Siesta Key Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Siesta Key

Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas
Tropical Beach Resorts

Tropical Beach Resorts

3.5 star property
South Village
9.4 out of 10, Exceptional, (5096)
"The room was clean and the staff was very nice."
United States
Jill
The price is HK$1,116
HK$1,437 total
includes taxes & fees
17 Nov - 18 Nov
Tropical Beach Resorts
Front of property – evening/night
Captiva Beach Resort

Captiva Beach Resort

3.0 star property
South Village
9.0 out of 10, Wonderful, (1156)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
Captiva Beach Resort
Living area
SeaSpray Resort

SeaSpray Resort

4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (66)
"Pleasant stay, walk to beach and the Village. Good size mini apartment "
United States
Lisa L
The price is HK$1,857
HK$2,099 total
includes taxes & fees
17 Nov - 18 Nov
SeaSpray Resort
Front of property
The Ringling Beach House

The Ringling Beach House

3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (335)
"Clean, friendly and beach!"
United States
Mary
The Ringling Beach House
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
South Village
9.6 out of 10, Exceptional, (294)
"Fun place to stay for family vacation "
United States
Todd
The price is HK$2,636
HK$3,373 total
includes taxes & fees
8 Dec - 9 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club
Pool
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

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

Siesta Key Village
9.8 out of 10, Exceptional, (24)
"The check in and kitchen environment was great no complaints "
United States
nicholas c.
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
Exterior
Siesta Key Island Rentals

Siesta Key Island Rentals

3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (49)
"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
Garden
Siesta Palms By the Beach

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
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Inn On Siesta Key

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (189)
"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 HK$1,429
HK$2,046 total
includes taxes & fees
19 Nov - 20 Nov
The Inn On Siesta Key
Outdoor pool, a heated pool
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

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

Siesta Key Village
10.0 out of 10, Exceptional, (40)
"Very clean, new, close to downtown and the beach as well. Pool was the nicest we’ve seen, and the entire downstairs became a hangout all week for both kids and adults. Service from property manager Sarah was top notch!"
United States
Pete D.
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views
On the beach
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Siesta Key
9.6 out of 10, Exceptional, (27)
"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
Sun-loungers, beach towels
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

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

Siesta Key
10.0 out of 10, Exceptional, (13)
"Had a great time with great accommodations"
United States
Henry P.
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
On the beach
Private Home Directly on Siesta Key Beach!

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!
On the beach, sun-loungers, beach towels
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

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 HK$3,870
HK$8,058 total
includes taxes & fees
16 Nov - 17 Nov
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
On the beach, sun-loungers
Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views

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
Private kitchen
Siesta Heron Suites & Villas

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
Siesta Heron Suites & Villas
A heated pool
Home Steps from Siesta Key Beach and Village with Waterslide! On The Rocks

Home Steps from Siesta Key Beach and Village with Waterslide! On The Rocks

Siesta Key Village
9.8 out of 10, Exceptional, (45)
"Great house to stay with a large family. Close to the beach, shops, and restaurants."
United States
Aleasha B.
Home Steps from Siesta Key Beach and Village with Waterslide! On The Rocks
A heated pool
Jamaica Royale Siesta Key Condo 109

Jamaica Royale Siesta Key Condo 109

Siesta Key
9.2 out of 10, Wonderful, (23)
"8 minute walk to in my favorite beach. Easy to communicate with Michelle, she responded immediately to a question I had. Everything as posted on VRBO. Pool perfect temperature!"
United States
Larry B.
Jamaica Royale Siesta Key Condo 109
Outdoor pool, a heated pool
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!

Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!

Siesta Key
9.6 out of 10, Exceptional, (8)
"We loved this house. We celebrated a cousins 50th birthday and had so much fun. The location is close to all restaurants and beach. The golf cart was so fun to use. The house is nicely stocked with necessary items, pool noodles and toys. There was everything needed for the beach.The most important part was the owners were very responsive to all questions. We look forward to coming and staying here again."
United States
Nina D.
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!
On the beach, sun-loungers, beach towels
5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING

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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Siesta Key Hotel Reviews

The Inn On Siesta Key

The Inn On Siesta Key

10/10 Excellent
"Room was great!!! Staffa n owner awesome!!!"
Ronald 5-night trip
Posted 5 days ago
The Inn On Siesta Key

Find out more about Siesta Key

Search for holiday rentals in Siesta Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Siesta Key using one of the methods below:

  • View our selection of featured holiday rentals in Siesta Key
  • Use the map to find apartments and other holiday homes in the Siesta Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Siesta Key while they last

Look no further and take a look at our great range of rental properties in Siesta Key!

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 Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times and Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village.

How many holiday rentals are there in Siesta Key?

With 815 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.