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Our top choices for Siesta Key holiday rentals

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (69 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
The price is £272
includes taxes & fees
23 Jun - 24 Jun
Siesta Key Island Rentals

SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!

SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!
Siesta Key
9.4 out of 10, Exceptional, (31 reviews)
"Great place close to everything"
United States
Tracey M.
The price is £364
includes taxes & fees
7 Jul - 8 Jul
SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,265 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
The price is £169
includes taxes & fees
6 Jul - 7 Jul
Captiva Beach Resort

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (31 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is £233
includes taxes & fees
22 Jun - 23 Jun
[escape to paradise] siesta key beach getaway

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (33 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 £213
includes taxes & fees
23 Jun - 24 Jun
[Beach Elements] pool view withprivate beach access

Walk to the Beach | Osprey Villa | Siesta Key

Walk to the Beach | Osprey Villa | Siesta Key
Siesta Key Village
9.8 out of 10, Exceptional, (19 reviews)
"Host was very helpful. The apt was very comfy"
United States
Barbara B.
The price is £249
includes taxes & fees
21 Jun - 22 Jun
Walk to the Beach | Osprey Villa | Siesta Key

Island Villa - Cozy Beach Retreat with Private dock

Island Villa - Cozy Beach Retreat with Private dock
Siesta Key Village
8.4 out of 10, Very good, (13 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
The price is £304
includes taxes & fees
21 Jun - 22 Jun
Island Villa - Cozy Beach Retreat with Private dock

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
South Village
8.8 out of 10, Excellent, (87 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
The price is £272
includes taxes & fees
19 Jul - 20 Jul
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

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, (76 reviews)
"Perfect location, super clean.comfortable"
United States
matthew w.
The price is £308
includes taxes & fees
21 Jun - 22 Jun
Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (43 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is £262
includes taxes & fees
24 Jun - 25 Jun
Siesta Heron Suites & Villas

Lulu's Cozy Beach Cottage #2 | 5 Min. Walk to Beach | Dog OK | Pool | $185 Free Activities Daily!

Lulu's Cozy Beach Cottage #2 | 5 Min. Walk to Beach | Dog OK | Pool | $185 Free Activities Daily!
Sarasota
10.0 out of 10, Exceptional, (33 reviews)
"This is a great cozy place for us to stay - we have enjoyed our stay very much! and the location is great so you do not have to be in the middle of the condo area. We will stay again "
United States
Kristin S.
The price is £439
includes taxes & fees
21 Jun - 22 Jun
Lulu's Cozy Beach Cottage #2 | 5 Min. Walk to Beach | Dog OK | Pool | $185 Free Activities Daily!

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio
Siesta Key Village
9.8 out of 10, Exceptional, (11 reviews)
The price is £242
includes taxes & fees
7 Jul - 8 Jul
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

2 Bedroom 2 Bath home near Siesta Key Beach

2 Bedroom 2 Bath home near Siesta Key Beach
Sarasota
8.6 out of 10, Excellent, (40 reviews)
"Great little place -perfect for a few days in siesta "
United States
Linda K.
The price is £234
includes taxes & fees
21 Jun - 22 Jun
2 Bedroom 2 Bath home near Siesta Key Beach

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, (14 reviews)
"We enjoyed our stay at Everglades Villa. The location was the best feature as we were able to walk to Siesta Key Village and the beach. "
United States
Lisa S.
The price is £381
includes taxes & fees
24 Jun - 25 Jun
Everglades Villa • Sleeps 8 • Walk to Siesta Beach

House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!
South Village
9.2 out of 10, Wonderful, (139 reviews)
"The condo was clean, modern and comfortable for our stay in Siesta. The beach was beautiful and the location was super convenient with restaurants and bars within walking distance. We would highly recommend!"
United States
Sandy M.
The price is £598
includes taxes & fees
23 Jun - 24 Jun
House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

Tiny House Green Lifeguard Stand - sleeps 5

Tiny House Green Lifeguard Stand - sleeps 5
Sarasota
9.4 out of 10, Exceptional, (32 reviews)
"The area is quiet. The house is in a side road near a strip plaza. It’s cute and good for the tiny home experience. The microwave in our home looked pretty damaged on the inside. We did not use it but the stove top worked great!"
United States
JONELL
The price is £152
includes taxes & fees
22 Jun - 23 Jun
Tiny House Green Lifeguard Stand - sleeps 5

Siesta Key Studio close to beaches, city, and airport.

Siesta Key Studio close to beaches, city, and airport.
Siesta Key
8.4 out of 10, Very good, (12 reviews)
"Fantastic experience, great host, and close to everything!"
United States
Shannon
The price is £137
includes taxes & fees
22 Jun - 23 Jun
Siesta Key Studio close to beaches, city, and airport.

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is £408
includes taxes & fees
5 Jul - 6 Jul
The Inn On Siesta Key

Gulf Villa - 3 min to #1 Beach - Pool

Gulf Villa - 3 min to #1 Beach - Pool
Siesta Key Village
9.0 out of 10, Wonderful, (15 reviews)
"Very cute & clean. Great location!"
United States
Nannette
The price is £428
includes taxes & fees
7 Jul - 8 Jul
Gulf Villa - 3 min to #1 Beach - Pool

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (370 reviews)
"Loved the tiny house will stay there again!"
United States
Nydia
The price is £165
includes taxes & fees
24 Jun - 25 Jun
Tiny House Siesta
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

Everything you need to know about Siesta Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Siesta Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Siesta Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Siesta Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Siesta Key holiday rentals we have selected for you start as low as £164 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Siesta Key rentals

At Expedia, we put the best Siesta Key holiday 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 holiday.

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 holiday rental in Siesta Key?

Yes, there are holiday rentals in Siesta Key close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Siesta Key has to offer?

Siesta Key Island Rentals: This highly rated holiday home rental in Siesta Key comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Siesta Key is 3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport.

How many holiday rentals are there in Siesta Key?

With 417 Expedia holiday rentals, you're guaranteed to find just the right place for your Siesta Key stay.

What can I see and do in Siesta Key?

Siesta Key Beach and Turtle Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jim Neville Marine Preserve. You’ll find favourite places to visit such as Lido Beach and St. Armands Circle in the wider area.

What are holiday rentals like in Siesta Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Siesta Key. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family trip or a small group gathering.