Siesta Key Holiday Rentals

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Find properties with these dates

Tonight
May 14 - May 15
Tomorrow
May 15 - May 16
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

Holiday Rentals in Siesta Key

Property amenity
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4339)
"We had a lovely stay in the Specialty Sundeck Room, and we are already planning to return next year! The staff at the resort were so friendly, the room itself was perfect and comfortable, and the beach was beautiful. We rented a car, but honestly could have been fine without it since there were so many dining options so close by. Seriously could not have asked for a more perfect trip. Highly recommend! "
The price is HK$1,136
per night
22 May - 23 May
Tropical Beach Resorts
Sports facility
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (158)
"From the time we arrived we were treated kindly with great overall service. The entire staff makes you feel welcome and happy you are there. Overall great stay!"
The price is HK$3,797
per night
12 Jun - 13 Jun
The Residences at Siesta Key Beach by Hyatt Vacation Club
Private kitchen
Captiva Beach Resort
2.0 star property
9.0 out of 10, Wonderful, (1035)
"Everyone in the office is great and helpful right down to the cleaning staff! Especially Jen in the office. She is over the top accommodating. Wonderful customer service!! Couldn’t be happier here at our stay! The beach access is just a short walk with beautiful powdery sands and clear blue waters! Highly recommend!"
The price is HK$1,401
per night
20 May - 21 May
Captiva Beach Resort
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Aerial view
The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (239)
"Fantastic stay, such a great location, across from the beach access and a short walk to restaurants. Well stocked, cute and clean. Would definitely stay again! "
The price is HK$1,902
per night
19 May - 20 May
The Ringling Beach House
Beach
SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B
8.8 out of 10, Excellent, (26)
"We rented this house based upon the photos showing the vintage style beach home and because the location was literally steps away from where we were getting married on the beach. We had a minor mishap during our stay that was completely our fault. The owner was very responsive and understanding. I highly recommend this beautiful beach cottage."
SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B
Beach nearby
Beach Getaway Steps from the Sand w/ Shared Pool, Fast WiFi & Parking
8.8 out of 10, Excellent, (42)
"Conveniently located close to beach and village. However the area did get busy with public beach access nearby. Cute pool with outdoor shower but was also used by local kids. Unfortunately pest control treatment was scheduled during our stay and the guests upstairs had a domestic incident. But don’t let any of this deter you from booking. That was just our experience. The unit was perfect for a long weekend stay. Cleaning and maintenance people were very helpful and pleasant"
Beach Getaway Steps from the Sand w/ Shared Pool, Fast WiFi & Parking
Beach nearby
Beach Cottage Steps to Siesta Beach and Siesta Village Shops and Restaurants
8.0 out of 10, Very good, (22)
"This is a great place to stay for a couple; the house is small but cozy. We really enjoyed our stay, and would consider staying here again. This is more like a 4.5 star rating. There were a few things that kept this from being a 5 star review: bathroom shower was incredibly small. Also the towel rack needed to be screwed in tighter, it was starting to come off the wall. Bathroom could also use a new paint job. The coffeemaker likely needs replacing..the inside of the reservoir looked pretty bad....
The price is HK$860
per night
19 May - 20 May
Beach Cottage Steps to Siesta Beach and Siesta Village Shops and Restaurants
Room amenity
Siesta Key Island Rentals
3.0 star property
10.0 out of 10, Exceptional, (12)
"15 minute or less walk to everything you need. "
Siesta Key Island Rentals
Beach nearby, white sand, sun-loungers, beach umbrellas
Siesta Palms By the Beach
3.5 star property
9.2 out of 10, Wonderful, (93)
"Loved the beach feel. "
Siesta Palms By the Beach
Outdoor pool, a heated pool
2 BR/2 BA Condo on Siesta Key
9.8 out of 10, Exceptional, (17)
"Such a wonderful time! Quick walk to the beach! Trolly transportation was amazing!!"
2 BR/2 BA Condo on Siesta Key
On the beach, sun-loungers, beach towels
Super clean comfortable Modern Townhouse, Steps From PRIVATE Beach. 3 night min
9.8 out of 10, Exceptional, (189)
"We really enjoyed our stay. We were so close to the beach, it being private was great. Chairs are available to bring down on the beach but you don’t have to bring them back which was awesome. Great communication. Would definitely stay again."
Super clean comfortable Modern Townhouse, Steps From PRIVATE Beach. 3 night min
Beach
Siesta Key Beach House...................steps to main beach!!
Siesta Key Beach House...................steps to main beach!!
Beach nearby
SIESTA KEY BEACH , ROMANTIC UNIT C
9.0 out of 10, Wonderful, (17)
