Siesta Key Holiday Rentals

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Holiday Rentals in Siesta Key

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4544)
"This property sustained significant damage from the hurricanes but they are expeditiously making all necessary repairs and improvements. The property is probably absolutely beautiful when the foliage and landscaping is in tact. The pathway from our specialty sun deck second-floor unit was a quick super short walk to the magnificent beach. On-site, office staff is very, very friendly and accommodating. The studio was adorable and tastefully decorated ~ appeared to be new and excellent condition....
The price is AU$501
includes taxes & fees
5 Feb - 6 Feb
Tropical Beach Resorts

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (226)
"I booked at the resort because we wanted a 2 1/2 bath unit. Unfortunately we got a 3 bedroom / 2 bath unit. I also wanted to trade up my unit to a2 bedroom ocean front because the resort was showing availability and management denied me the opportunity to pay for the upgrade. "
The price is AU$1,565
includes taxes & fees
19 Feb - 20 Feb
The Residences at Siesta Key Beach by Hyatt Vacation Club

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1068)
"Wonderful, everyone was very nice and helpful."
The price is AU$560
includes taxes & fees
2 Feb - 3 Feb
Captiva Beach Resort

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (288)
"Was only there for one night but it was comfortable and decent. The property was under construction at the time so it was a bit of a mess around the outside. The inside was not the cleanest I have ever seen but it was not too bad."
The Ringling Beach House

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"I love this property and people that run it are awesome. Paige you never left me hanging on anything you always answered my questions or problems immediately. Thank You"
Siesta Key Island Rentals

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (170)
"Wonderful stay on maybe the coldest weekend in Florida history. We were worried about if there was even heat... When we walked into our room we were pleased to feel they turned the heat on for us! Great communication and awesome location. "
The price is AU$1,123
includes taxes & fees
28 Feb - 1 Mar
The Inn On Siesta Key

Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

10.0 out of 10, Exceptional, (38)
"We had 16 of us staying at the property for a weekend birthday celebration (adult only). The property was amazing. Great location, walkable to everything. Very modern, new, clean and loved that all the bedrooms had their own bathroom. Pool area was great to hang out during the day, TV's outside to watch football games. Questions we had were immediately answered. Would definitely recommend and hoping to be back again someday!"
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B

8.6 out of 10, Excellent, (35)
"We loved our stay in this lovely little beach rental. The location was absolutely perfect for what we wanted - mere steps to the beach and an easy 20-minute walk to Siesta Key village. The rental seemed brand new- everything was clean and in perfect condition. We had everything we needed to enjoy a 4-night stay from towels to beach chairs to an umbrella, comfortable beds, and even a nespresso machine! Communication with the host was effortless and they made us feel welcomed, answering questions...
SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B

Amazing view of the Gulf!! Siesta Key at its best.

Amazing view of the Gulf!! Siesta Key at its best.

WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US

10.0 out of 10, Exceptional, (116)
"Very nice. Clean "
WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (28)
"This place was great I highly recommend it . The bed was hard and not comfortable and the couch was not very comfortable but the location and cleanliness of this place was great . We would definitely come back and stay . "
The price is AU$947
includes taxes & fees
24 Feb - 25 Feb
Siesta Heron Suites & Villas

Casa Blanca Villa D08

9.4 out of 10, Exceptional, (16)
"Everything were perfect"
Casa Blanca Villa D08

Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool

9.0 out of 10, Wonderful, (11)
"Hurricane Helene came before we did, so we are glad we stayed above carport. The AC was wonderful due to high humidity but they need to also run a dehumidifier in the apartment because all our clothes smelled musty. Kitchen was nice to have. Bed was fine. Shower was strong and clean. Extra blankets could have been cleaner. "
The price is AU$508
includes taxes & fees
4 Feb - 5 Feb
Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool

Luxury Home w/ Heated Pool and Private Beach Access

9.2 out of 10, Wonderful, (95)
"Very nice and spacious. Furniture in sitting areas definitely need to be replaced tho."
Luxury Home w/ Heated Pool and Private Beach Access

SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

9.8 out of 10, Exceptional, (35)
"Beautiful place. Lots of space. Excellent views comfortable furniture. "
The price is AU$1,792
includes taxes & fees
2 Feb - 3 Feb
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Beachfront Luxury Renovated Condo Directly On the Gulf

9.8 out of 10, Exceptional, (177)
"This property was amazing!! It was very clean, well put together, everything we needed was available! Gary was very responsive and pays attention to detail. The beds were very comfortable and the carpet was amazing!! The instructions were the best I’ve ever seen. We didn’t have any issues with getting beach chairs but it was off season. Loved the short walk to stores, restaurants and bars. We will rent from Gary again!!"
Beachfront Luxury Renovated Condo Directly On the Gulf

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

10.0 out of 10, Exceptional, (17)
"We had 5 couples and this house was perfect. House was beautiful and plenty of space....we never felt on top of each other. The backyard was such a great place to hang out after the beach. Unfortunately, we were booked Sat-Fri and on Tuesday night received the message we needed to evacuate due to the hurricane. Obviously, that killed our Tuesday night, and we were up and on the road Wednesday morning at 6am! Until then we had a perfect quick trip but had to head inland and find another rental....
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

9.6 out of 10, Exceptional, (85)
"Over all great, just never got a response on if the pool was heated or not"
The price is AU$890
includes taxes & fees
10 Feb - 11 Feb
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course

10.0 out of 10, Exceptional, (38)
"The property was perfect. We had six couples staying together for a special occasion in the Sarasota area.The common areas are perfect for gathering and the private bedroom/baths gave everyone some personal space.This is the second time we stayed in this space and we'll be back."
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course

Stunning Siesta Key,, . Reduced 2025, HEATED POOL, Book now HURRICANE SAFE

9.8 out of 10, Exceptional, (104)
"This is a nice vacation home close to Siesta Key beach."
Stunning Siesta Key,, . Reduced 2025, HEATED POOL, Book now HURRICANE SAFE
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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Other types of properties in Siesta Key you may be interested in

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4544)
"This property sustained significant damage from the hurricanes but they are expeditiously making all necessary repairs and improvements. The property is probably absolutely beautiful when the foliage and landscaping is in tact. The pathway from our specialty sun deck second-floor unit was a quick super short walk to the magnificent beach. On-site, office staff is very, very friendly and accommodating. The studio was adorable and tastefully decorated ~ appeared to be new and excellent condition....
The price is AU$501
includes taxes & fees
5 Feb - 6 Feb
Tropical Beach Resorts

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (226)
"I booked at the resort because we wanted a 2 1/2 bath unit. Unfortunately we got a 3 bedroom / 2 bath unit. I also wanted to trade up my unit to a2 bedroom ocean front because the resort was showing availability and management denied me the opportunity to pay for the upgrade. "
The price is AU$1,565
includes taxes & fees
19 Feb - 20 Feb
The Residences at Siesta Key Beach by Hyatt Vacation Club

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1068)
"Wonderful, everyone was very nice and helpful."
The price is AU$560
includes taxes & fees
2 Feb - 3 Feb
Captiva Beach Resort
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.

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 LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕. and SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B.

How many holiday rentals are there in Siesta Key?

With 799 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. 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.