Siesta Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 24 - Oct 26
In one month
Nov 7 - Nov 9
In two months
Dec 5 - Dec 7
In three months
Jan 2 - Jan 4

Vacation 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, (5027)
"Great place and loved the closeness to the beach!"
The price is ￥19,148
￥25,055 total
includes taxes & fees
Oct 13 - Oct 14
Tropical Beach Resorts
Captiva Beach Resort
Front of property - evening/night

Captiva Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (1142)
"2nd time and excellent as always..close to the beach and great surroundings "
Captiva Beach Resort
SeaSpray Resort
Deluxe Suite, 2 Bedrooms | Living area

SeaSpray Resort

4.0 star property
9.6 out of 10, Exceptional, (47)
"I love everything about this place so beautiful with walking distance to the beach "
The price is ￥34,623
￥39,124 total
includes taxes & fees
Oct 20 - Oct 21
SeaSpray Resort
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (330)
"We liked the stay very much "
The Ringling Beach House
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, (292)
"Loved our stay! "
The price is ￥66,402
￥82,722 total
includes taxes & fees
Nov 10 - Nov 11
The Residences at Siesta Key Beach by Hyatt Vacation Club
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
Siesta Palms By the Beach
Garden

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (132)
"We loved the condo. The distance to the beach was amazing. The wagon and beach chairs that were provided were so nice! The condo was clean and in great shape. The pool/ outdoor area was beautiful! We couldn’t have asked for a better place! "
Siesta Palms By the 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, (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. "
The price is ￥23,134
￥53,076 total
includes taxes & fees
Oct 13 - Oct 14
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, (184)
"clean and close proximity to beach and restaurants"
The Inn On Siesta Key
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
Private Home Directly on Siesta Key Beach!
On the beach

Private Home Directly on Siesta Key Beach!

9.8 out of 10, Exceptional, (6)
"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!! "
Private Home Directly on Siesta Key Beach!
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!
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, (66)
"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
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!

9.8 out of 10, Exceptional, (6)
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!
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, (37)
"It was perfect for my family of 4 for our beach vacation!!"
Siesta Heron Suites & Villas
Coastal Cottage - Direct Beach Access
Fridge, microwave, stovetop, dishwasher

Coastal Cottage - Direct Beach Access

Coastal Cottage - Direct Beach Access
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, (25)
"Location was great! Alex was very helpful and quick to respond. Definitely recommend this place to stay in the beautiful Siesta Key!"
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
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, (63)
"Great location!"
The price is ￥48,670
￥104,290 total
includes taxes & fees
Oct 14 - Oct 15
Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West
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
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, (53)
"House was very nice. Was clean when we arrived. Plenty of space and beautiful view "
The price is ￥60,174
￥137,431 total
includes taxes & fees
Oct 19 - Oct 20
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

The Ringling Beach House

The Ringling Beach House

10/10 Excellent
"Apartment was big,very clean. The carts, chairs and coolers to take to the beach were a great perk! Close to the beach and within walking distance to Siesta Key Village."
Susan 2-night trip
Posted 2 days ago
The Ringling Beach House

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:

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

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 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. Some other top choices in Siesta Key are Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times and Coastal Cottage - Direct Beach Access.

How many vacation rentals are there in Siesta Key?

With 817 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.