Holiday Rentals in Siesta Key

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Holiday Rentals in Siesta Key

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, 4,369 reviews
"This resort was a great place to stay. Literally walking distance to a beautiful beach. Beach chairs and umbrellas available for purchase, beach towels provided free of charge. The kitchenette at this property was stocked with everything we needed. Room was clean and comfortable. Front office staff did a super quick check in. They have a movie dvd collection for in room entertainment. It would be awesome if the TVs were updated to have streaming apps such as Netflix. I would definitely return to...
The price is €163
per night
3 Jun - 4 Jun
Tropical Beach Resorts
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, 164 reviews
"The units are very spacious, clean and tastefully decorated. The pool is underwhelming as is the hot tub. Access to the beach was as advertised but losing the lounge chairs and umbrellas by 5:00 p.m.,hours before sunset is not ideal, especially for those with mobility issues who want to remain for the sunset, a highlight of the day. My children looked forward to paddle boarding and kayaking (as advertised) and inquired several times during our multiple day stay but were told none were available....
The price is €633
per night
19 Jun - 20 Jun
The Residences at Siesta Key Beach by Hyatt Vacation Club
The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, 248 reviews
"Excelence!!!! The property, the area, the beach and the property manager was out of standing!!! We are very very pleased!!"
The Ringling Beach House
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Captiva Beach Resort
2.0 star property
9.0 out of 10, Wonderful, 1,040 reviews
"Would recommend this place to others. Good price for so close to the Siesta Key Beach. "
The price is €202
per night
3 Jun - 4 Jun
Captiva Beach Resort
SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B
8.6 out of 10, Excellent, 27 reviews
"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 Getaway Steps from the Sand w/ Shared Pool, Fast WiFi & Parking
8.8 out of 10, Excellent, 42 reviews
"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 Cottage Steps to Siesta Beach and Siesta Village Shops and Restaurants
7.8 out of 10, Good, 23 reviews
"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 €490
per night
3 Jun - 4 Jun
Beach Cottage Steps to Siesta Beach and Siesta Village Shops and Restaurants
Siesta Palms By the Beach
3.5 star property
9.2 out of 10, Wonderful, 99 reviews
"Stayed at Siesta Palms by the Beach for a week in May. The unit we had was spacious and very clean. Plenty of towels for our week stay. The shower was awesome!! It was also nice to have beach amenities to take with us such as chairs, umbrella, cart. However, the chairs were pretty rusted and old. Could use an update. The area was quiet and serene. Located in a quiet neighborhood and very close to beach access. However, once you reach the beach there isnt a lot of space for people to spread out...
Siesta Palms By the Beach
2 BR/2 BA Condo on Siesta Key
9.8 out of 10, Exceptional, 19 reviews
"Really enjoyed our stay. Condo was spacious and grounds were beautiful! Pool was awesome as well!"
2 BR/2 BA Condo on Siesta Key
SIESTA KEY BEACH , ROMANTIC UNIT C
9.0 out of 10, Wonderful, 17 reviews
"Perfect location with a quick walk to the beach. Very clean, updated property. Excellent service. "
SIESTA KEY BEACH , ROMANTIC UNIT C
Super clean comfortable Modern Townhouse, Steps From PRIVATE Beach. 3 night min
9.8 out of 10, Exceptional, 190 reviews
"Steps to the beach, didn’t need our cars the entire time as there are free or for tip shuttles right off the main road always driving by. The village was extremely close only a 7min trolley ride. Home, bathrooms and beds were very clean. 3 full baths but showers were a bit tight for adults. Renter was very responsive and left some good tips in her book. Only real two small cons was the dryer was broken so we had to hang dry our laundry, and beach umbrella was missing a small piece which made it...
The price is €751
per night
17 Jun - 18 Jun
Super clean comfortable Modern Townhouse, Steps From PRIVATE Beach. 3 night min
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
9.8 out of 10, Exceptional, 118 reviews
"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...
The price is €2,803
per night
16 Jun - 17 Jun
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
Siesta Key Studio - on the BEACH!
10.0 out of 10, Exceptional, 35 reviews
"This spot was all as advertised. I was very impressed with this spot. The Murphy bed was better than expected and the keyless entry was perfect. :) Jim"
Siesta Key Studio - on the BEACH!
Siesta Key Beach House...................steps to main beach!!
Siesta Key Beach House...................steps to main beach!!
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
9.6 out of 10, Exceptional, 100 reviews
"This cottage is just steps away from the beach and Siesta Village with many restaurants, shops, and the market. You can park your car and never move it until check out. The cottage’s terrace was perfect for morning and nights. Everything was clean and neat. They have beach chairs (5 Tommy Bahama chairs), a cooler, beach cart, umbrella, and more. Keurig and drip coffee, everything we needed for the kitchen and plenty of paper supplies. We would definitely stay again."
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Luxury Home w/ Heated Pool and Private Beach Access
9.4 out of 10, Exceptional, 88 reviews
"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
Siesta Heron Suites & Villas
3.5 star property
8.4 out of 10, Very good, 26 reviews
"I like everything, thank you so much!!!"
The price is €376
per night
3 Jun - 4 Jun
Siesta Heron Suites & Villas
Surfs Up on Siesta Beach, Beachside Condo
9.2 out of 10, Wonderful, 52 reviews
"We had six guests that stayed at the place with a one year old. 5 nights. I paid extra to have the pack and play and highchair. The check in day our flight got delayed by 3hrs so we got in much later then expected. part of our group arrived and noticed us that those items wasnt there. I called and informed them and they brought the pack and play and highchair before we even got to the property. The next day we realized the highchair tray didn't match the highchair we had. Anyone who has a 1 yr...
Surfs Up on Siesta Beach, Beachside Condo
Across The Street From #1 Beach
10.0 out of 10, Exceptional, 303 reviews
"This is the perfect cottage for a couple’s getaway! It was one of the cleanest places we’ve ever rented. It is so tastefully decorated and had everything we needed for our stay. It’s right across from the beach access and only a 4 minute walk to Siesta Key village. There were also bikes available at the cottage which we used every day. Dave was a great host and we highly recommend staying at this cottage. We can’t wait to go back!"
Across The Street From #1 Beach
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course
10.0 out of 10, Exceptional, 30 reviews
"This home was perfect! Right across the street from the beach, large enough for our family of 6 and friends to stay, beautifully decorated, comfortable to hang out both inside and in the pool area. The owners thought of everything to make this home comfortable for guests. I would highly recommend this home and will definitely be returning."
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course
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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

