Siesta Key Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Vacation Rentals in Siesta Key

Our top choices for Siesta Key vacation rentals

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, (4919)
"Wonderful resort "
The price is ￥20,555
￥26,558 total
includes taxes & fees
Sep 2 - Sep 3
Tropical Beach Resorts
SeaSpray Resort
Deluxe Suite, 2 Bedrooms | Living area

SeaSpray Resort

4.0 star property
9.4 out of 10, Exceptional, (25)
"Renovated resort, a block away from the beach, very clean and friendly staff. Would stay there again. "
The price is ￥30,817
￥34,823 total
includes taxes & fees
Sep 1 - Sep 2
SeaSpray Resort
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)
"The house was in great condition and near everything. "
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (319)
"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "
The Ringling Beach House
Captiva Beach Resort
Front of property - evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1124)
"Everything was great and a walking distance to the beach❤️❤️❤️❤️❤️. Everyone was very friendly and kind, thank you so much."
Captiva Beach Resort
Siesta Palms By the Beach
Garden

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (126)
"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!

10.0 out of 10, Exceptional, (3)
"Beautiful place to stay… direct walk to the beach from your back door. Amazing view! Clean with all the amenities you need. "
Private Home Directly on Siesta Key Beach!
Siesta Key Island Rentals
322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (46)
"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. "
The price is ￥22,768
￥47,881 total
includes taxes & fees
Sep 3 - Sep 4
Siesta Key Island Rentals
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
9.8 out of 10, Exceptional, (284)
"Great location. Everyone was very friendly and accommodating!"
The price is ￥63,198
￥78,926 total
includes taxes & fees
Sep 8 - Sep 9
The Residences at Siesta Key Beach by Hyatt Vacation Club
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 price is ￥34,616
￥47,296 total
includes taxes & fees
Aug 28 - Aug 29
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, (20)
"We had a great stay at this property! We had five adults and one infant with plenty of room to be comfortable. We enjoyed the short walk to the beach and that beach chairs were provided by the HOA (umbrellas are not but there was one at the property). The owners were wonderful, fast responses to any messages and made sure we had everything we needed to have a great time! Definitely recommend this property if you’re in Siesta Key and looking to be very close to the beach!"
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
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, (34)
"Great location and experience"
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!
Siesta Heron Suites & Villas
Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very Good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
The price is ￥28,674
￥85,554 total
includes taxes & fees
Aug 31 - Sep 1
Siesta Heron Suites & Villas
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
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (1)
"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."
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!
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!
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)
"This was an amazing house. It had everything you could want, walkable to everything, restaurant shopping , and the beach. We never needed to rent a car. So many things to do at this house. Every age range of people were completely satisfied. I would definitely stay at this house again it was beautiful top to bottom. "
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course
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, (64)
"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
5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING
On the beach, sun loungers, beach towels

5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT 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, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Beach nearby, sun loungers, beach towels

Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

9.6 out of 10, Exceptional, (109)
"Awesome location, perfect beach supplies provided, and VERY clean! "
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
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.
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

Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

10/10 Excellent
"Really nice hotel and great location. The staff was very friendly and helpful. "
Rexann 2-night trip
Posted 2 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
  • 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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Siesta Key?

Yes, we give you a choice of vacation rentals in Siesta Key close to Jim Neville Marine Preserve, or you can go with a more secluded option if you'd like a relaxing place to 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 vacation rentals in Siesta Key?

Siesta Key Island Rentals: Visitors give good reviews to this Siesta Key vacation home rental, which comes with free WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Siesta Key is Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times.

How many vacation rentals are there in Siesta Key?

With 809 Expedia vacation rentals, you're sure 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 vacation rentals like in Siesta Key?

Vacation rentals are private accommodations you can stay in for several days or longer in Siesta Key. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.