Holiday Rentals in Siesta Key

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Our top choices for Siesta Key holiday rentals

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
The price is €464
includes taxes & fees
25 Mar - 26 Mar
Unwind Poolside + Walk to Beach! Sarasota Retreat

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)
"Great location, clean, good communication. "
United States
Alexandra P.
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (29 reviews)
"Clean and great location! Would stay again! "
United States
Laura W.
The price is €305
includes taxes & fees
31 Mar - 1 Apr
[escape to paradise] siesta key beach getaway

Beachy Sarasota Duplex

Beachy Sarasota Duplex
Sarasota
10.0 out of 10, Exceptional, (3 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.
Beachy Sarasota Duplex

1 mile to Siesta Key! Early Bird Special & Low Wkly Rates! Heated Pool! BBQ

1 mile to Siesta Key! Early Bird Special & Low Wkly Rates! Heated Pool! BBQ
Sarasota
9.6 out of 10, Exceptional, (124 reviews)
"You are in your own piece of paradise when you stay here. Many amenities available. Ven, our host was always available when needed."
United States
Elizabeth D.
The price is €391
includes taxes & fees
25 Mar - 26 Mar
1 mile to Siesta Key! Early Bird Special & Low Wkly Rates! Heated Pool! BBQ

Siesta Cooler: Only Minutes Walk to Siesta Beach!

Siesta Cooler: Only Minutes Walk to Siesta Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (67 reviews)
"Host was great, clean room, balcony was nice. It’s on the Main Street so not quite until the bars closed. Overall a great place to visit. "
United States
Brandon N.
The price is €411
includes taxes & fees
31 Mar - 1 Apr
Siesta Cooler: Only Minutes Walk to Siesta Beach!

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)
"The room was very clean and close to everything. We had to buy toilet paper and Kleenex as there wasn’t enough for the room. Enjoyed our stay"
United States
Kelly F.
Beachside villa in Siesta Key | Canal Front | pool

· King bed . Pool. Daily rentals

· King bed . Pool. Daily rentals
South Village
9.8 out of 10, Exceptional, (32 reviews)
"Private, nice, and new Easy access Would stay again "
United States
Frederick
· King bed . Pool. Daily 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 €487
includes taxes & fees
1 Apr - 2 Apr
Coastal Breeze Siesta - Turtle

Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly

Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly
Siesta Key Village
9.8 out of 10, Exceptional, (77 reviews)
"This house was clean and in a perfect location within walking distance to the beach and the village. Perfect size for our family of 5 for a 2 night stay in November."
United States
Patrick G.
The price is €818
includes taxes & fees
25 Mar - 26 Mar
Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly

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, (20 reviews)
"The place was perfect for our 3 day getaway!"
United States
Amy
Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool

Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (45 reviews)
"The apartment is clean and comfortable! Location is amazing! The beach, restaurants, and bars are all very close. The beach is great and easily accessible. 100% would stay here again! "
United States
Alex
The price is €398
includes taxes & fees
30 Mar - 31 Mar
Siesta Key Village-Suite #1: A block to the Beach!

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (27 reviews)
"It had everything we needed. Comfortable bed. Great location. Easy wall to the beach "
United States
Noreen W.
The price is €353
includes taxes & fees
31 Mar - 1 Apr
[Beach Elements] pool view withprivate beach access

King bed. Pool. Daily rentals

King bed. Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (46 reviews)
"Beautiful place close to the beach’s and love it would stay here again "
United States
Steve D.
The price is €301
includes taxes & fees
13 Apr - 14 Apr
King bed. Pool. Daily rentals

Condo with Private Beach Access, Great Shared Amenities - Private Beach House

Condo with Private Beach Access, Great Shared Amenities - Private Beach House
Siesta Key
9.2 out of 10, Wonderful, (45 reviews)
"Very nice property! Beautiful beach! We had a problem with one of the showers and it was solved right away.The communication with the management was excellent , they reached to us several times though texts to make sure everything was ok.We highly recommend this property!"
United States
Fernanda L.
Condo with Private Beach Access, Great Shared Amenities - Private Beach House

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.
Sarasota Duplex near Siesta Key

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
9.6 out of 10, Exceptional, (15 reviews)
"We had a lovely week in this property and even saw some dolphins swimming by!"
United States
Hilda H.
The price is €570
includes taxes & fees
5 Apr - 6 Apr
Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear

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 €331
includes taxes & fees
14 Apr - 15 Apr
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (101 reviews)
"VERY ENJOYABLE /STAFF WAS EXCELLENT"
United States
KARL
The price is €369
includes taxes & fees
21 Apr - 22 Apr
SeaSpray Resort

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (64 reviews)
"We had a wonderful time-perfect location to beach and village. Was nice to come back to a very comfortable and relaxing home. Definitely recommend-5 stars! "
United States
Laura
The price is €433
includes taxes & fees
25 Mar - 26 Mar
Siesta Key Island Rentals
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 €178 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 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 Steps to Beach/Siesta Village-Resort Pool w/Slide.

How many holiday rentals are there in Siesta Key?

With 394 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 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.