Siesta Key Vacation Rentals

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Vacation Rentals in Siesta Key

Our top choices for Siesta Key vacation rentals

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4985)
"A great little hotel, the beach is beautiful too, will be back, this is our 3rd year coming."
$159 nightly
The price is $180
Sep 17 - Sep 18
Total with taxes and fees
Tropical Beach Resorts

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1133)
"2nd time and excellent as always..close to the beach and great surroundings "
$153 nightly
The price is $171
Sep 28 - Sep 29
Total with taxes and fees
Captiva Beach Resort

SeaSpray Resort

4.0 star property
9.4 out of 10, Exceptional, (38)
"I love everything about this place so beautiful with walking distance to the beach "
$229 nightly
The price is $259
Sep 17 - Sep 18
Total with taxes and fees
SeaSpray Resort

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (324)
"We liked the stay very much "
The Ringling Beach House

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

3.5 star property
9.6 out of 10, Exceptional, (290)
"Great location. Everyone was very friendly and accommodating!"
$436 nightly
The price is $493
Sep 29 - Sep 30
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (128)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach

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. "
$234 nightly
The price is $265
Sep 17 - Sep 18
Total with taxes and fees
Siesta Key Island Rentals

Private Home Directly on Siesta Key Beach!

10.0 out of 10, Exceptional, (5)
Private Home Directly on Siesta Key Beach!

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

9.6 out of 10, Exceptional, (22)
"Everything is super clean and super good. The beach is super nice. The atmosphere is incredible."
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

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

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

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

9.6 out of 10, Exceptional, (51)
"House was very nice. Was clean when we arrived. Plenty of space and beautiful view "
$612 nightly
The price is $683
Sep 17 - Sep 18
Total with taxes and fees
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

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

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

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

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!

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!

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!

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!!"
$266 nightly
The price is $301
Sep 18 - Sep 19
Total with taxes and fees
Siesta Heron Suites & Villas
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

Price trends for vacation rentals in Siesta Key

Price trends for vacation rentals in Siesta Key

Less expensive
More expensive
Next month
August
March
$299
Month
Price
January
$337
February
$465
March
$479
April
$395
May
$324
June
$313
July
$294
August
$255
September
$288
October
$299
November
$291
December
$314
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Siesta Key. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Siesta Key

Find out more about Siesta Key

Everything you need to know about Siesta Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Siesta Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Siesta Key vacation 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 low season months. For more hustle and bustle, you may prefer to visit Siesta Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $171 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Siesta Key rentals

At Expedia, we put the best Siesta Key vacation 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 vacation.

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 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 like this Siesta Key vacation home rental. It comes with 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. Some other top choices in Siesta Key are Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times and Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND.

How many vacation rentals are there in Siesta Key?

With 808 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.