Siesta Key Holiday Rentals

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Our top choices for Siesta Key holiday rentals

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 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 AU$437
includes taxes & fees
25 May - 26 May
[escape to paradise] siesta key beach getaway

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)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is AU$508
includes taxes & fees
25 May - 26 May
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (67 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
The price is AU$530
includes taxes & fees
25 May - 26 May
Siesta Key Island Rentals

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$654
includes taxes & fees
25 May - 26 May
Coastal Breeze Siesta - Turtle

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (129 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
The price is AU$462
includes taxes & fees
8 June - 9 June
SeaSpray Resort

Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool

Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool
Siesta Key
8.4 out of 10, Very good, (21 reviews)
"This was a fabulous location once we discovered the Trolley. The stop is right at the end of the road, we came during spring break and the traffic/ parking was horrific, so the Trolly was a lifesaver. The place was VERY clean and setting is awesome. I saw some reviews about the beds being soft, We actually slept better here than on our harder mattresses at home. I would definitely come back!"
United States
Carol
The price is AU$470
includes taxes & fees
31 May - 1 June
Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (198 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 AU$524
includes taxes & fees
25 May - 26 May
The Inn On Siesta Key

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, (75 reviews)
"Great location!!!! The condo was perfect for a couple and in a prime location. A very short walk to the beach and all the dining and shopping Siesta Key has to offer. The beach chairs and umbrella were a plus."
United States
Christina C.
The price is AU$567
includes taxes & fees
25 May - 26 May
Siesta Key Village-Suite #3: A Block to the Beach!

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$537
includes taxes & fees
26 May - 27 May
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Newly Renovated Beach-Side villa | Pool | Dock

Newly Renovated Beach-Side villa | Pool | Dock
Siesta Key Village
9.4 out of 10, Exceptional, (16 reviews)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is AU$578
includes taxes & fees
29 May - 30 May
Newly Renovated Beach-Side villa | Pool | Dock

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 AU$471
includes taxes & fees
26 May - 27 May
Siesta Heron Suites & Villas

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (30 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 AU$513
includes taxes & fees
28 May - 29 May
[Beach Elements] pool view withprivate beach access

Perfect Location minutes to beach and downtown with heated pool and hot tub

Perfect Location minutes to beach and downtown with heated pool and hot tub
Sarasota
9.8 out of 10, Exceptional, (8 reviews)
"Host was great! Location excellent! I would definitely stay again! "
United States
Laurie G.
The price is AU$449
includes taxes & fees
27 May - 28 May
Perfect Location minutes to beach and downtown with heated pool and hot tub

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,257 reviews)
"Great spot, short walk to the beach. Perfect for a couples weekend getaway."
United States
Cody
The price is AU$350
includes taxes & fees
25 May - 26 May
Captiva Beach Resort

Waterfront Siesta key entire King suite

Waterfront Siesta key entire King suite
Bay Isle
10.0 out of 10, Exceptional, (10 reviews)
The price is AU$406
includes taxes & fees
28 May - 29 May
Waterfront Siesta key entire King suite

Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear

Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear
Sarasota
9.8 out of 10, Exceptional, (17 reviews)
"Wonderful location Perfect for what we wanted in a quick escape. "
United States
Antonio
The price is AU$774
includes taxes & fees
25 May - 26 May
Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear

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, (115 reviews)
"Very clean and beautifully appointed "
United States
Monty H.
The price is AU$640
includes taxes & fees
5 June - 6 June
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Siesta Key
9.2 out of 10, Wonderful, (37 reviews)
"Very nice, clean and quiet place."
United States
Monika Z.
The price is AU$735
includes taxes & fees
26 May - 27 May
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

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, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is AU$425
includes taxes & fees
10 June - 11 June
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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, (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 AU$789
includes taxes & fees
31 May - 1 June
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ
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$326 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-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport and Last Minute Luxury Beachside Home 100 ft Walk to Siesta Key Beach Pool.

How many holiday rentals are there in Siesta Key?

With 408 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. You’ll find favourite places to visit such as Lido Beach and Venice Beach 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.