Siesta Key Holiday Rentals

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Our top choices for Siesta Key holiday rentals

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5200)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
The price is AU$275
includes taxes & fees
7 Jan - 8 Jan
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2226)
"Very nice place !"
United States
Ivette
The price is AU$421
includes taxes & fees
1 Feb - 2 Feb
Hibiscus Suites - Gateway to Siesta Key

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (55)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
The price is AU$466
includes taxes & fees
8 Jan - 9 Jan
Siesta Key Island Rentals

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (84)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is AU$456
includes taxes & fees
13 Jan - 14 Jan
SeaSpray Resort

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (22)
"Jayme was super helpful when needed with our stay "
United States
Gabby L.
The price is AU$371
includes taxes & fees
8 Jan - 9 Jan
[Beach Elements] pool view withprivate beach access

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (346)
"Enjoyable stay. "
United States
Lori
The price is AU$349
includes taxes & fees
10 Jan - 11 Jan
Tiny House Siesta

The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
2.0 star property
Sarasota
10.0 out of 10, Exceptional, (2)
"It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable."
United States
Jackeline R.
The price is AU$316
includes taxes & fees
8 Jan - 9 Jan
The Mermaid at Tiny House Siesta

Coastal Breeze Siesta - Turtle

Coastal Breeze Siesta - Turtle
2.0 star property
Siesta Key
10.0 out of 10, Exceptional, (1)
"Great little place to stay and enjoy the nearby beaches and restaurants! The communication was on point. We will be back "
United States
Jacob
The price is AU$624
includes taxes & fees
18 Jan - 19 Jan
Coastal Breeze Siesta - Turtle

[lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (27)
"The property was very clean and conveniently located ."
United States
David
[lounge like locals] walk to siesta beach +bikes

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
South Village
9.6 out of 10, Exceptional, (306)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is AU$761
includes taxes & fees
5 Feb - 6 Feb
The Residences at Siesta Key Beach by Hyatt Vacation Club

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, (81)
"Wonderful experience! It was perfect for a girls’ weekend which included me, my mother & my 12 yr old daughters. There was enough restaurants in walking distance, the beach was in walking distance and we appreciated the trolley and frog hopper to get to Turtle Beach for kayaking. "
United States
Michelle A.
The price is AU$451
includes taxes & fees
12 Jan - 13 Jan
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES
South Village
9.6 out of 10, Exceptional, (42)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
The price is AU$369
includes taxes & fees
7 Jan - 8 Jan
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

[Sunny in Siesta] king bed + walk to beach

[Sunny in Siesta] king bed + walk to beach
South Village
9.8 out of 10, Exceptional, (10)
"Amazing stay, very clean & convenient "
United States
Ellen
The price is AU$527
includes taxes & fees
11 Jan - 12 Jan
[Sunny in Siesta] king bed + walk to beach

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is AU$566
includes taxes & fees
8 Jan - 9 Jan
Siesta Heron Suites & Villas

Siesta Shores: Siesta Key Suite - Ground flr- King

Siesta Shores: Siesta Key Suite - Ground flr- King
Sarasota
8.0 out of 10, Very good, (4)
"We enjoyed our stay in this quiet neighborhood. With just a 4 to 5 minute drive to the main strip it was a perfect getaway. Walls are thin but with a sound machine or white noise from your phone you will hear nothing."
United States
A Positive Feel
The price is AU$440
includes taxes & fees
7 Jan - 8 Jan
Siesta Shores: Siesta Key Suite - Ground flr- King

Tiny House Yellow Lifeguard Stand- pet friendly

Tiny House Yellow Lifeguard Stand- pet friendly
Sarasota
9.6 out of 10, Exceptional, (45)
"It was absolutely perfect like the photos show. We had a wonderful time. "
United States
Tiffanie D.
The price is AU$332
includes taxes & fees
20 Jan - 21 Jan
Tiny House Yellow Lifeguard Stand- pet friendly

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
The price is AU$508
includes taxes & fees
11 Jan - 12 Jan
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Minorga in Siesta Key Village

Minorga in Siesta Key Village
3.5 star property
Siesta Key Village
10.0 out of 10, Exceptional, (1)
"The property was close to all the shops and restaurants. 10 minute walk to the beach . It was updated and clean . We asked for new beach chairs because the ones there were broken and they came immediately. very accommodating "
United States
Meryl
The price is AU$810
includes taxes & fees
9 Jan - 10 Jan
Minorga in Siesta Key Village

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)
"Clean and Cute! Good communication with Host."
United States
Anonymous traveller
The price is AU$372
includes taxes & fees
20 Jan - 21 Jan
Tiny Coral Oasis- beachy tiny house for your getaway

NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS

NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS
South Village
9.4 out of 10, Exceptional, (44)
"Beautiful place close to the beach’s and love it would stay here again "
United States
Steve D.
The price is AU$332
includes taxes & fees
7 Jan - 8 Jan
NEW POOL Walk to beach, 1 bed 1 bath SPECIALS DAILY WEEKLY SPECIALS
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, 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 favourite 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 depend 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 AU$275 per night. Entering your travel dates in the search wizard might find you 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. 

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 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. Some other top choices in Siesta Key are 3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport. and Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times.

How many holiday rentals are there in Siesta Key?

With 384 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 Crescent 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.