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

Siesta Key Holiday Rentals

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Our top choices for Siesta Key holiday rentals

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (72 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
Siesta Key Island Rentals

SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!

SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!
Siesta Key
9.4 out of 10, Exceptional, (31 reviews)
"Exactly as pictured, tucked away little beach bungalow just steps from the beach. VERY quiet despite it being spring break. Place was IMMACULATE and didn’t show any signs of wear and tear like other rentals can show. Would absolutely stay here again in a heart beat and recommend to other couples. "
United States
Kathryn H.
SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!

[lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (36 reviews)
"Only 10 mins walking from the Village, so easy to check in, great communication, super clean. "
United States
John
The price is AU$543
includes taxes & fees
16 July - 17 July
[lounge like locals] walk to siesta beach +bikes

Island Villa | Cozy Beach Retreat | Walk to Village

Island Villa | Cozy Beach Retreat | Walk to Village
Siesta Key Village
8.4 out of 10, Very good, (13 reviews)
The price is AU$665
includes taxes & fees
15 July - 16 July
Island Villa | Cozy Beach Retreat | Walk to Village

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,279 reviews)
"Great spot for a weekend getaway."
United States
Tom
The price is AU$293
includes taxes & fees
9 July - 10 July
Captiva Beach Resort

2 Bedroom 2 Bath home near Siesta Key Beach

2 Bedroom 2 Bath home near Siesta Key Beach
Sarasota
8.6 out of 10, Excellent, (40 reviews)
"Great little place -perfect for a few days in siesta "
United States
Linda K.
The price is AU$447
includes taxes & fees
16 July - 17 July
2 Bedroom 2 Bath home near Siesta Key Beach

Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
South Village
8.8 out of 10, Excellent, (88 reviews)
"First time here what a great place very close to everything "
United States
Elena B.
The price is AU$564
includes taxes & fees
13 July - 14 July
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
The Inn On Siesta Key

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

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

Bright & Beachy–Beach Club Siesta Key 100A by RVA

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (118 reviews)
"Convenient location - close to beach. Umbrella & beach chairs in closet came in handy. "
United States
Mary
The price is AU$494
includes taxes & fees
13 July - 14 July
Bright & Beachy–Beach Club Siesta Key 100A by RVA

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is AU$495
includes taxes & fees
9 July - 10 July
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, (34 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$417
includes taxes & fees
15 July - 16 July
[Beach Elements] pool view withprivate beach access

Dolphin Villa - Pool - Steps to Siesta Key Village

Dolphin Villa - Pool - Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"Great location to downtown, beach. Kitchen and furnishing updated and in great condition. Negatives would be the lock on the backdoor, air conditioning from the ceiling that could not be controlled from our apartment. The pool was great and had plenty of seating. Only issue with the Dolphin apartment is the many windows, which kind of made it feel like living in a fish bowl. That might not be an issues for others. "
United States
Sandra C.
The price is AU$508
includes taxes & fees
9 July - 10 July
Dolphin Villa - Pool - Steps to Siesta Key Village

Siesta Key Studio close to beaches, city, and airport.

Siesta Key Studio close to beaches, city, and airport.
Siesta Key
8.4 out of 10, Very good, (13 reviews)
"Fantastic experience, great host, and close to everything!"
United States
Shannon
The price is AU$328
includes taxes & fees
12 July - 13 July
Siesta Key Studio close to beaches, city, and airport.

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$281
includes taxes & fees
13 July - 14 July
Tiny Coral Oasis- beachy tiny house for your getaway

Sea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (22 reviews)
"Everything was close and way to get to and from beach,,, great place and Matt was very helpful!"
United States
Warren C.
The price is AU$937
includes taxes & fees
2 Aug - 3 Aug
Sea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
South Village
9.8 out of 10, Exceptional, (34 reviews)
"Private, nice, and new Easy access Would stay again "
United States
Frederick
The price is AU$434
includes taxes & fees
6 Aug - 7 Aug
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to 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$711
includes taxes & fees
4 Aug - 5 Aug
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Everglades Villa • Sleeps 8 • Walk to Siesta Beach

Everglades Villa • Sleeps 8 • Walk to Siesta Beach
Siesta Key Village
9.0 out of 10, Wonderful, (14 reviews)
"We loved staying here for my bachelorette!"
United States
Kelsey E.
The price is AU$779
includes taxes & fees
4 Aug - 5 Aug
Everglades Villa • Sleeps 8 • Walk to Siesta Beach

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, (89 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is AU$444
includes taxes & fees
2 Aug - 3 Aug
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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$293 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. 

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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 3 bed 2 Bath, heated pool, walk to beach and village.

How many holiday rentals are there in Siesta Key?

With 424 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 Siesta Key Beach Playground 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.