Siesta Key Holiday Rentals

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Our top choices for Siesta Key holiday rentals

Beachy Sarasota Duplex

Beachy Sarasota Duplex
Sarasota
10.0 out of 10, Exceptional, (4 reviews)
"Great experience. House was in a great location and having a Dunkin walking distance was a plus. Definitely would recommend. Thank you A"
United States
pete t.
The price is AU$641
includes taxes & fees
12 Apr - 13 Apr
Beachy Sarasota Duplex

Sarasota Duplex near Siesta Key

Sarasota Duplex near Siesta Key
Sarasota
9.4 out of 10, Exceptional, (6 reviews)
"We enjoyed our stay! Location was great!!"
United States
Jacy N.
The price is AU$599
includes taxes & fees
5 May - 6 May
Sarasota Duplex near Siesta Key

Tiny House Calypso with 1st floor sleeping

Tiny House Calypso with 1st floor sleeping
Sarasota
9.0 out of 10, Wonderful, (10 reviews)
"Third time here and best visit will book again in future "
United States
Desirae
The price is AU$298
includes taxes & fees
8 Apr - 9 Apr
Tiny House Calypso with 1st floor sleeping

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
Unwind Poolside + Walk to Beach! Sarasota Retreat

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"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$546
includes taxes & fees
14 Apr - 15 Apr
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Beachside villa in Siesta Key | Canal Front | pool

Beachside villa in Siesta Key | Canal Front | pool
Siesta Key Village
9.8 out of 10, Exceptional, (19 reviews)
"Nice clean and a short walk to everything!"
United States
Ralph S.
The price is AU$609
includes taxes & fees
22 Apr - 23 Apr
Beachside villa in Siesta Key | Canal Front | pool

Modern beach Retreat | Canal view | Private dock

Modern beach Retreat | Canal view | 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 AU$720
includes taxes & fees
19 Apr - 20 Apr
Modern beach Retreat | Canal view | Private dock

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, (86 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is AU$441
includes taxes & fees
13 Apr - 14 Apr
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Turtle at Coastal Breeze | Peaceful 2nd Floor, Walk to Turtle Beach, On the Bay, Boat Dock, Fishing

Turtle at Coastal Breeze | Peaceful 2nd Floor, Walk to Turtle Beach, On the Bay, Boat Dock, Fishing
Sarasota
10.0 out of 10, Exceptional, (21 reviews)
"Will stay here again."
United States
Anonymous traveller
The price is AU$766
includes taxes & fees
9 Apr - 10 Apr
Turtle at Coastal Breeze | Peaceful 2nd Floor, Walk to Turtle Beach, On the Bay, Boat Dock, Fishing

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (41 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is AU$530
includes taxes & fees
28 Apr - 29 Apr
Siesta Heron Suites & Villas

The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
Sarasota
10.0 out of 10, Exceptional, (3 reviews)
"The inside was very clean, we were very impressed! Being only a few minutes away from the beach, the location was perfect for what we had in mind. Area was surrounded by places to go shop as well. Would definitely stay again!"
United States
Jaret
The price is AU$301
includes taxes & fees
13 Apr - 14 Apr
The Mermaid at Tiny House Siesta

Tiny House Green Lifeguard Stand - sleeps 5

Tiny House Green Lifeguard Stand - sleeps 5
Sarasota
9.4 out of 10, Exceptional, (29 reviews)
"It was a great fit for our family and we enjoyed the experience. "
United States
Stephanie H.
The price is AU$301
includes taxes & fees
12 Apr - 13 Apr
Tiny House Green Lifeguard Stand - sleeps 5

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ
Siesta Key Village
9.0 out of 10, Wonderful, (13 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 AU$876
includes taxes & fees
28 Apr - 29 Apr
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Coastal Breeze Siesta - Turtle

Coastal Breeze Siesta - Turtle
2.0 star property
Siesta Key
10.0 out of 10, Exceptional, (1 review)
"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$746
includes taxes & fees
9 Apr - 10 Apr
Coastal Breeze Siesta - Turtle

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (105 reviews)
"Perfect location, nice amenities for the beach, pet friendly, would stay here again! Super convenient and clean "
United States
Jayline
The price is AU$505
includes taxes & fees
3 May - 4 May
SeaSpray Resort

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 reviews)
"Cute tiny house Clean and comfortable Had a great time"
United States
DeAnna T.
The price is AU$296
includes taxes & fees
14 Apr - 15 Apr
Tiny Coral Oasis- beachy tiny house for your getaway

Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (47 reviews)
"Beautiful place close to the beach’s and love it would stay here again "
United States
Steve D.
The price is AU$391
includes taxes & fees
8 Apr - 9 Apr
Siesta Key, Sea Horse Villa, Pool. Daily rentals

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, (46 reviews)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
The price is AU$530
includes taxes & fees
13 Apr - 14 Apr
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

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, (85 reviews)
"106A was great - loved the sitting area right outside our door. Also loved that the beach chairs and umbrella were in a bedroom closet. Showers were great too. Will likely stay here again."
United States
Margaret
The price is AU$550
includes taxes & fees
13 Apr - 14 Apr
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Studio Retreat Across the Street from Beautiful Siesta Key Beach

Studio Retreat Across the Street from Beautiful Siesta Key Beach
Siesta Key
8.8 out of 10, Excellent, (158 reviews)
"Pristinely clean comfortable and very close to beach with free parking it was a great place to stay! Would recommend!"
United States
Stina
The price is AU$544
includes taxes & fees
12 Apr - 13 Apr
Studio Retreat Across the Street from Beautiful 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, 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$314 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 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. Some other top choices in Siesta Key are Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool and Gull Villa – Spacious 2BR, Walk to Siesta Key & Village, 1945 Triplex .

How many holiday rentals are there in Siesta Key?

With 392 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 Siesta Key Marina 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.