Siesta Key Beach Resort and Suites
2.5 star property
8.6 out of 10, Excellent, 1,012 reviews
"This resort is absolutely perfect for a family beach vacation. We go every year. Thinking of starting to go twice a year. Already miss the resort and all the Siesta Key delights. 😊"
The price is €205
per night
3 Jun - 4 Jun
Siesta Key Beach Resort and Suites
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, 4,369 reviews
"This resort was a great place to stay. Literally walking distance to a beautiful beach. Beach chairs and umbrellas available for purchase, beach towels provided free of charge. The kitchenette at this property was stocked with everything we needed. Room was clean and comfortable. Front office staff did a super quick check in. They have a movie dvd collection for in room entertainment. It would be awesome if the TVs were updated to have streaming apps such as Netflix. I would definitely return to...
The price is €163
per night
3 Jun - 4 Jun
Tropical Beach Resorts
Tropical Breeze Resort
3.0 star property
9.0 out of 10, Wonderful, 1,005 reviews
"This was a great getaway for memorial day weekend. Booked this hotel last minute and it was wonderful! Staff was very friendly and accommodating. Room was great nice to have a kitchen Location was perfect Just a quick walk to the beach right down the street, Didn’t have the move the car and all the shops and restaurants are Also write down the street. Would definitely go back and stay again!! "
The price is €401
per night
9 Jun - 10 Jun
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.

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 €163 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 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.

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