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

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Our top choices for Siesta Key holiday rentals

1. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (180 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
The price is £174
includes taxes & fees
22 Sept - 23 Sept
SeaSpray Resort

2. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,897 reviews)
"This place is awesome, super clean close to the beach and the pool small But completely renovated and great"
United States
Diana
The price is £133
includes taxes & fees
27 Sept - 28 Sept
Tropical Beach Resorts

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,450 reviews)
"This place was perfect!"
United States
Kat
The price is £93
includes taxes & fees
20 Sept - 21 Sept
Hibiscus Suites - Gateway to Siesta Key

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,307 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is £143
includes taxes & fees
20 Sept - 21 Sept
Captiva Beach Resort

5. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (208 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 Inn On Siesta Key

6. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.4 out of 10, Exceptional, (81 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is £247
includes taxes & fees
30 Sept - 1 Oct
Siesta Key Island Rentals

7. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (385 reviews)
"Great place"
United States
Mario
The price is £156
includes taxes & fees
5 Oct - 6 Oct
Tiny House Siesta

8. ⭐️ Luxury Coastal Retreat, 60 Steps to World-Famous Siesta Key Beach! ⭐️

⭐️ Luxury Coastal Retreat, 60 Steps to World-Famous Siesta Key Beach! ⭐️
Siesta Key
9.8 out of 10, Exceptional, (95 reviews)
"I recommend it 100%. A fantastic vacation for family and friends. I loved the house; everything was very clean, and everything you need is available. It’s the best beach I’ve ever visited, and the view from the house is spectacular. Communication with the host was easy. We definitely want to come back."
United States
Yudisney A.
The price is £827
includes taxes & fees
20 Sept - 21 Sept
⭐️ Luxury Coastal Retreat, 60 Steps to World-Famous Siesta Key Beach! ⭐️

9. 🌷 Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach

🌷 Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach
Siesta Key
9.6 out of 10, Exceptional, (104 reviews)
"Very close to the beach and convenient. Clean. Easy for my fiance and I for a couple of days"
United States
Courtney
The price is £374
includes taxes & fees
21 Sept - 22 Sept
🌷 Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach

10. 🌷Steps to Siesta Beach, Chic Studio, Pool & Patio

🌷Steps to Siesta Beach, Chic Studio, Pool & Patio
Siesta Key
9.6 out of 10, Exceptional, (88 reviews)
"Great time in siesta key for a long weekend. Have stayed at this property many times. Always great experience and location to the beach and short walk into the village"
United States
Colleen O.
The price is £334
includes taxes & fees
21 Sept - 22 Sept
🌷Steps to Siesta Beach, Chic Studio, Pool & Patio

11. 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.
The price is £276
includes taxes & fees
21 Sept - 22 Sept
Siesta Key Village-Suite #1: A block to the Beach!

12. Fully renovated Siesta Key Condo | Walk to Beach | Pool | Perfect Location in SK Village

Fully renovated Siesta Key Condo | Walk to Beach | Pool | Perfect Location in SK Village
Siesta Key Village
9.4 out of 10, Exceptional, (92 reviews)
"This property was very comfortable for our family of 3, everything was very clean, specially the towels and bed sheets, has perfect location, walking distance to the beach and the village which is lovely with plenty of restaurants, few ice cream shops, nice cafes, we had a great time staying in this apartment and will definitely recommend to family and friends"
United States
Maliuska R.
Fully renovated Siesta Key Condo | Walk to Beach | Pool | Perfect Location in SK Village

13. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (42 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 £202
includes taxes & fees
24 Sept - 25 Sept
[Beach Elements] pool view withprivate beach access

14. Sea Escape - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Escape - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Siesta Key Village
10.0 out of 10, Exceptional, (25 reviews)
"Nice little spot that very close to the beach and everything else in the village. You can just park and not have to get in your vehicle the entire stay."
United States
Michael J.
The price is £486
includes taxes & fees
26 Sept - 27 Sept
Sea Escape - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

15. 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, (144 reviews)
"Accommodations were perfect for our family of 6. Extremely convenient to have private beach access along with chairs and ability to get umbrellas for shade."
United States
James N.
The price is £596
includes taxes & fees
21 Sept - 22 Sept
House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

16. Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
Siesta Key
9.6 out of 10, Exceptional, (68 reviews)
"We enjoyed the space this property offered our party of 6. We also appreciated the beach side location and proximity to restaurants and shops. We would stay here again."
United States
Meredith S.
The price is £490
includes taxes & fees
20 Sept - 21 Sept
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

17. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (191 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is £322
includes taxes & fees
22 Sept - 23 Sept
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

18. The Beach Club at Siesta Key #106D Resort by RVA

The Beach Club at Siesta Key #106D Resort by RVA
South Village
9.4 out of 10, Exceptional, (63 reviews)
"Everything was great. It was a good location to the beach."
United States
Angela A.
The price is £346
includes taxes & fees
21 Sept - 22 Sept
The Beach Club at Siesta Key #106D Resort by RVA

19. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
9.0 out of 10, Wonderful, (81 reviews)
"Good"
United States
Gelsy
The price is £339
includes taxes & fees
21 Sept - 22 Sept
2BR Beach Style w Pool Beach Club Siesta 204C RVA

20. Siesta Cooler: Only Minutes Walk to Siesta Beach!

Siesta Cooler: Only Minutes Walk to Siesta Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (75 reviews)
"great location- clean "
United States
Jon W.
The price is £287
includes taxes & fees
23 Sept - 24 Sept
Siesta Cooler: Only Minutes Walk to Siesta Beach!
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 £133 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 Siesta Heron Suites & Villas.

How many holiday rentals are there in Siesta Key?

With 406 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 Shell Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jim Neville Marine Preserve. While here, Crescent Beach and Safe Harbor Siesta Key are other places worth a visit.

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.