"Perfect location with a quick walk to the beach. Very clean, updated property. Excellent service. "
SIESTA KEY BEACH , ROMANTIC UNIT C
Fridge, microwave, oven, stovetop
Siesta Key Studio - on the BEACH!
10.0 out of 10, Exceptional, (34)
"my friend and I were looking for a relaxing week right by siesta beach, and this place made it all possible. the hosts were incredibly accommodating and there were so many items they provided that I wouldn’t have even thought to bring but we ended up needing. communication was excellent, and they are both so sweet! literally steps away from the beach and the pool was so lovely as well."
Siesta Key Studio - on the BEACH!
Beach nearby, sun-loungers, beach towels
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
9.6 out of 10, Exceptional, (98)
"My wife and I spent four days at the Gull. The location is excellent. Just around the corner and you are on the beach. Just one block walk and you are in Siesta Key old town eating and shopping. The air conditioning is a little different. Utilizing widow units and portable units. The portable unit’s exhaust air causing the bungalow to be in a huge negative. This causes a lot of hot attic air to be drawn in around the pocket door to the master bedroom. Overall we really enjoyed our stay and the...
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Beach nearby, sun-loungers, beach towels
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
9.2 out of 10, Wonderful, (39)
"Very clean place. Everything was provided. Close location to everything. My girlfriend and I had a great stay."
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
On the beach, sun-loungers, beach umbrellas, beach towels
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
9.8 out of 10, Exceptional, (118)
"Excellent vacation property right at the beautiful Siesta beach. We've rented both units, so we had the whole house and pool area all to ourselves. All details in the house are well though through, house is extremely clean and quiet. Large bedroms wth comfortable beds and plenty of common space in the front unit, smaller space in the back unit. Variety of food delivery options from restaurants in the area. The beach is short stroll away, my 82 yrs old mom was easily making the walk without her...
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
Property grounds
Luxury Home w/ Heated Pool and Private Beach Access
9.4 out of 10, Exceptional, (88)
"Our family stayed here and found it to be a very clean and well kept property. The private beach access was great. The pool gets very little sun, but still nice."
Luxury Home w/ Heated Pool and Private Beach Access
Private kitchen
Siesta Heron Suites & Villas
3.5 star property
8.4 out of 10, Very good, (26)
"I like everything, thank you so much!!!"
The price is HK$1,047
per night
15 May - 16 May
Siesta Heron Suites & Villas
Beach
Across The Street From #1 Beach
10.0 out of 10, Exceptional, (300)
"Right across the street from Beach 7 and only two blocks from all the shops and restaurants. The cottage was very nice, extremely clean (didn't see a single bug, which is rare in FL), and comfortable for the two of us. We made good use of the available beach chairs, umbrella, and bikes, and appreciated the outside shower to clean off after beach outings. Owner was very responsive. You'll need to take quarters for the laundry (we couldn't get the app to work). A bit of road noise, primarily on...
Across The Street From #1 Beach
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See all available properties in Siesta Key
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.

Other types of properties in Siesta Key you may be interested in

Outdoor pool, pool loungers
Siesta Key Beach Resort and Suites
2.5 star property
8.8 out of 10, Excellent, (1010)
"Beautiful, clean and convenient "
The price is HK$1,539
per night
27 May - 28 May
Siesta Key Beach Resort and Suites
Property amenity
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4339)
"We had a lovely stay in the Specialty Sundeck Room, and we are already planning to return next year! The staff at the resort were so friendly, the room itself was perfect and comfortable, and the beach was beautiful. We rented a car, but honestly could have been fine without it since there were so many dining options so close by. Seriously could not have asked for a more perfect trip. Highly recommend! "
The price is HK$1,136
per night
22 May - 23 May
Tropical Beach Resorts
Lobby sitting area
Tropical Breeze Resort
3.0 star property
9.0 out of 10, Wonderful, (1000)
"This is in a very good location as it is within walking distance of the beach and Main Street. It is steps away from the many restaurants and shopping in the area. The cottage was clean and cozy. The staff was very accommodating and helpful. I would definitely stay there again. "
The price is HK$2,184
per night
22 May - 23 May
Tropical Breeze 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 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 SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B.

How many holiday rentals are there in Siesta Key?

With 741 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.