Holiday Rentals in Siesta Key

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Holiday Rentals in Siesta Key

Tropical Beach Resorts

3.5 star property
South Village
9.4 out of 10, Exceptional, (5080)
"Clean, comfortable, and friendly staff."
United States
John
The price is €160
includes taxes & fees
9 Nov - 10 Nov
Tropical Beach Resorts

Captiva Beach Resort

3.0 star property
South Village
9.0 out of 10, Wonderful, (1153)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
Captiva Beach Resort

SeaSpray Resort

4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (61)
"Pleasant stay, walk to beach and the Village. Good size mini apartment "
United States
Lisa L
The price is €234
includes taxes & fees
11 Nov - 12 Nov
SeaSpray Resort

The Ringling Beach House

3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (334)
"Clean, friendly and beach!"
United States
Mary
The Ringling Beach House

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
South Village
9.6 out of 10, Exceptional, (294)
"We celebrated my daughter’s 30th birthday and it was perfect. I can’t wait to stay again. The beach was truly amazing. This place has everything you need. "
United States
Tammy
The price is €449
includes taxes & fees
4 Dec - 5 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club

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

Siesta Key Village
9.8 out of 10, Exceptional, (24)
"Beatiful property, one block from the beach. Plenty of amenities"
United States
ervin m.
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

Siesta Key Island Rentals

3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (48)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
United States
Julianna
Siesta Key Island Rentals

Siesta Palms By the Beach

3.5 star property
South Village
9.4 out of 10, Exceptional, (136)
"Comfy and clean, nice and close to the beach. Pool was very clean. Quiet, safe area. Would highly recommend!"
United States
Lynn
Siesta Palms By the Beach

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (188)
"This property was great and it is a quick walk to the beach and village. The Cabana suited our family of four. We had enough space to spread out and relax. If we return to Siesta Key, we would stay here again."
United States
Brooke
The price is €260
includes taxes & fees
11 Nov - 12 Nov
The Inn On Siesta Key

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

Siesta Key Village
10.0 out of 10, Exceptional, (40)
"All around great experience - will be coming back to this area and booking another rental with this management company."
United States
Shaun T.
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Siesta Key
9.8 out of 10, Exceptional, (26)
"Everything is super clean and super good. The beach is super nice. The atmosphere is incredible."
United States
Yasiel G.
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

Siesta Key
10.0 out of 10, Exceptional, (12)
"Had a great time with great accommodations"
United States
Henry P.
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Siesta Key
9.6 out of 10, Exceptional, (55)
"We had a wonderful stay. This is truly a very short walk to the beach as well as to the Siesta Key restaurants and shops. We truly enjoyed our stay!"
United States
Anne W.
The price is €925
includes taxes & fees
16 Nov - 17 Nov
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views

Siesta Key
9.4 out of 10, Exceptional, (68)
"This is our second time staying here. Absolutely love this rental. Very clean and walking distance to the village "
United States
Curtis R.
Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views

Siesta Heron Suites & Villas

3.5 star property
Siesta Key
8.4 out of 10, Very good, (37)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is €305
includes taxes & fees
10 Nov - 11 Nov
Siesta Heron Suites & Villas

Private Home Directly on Siesta Key Beach!

Siesta Key
9.8 out of 10, Exceptional, (8)
"The home was beautiful and well equipped and management was quick to respond to any questions that we had. Direct access to a gorgeous beach was definitely the highlight!! "
United States
Brandi C.
Private Home Directly on Siesta Key Beach!

Waterfront Home, Pool, Waterslide, Games! - Siesta Serenity

South Village
9.6 out of 10, Exceptional, (9)
"The house definitely met all of our expectations "
United States
Karey B.
Waterfront Home, Pool, Waterslide, Games! - Siesta Serenity

Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!

Siesta Key
9.4 out of 10, Exceptional, (36)
"Great location and experience"
United States
Mayt M.
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!

Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Siesta Key Village
9.6 out of 10, Exceptional, (141)
"Perfect location! So easy to walk to the beach!"
United States
Melody W.
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING

Siesta Key
10.0 out of 10, Exceptional, (142)
"Very close to the beach, a short walk to the village, and plenty of common space for family gathering. "
United States
Andrea G.
5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING
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 €160 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 Heron Suites & Villas.

How many holiday rentals are there in Siesta Key?

With 809 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. While here, Siesta Key Marina and Point of Rocks are other places worth a visit.

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.