Holiday Rentals in Siesta Key

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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, (5166)
"Great place, easy beach access and property was beautiful. "
United States
Maria
The price is €157
includes taxes & fees
25 Dec - 26 Dec
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, (2217)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key

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, (301)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is €434
includes taxes & fees
22 Jan - 23 Jan 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club

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 €213
includes taxes & fees
3 Jan - 4 Jan 2026
Tiny House Siesta

[lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (25)
"The property was very clean and conveniently located ."
United States
David
The price is €243
includes taxes & fees
25 Dec - 26 Dec
[lounge like locals] walk to siesta beach +bikes

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (79)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
The price is €298
includes taxes & fees
24 Dec - 25 Dec
SeaSpray Resort

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 €219
includes taxes & fees
5 Jan - 6 Jan 2026
The Mermaid at Tiny House Siesta

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (346)
"great location, very clean, quiet"
United States
Joaquin
The Ringling Beach House

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, (64)
"Well maintained, great location. We really enjoyed tge time there. Definitely looking forward to more trips."
United States
Barry L.
The price is €268
includes taxes & fees
24 Dec - 25 Dec
Siesta Key Village-Suite #3: A Block to the Beach!

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1176)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort

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)
"We loved our stay at the Drift Inn. Very clean, just the right amount of room for 4, easy access to the beach and pool. The beds were very comfortable. The owner was very quick to respond to questions from beginning to end. We would stay here again."
United States
Kimberly P.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is €415
includes taxes & fees
28 Dec - 29 Dec
The Inn On Siesta Key

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 €351
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Heron Suites & Villas

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 €426
includes taxes & fees
24 Dec - 25 Dec
Minorga in Siesta Key Village

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 €282
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Aqua Oasis- Tiny House sleeps 4 & Pet friendly

Aqua Oasis- Tiny House sleeps 4 & Pet friendly
Sarasota
9.0 out of 10, Wonderful, (33)
"We enjoyed our stay at this property. Highly recommend giving this place a shot. we'll be back for sure if we visit the area."
United States
Jason V.
The price is €175
includes taxes & fees
4 Jan - 5 Jan 2026
Aqua Oasis- Tiny House sleeps 4 & Pet friendly

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, (41)
"Loved the pool and view!"
United States
Victoria P.
The price is €284
includes taxes & fees
3 Jan - 4 Jan 2026
POOL VIEW King bed Walk to beach Covered porch overlooks pool DAILY RATES

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 €184
includes taxes & fees
25 Dec - 26 Dec
Tiny Coral Oasis- beachy tiny house for your getaway

Siesta Key Village-Suite #4: A block to the Beach!

Siesta Key Village-Suite #4: A block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (35)
"Was close to everything restaurants, bars,shoping and the best beach. "
United States
Crystal B.
Siesta Key Village-Suite #4: A block to the Beach!

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Siesta Key
9.8 out of 10, Exceptional, (101)
"Great location and the private beach was so nice! "
United States
Ashley N.
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key 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 €157 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. 

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 Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village and 3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport..

How many holiday rentals are there in Siesta Key?

With 390 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. While here, Siesta Key Marina and Point of Rocks 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.