree Cottage,Walk To Beach& Siesta
A house with a gravel driveway, two blue chairs facing the front, and a porch with a green chair and a red umbrella.

7. 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.
$216 nightly
The price is $242
Nov 4 - Nov 5
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A hot tub surrounded by a wooden fence, with lounge chairs and an umbrella in the background.

8. PinkMango Cottage Steps to Beach&Village

PinkMango Cottage Steps to Beach&Village
2.0 star property
Siesta Key Village
$344 nightly
The price is $388
Nov 4 - Nov 5
Total with taxes and fees
PinkMango Cottage Steps to Beach&Village
A patio with a sun lounger, a table with chairs, and an umbrella.

9. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
$382 nightly
The price is $432
Nov 5 - Nov 6
Total with taxes and fees
Beach View 100ft To Beach and SPA
Two blue chairs facing a house with a porch, surrounded by palm trees and a gravel driveway.

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

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (55 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.
$216 nightly
The price is $242
Nov 4 - Nov 5
Total with taxes and fees
Siesta Key, Sea Horse Villa, Pool. Daily rentals
A room with a bunk bed, a small desk, and a TV.

11. Tiny House Calypso with 1st floor sleeping

Tiny House Calypso with 1st floor sleeping
Sarasota
9.0 out of 10, Wonderful, (11 reviews)
"Third time here and best visit will book again in future "
United States
Desirae
$153 nightly
The price is $171
Nov 4 - Nov 5
Total with taxes and fees
Tiny House Calypso with 1st floor sleeping
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.

12. 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
$276 nightly
The price is $312
Nov 4 - Nov 5
Total with taxes and fees
Siesta Heron Suites & Villas
A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

13. [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)
"Beautiful stay , I walked each day to the beach and really is 13 min walk to get to the beach - pickle ball courts available to play in the morning -the beach is excellent - the place have everything we need beds and shower was really nice -Really excellent we will come back."
United States
Moreixa C.
$296 nightly
The price is $302
Nov 8 - Nov 9
Total with taxes and fees
[lounge like locals] walk to siesta beach +bikes
A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

14. 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, (15 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
$365 nightly
The price is $381
Nov 4 - Nov 5
Total with taxes and fees
Island Villa | Cozy Beach Retreat | Walk to Village
A street view with a building labeled 'SISTA KEY UNIVERSITY' and a palm tree in the foreground.

15. Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (79 reviews)
"Great stay"
United States
Allison H.
$365 nightly
The price is $398
Nov 5 - Nov 6
Total with taxes and fees
Siesta Key Village-Suite #3: A Block to the Beach!
A modern living room with a grey sofa, two round side tables, a world map on the wall, and a view of a pool and outdoor seating area.

16. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (45 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.
$290 nightly
The price is $297
Nov 15 - Nov 16
Total with taxes and fees
[Beach Elements] pool view withprivate beach access
A compact living space with a kitchenette, a dining area, and a bedroom.

17. Studio Retreat Across the Street from Beautiful Siesta Key Beach

Studio Retreat Across the Street from Beautiful Siesta Key Beach
Siesta Key
9.0 out of 10, Wonderful, (168 reviews)
"No oven, but it was an excellent place to stay!"
United States
Brittany K.
$278 nightly
The price is $310
Nov 16 - Nov 17
Total with taxes and fees
Studio Retreat Across the Street from Beautiful Siesta Key Beach
A small, single-story building with a porch, surrounded by tropical vegetation.

18. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
$397 nightly
The price is $449
Nov 6 - Nov 7
Total with taxes and fees
BlueDolphin Cottage Walk To Siesta Beach
A cozy cabin interior with a sofa, a television, and a 'Welcome Visitors' sign.

19. Tiny House Green Lifeguard Stand - sleeps 5

Tiny House Green Lifeguard Stand - sleeps 5
Sarasota
9.4 out of 10, Exceptional, (33 reviews)
"Very clean & tidy! The house stayed cool & comfortable the whole night! My husband & I enjoyed this unique place & would definitely book again!"
United States
Jennifer S.
$161 nightly
The price is $180
Nov 4 - Nov 5
Total with taxes and fees
Tiny House Green Lifeguard Stand - sleeps 5
A hot tub surrounded by a wooden fence, with lounge chairs and an umbrella in the background.

20. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
$417 nightly
The price is $471
Nov 6 - Nov 7
Total with taxes and fees
Yellow Palm Cottage, Heart of Siesta Key
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

The Ringling Beach House

The Ringling Beach House

10/10 Excellent
"Will absolutely be returning!!!!"
Rhiannon 4-night trip
Posted 17 hours ago
The Ringling Beach House

Price trends for vacation rentals in Siesta Key

Less expensive
More expensive
This month
Next month
May
March
$385
$428
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 $190 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.