Siesta Key Holiday Rentals

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec
In four months
16 Jan - 18 Jan

Holiday Rentals in Siesta Key

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

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (5003)
"A great little hotel, the beach is beautiful too, will be back, this is our 3rd year coming."
The price is HK$1,085
HK$1,402 total
includes taxes & fees
28 Sept - 29 Sept
Tropical Beach Resorts
Captiva Beach Resort
Front of property – evening/night

Captiva Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (1140)
"2nd time and excellent as always..close to the beach and great surroundings "
The price is HK$1,171
HK$1,455 total
includes taxes & fees
27 Oct - 28 Oct
Captiva Beach Resort
SeaSpray Resort
Living area

SeaSpray Resort

4.0 star property
9.4 out of 10, Exceptional, (43)
"Our stay was beautiful this hotel. Staff were very great. Customer service was great."
The price is HK$1,604
HK$1,812 total
includes taxes & fees
28 Sept - 29 Sept
SeaSpray Resort
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (326)
"We liked the stay very much "
The Ringling Beach House
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
Pool

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

9.8 out of 10, Exceptional, (24)
"Beatiful property, one block from the beach. Plenty of amenities"
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
The Residences at Siesta Key Beach by Hyatt Vacation Club
Property amenity

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.6 out of 10, Exceptional, (290)
"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. "
The price is HK$3,342
HK$4,173 total
includes taxes & fees
9 Oct - 10 Oct
The Residences at Siesta Key Beach by Hyatt Vacation Club
Siesta Palms By the Beach
Garden

Siesta Palms By the Beach

3.5 star property
9.4 out of 10, Exceptional, (131)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach
Private Home Directly on Siesta Key Beach!
On the beach

Private Home Directly on Siesta Key Beach!

9.8 out of 10, Exceptional, (6)
Private Home Directly on Siesta Key Beach!
Siesta Key Island Rentals
Private kitchen

Siesta Key Island Rentals

3.0 star property
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. "
Siesta Key Island Rentals
The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The Inn On Siesta Key
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
On the beach

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (23)
"Everything is super clean and super good. The beach is super nice. The atmosphere is incredible."
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (40)
"This was the perfect place to stay for a large family with kids. The location to the beach and restaurants couldn't have been more convenient. Amazing vacation!"
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views
Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views
On the beach, sun-loungers

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

9.4 out of 10, Exceptional, (65)
"This is our second time staying here. Absolutely love this rental. Very clean and walking distance to the village "
Beachfront 3-Bedroom Condo on Siesta Key – Steps to the Sand & Gulf Views
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!
On the beach, sun-loungers

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

9.4 out of 10, Exceptional, (35)
"Great location and experience"
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!
Zach’s Siesta Key Beach House|Pet Friendly| #1 Beach in USA
3 bedrooms, desk, iron/ironing board, free WiFi

Zach’s Siesta Key Beach House|Pet Friendly| #1 Beach in USA

Zach’s Siesta Key Beach House|Pet Friendly| #1 Beach in USA
5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING
On the beach, sun-loungers, beach towels

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

10.0 out of 10, Exceptional, (141)
"This property was perfect for our family gathering. Enough space to sit and talk and the pool was wonderful. Plenty of beach chairs, toys, towels and beach buggies to enjoy a day at the beach. "
5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (47)
"Great place and people"
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course
Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West
A heated pool

Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West

9.6 out of 10, Exceptional, (61)
"Great location!"
The price is HK$2,179
HK$4,922 total
includes taxes & fees
29 Sept - 30 Sept
Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West
Siesta Beachfront Paradise: Luxurious Home Steps from Beach with Infinity Pool!
A heated pool

Siesta Beachfront Paradise: Luxurious Home Steps from Beach with Infinity Pool!

10.0 out of 10, Exceptional, (3)
"We loved the house! Great location, beautiful spaces, plenty of room for all of us. Couldn’t have picked a better place for our family to stay for our niece’s wedding! We’d definitely love to stay here again!"
Siesta Beachfront Paradise: Luxurious Home Steps from Beach with Infinity Pool!
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
On the beach, sun-loungers, beach towels

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

9.6 out of 10, Exceptional, (52)
"House was very nice. Was clean when we arrived. Plenty of space and beautiful view "
The price is HK$3,097
HK$7,074 total
includes taxes & fees
30 Sept - 1 Oct
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
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

Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"Beach was close as well as bars and restaurants "
Mike 5-night trip
Posted 4 days ago
Siesta Key Beach Resort and Suites

Find out more about 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
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  • 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 806 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.