Siesta Key Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Siesta Key vacation rentals

5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (68 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
The price is ￥18,928
￥54,850 total
includes taxes & fees
May 31 - Jun 1
Siesta Key Island Rentals
Outdoor dining

Newly Renovated Beach-Side villa | Pool | Dock

Newly Renovated Beach-Side villa | Pool | Dock
Siesta Key Village
9.4 out of 10, Exceptional, (16 reviews)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is ￥25,456
￥68,036 total
includes taxes & fees
Jun 3 - Jun 4
Newly Renovated Beach-Side villa | Pool | Dock
2 bedrooms, iron/ironing board, WiFi, bed sheets

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is ￥21,160
￥58,036 total
includes taxes & fees
May 31 - Jun 1
[escape to paradise] siesta key beach getaway
Beach nearby, white sand, beach umbrellas, beach towels

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The Inn On Siesta Key
Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (131 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
The price is ￥39,521
￥44,657 total
includes taxes & fees
Jun 2 - Jun 3
SeaSpray Resort
Beach

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is ￥26,117
￥58,126 total
includes taxes & fees
Jun 9 - Jun 10
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,260 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
The price is ￥32,771
￥39,730 total
includes taxes & fees
Jun 1 - Jun 2
Captiva Beach Resort
Beach nearby

Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Siesta Key Village
10.0 out of 10, Exceptional, (31 reviews)
"Great location well kept and host was very responsive "
United States
Eric M.
The price is ￥51,544
￥104,931 total
includes taxes & fees
Jun 2 - Jun 3
Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Beach nearby, sun loungers, beach towels

Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (75 reviews)
"Perfect location, super clean.comfortable"
United States
matthew w.
The price is ￥26,101
￥64,184 total
includes taxes & fees
Jun 9 - Jun 10
Siesta Key Village-Suite #3: A Block to the Beach!
Beach

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (30 reviews)
"The space was clean and well-equipped, and the host was easily reachable and responded quickly when I asked a question. The private beach access was nice. I would stay here again. "
United States
Natalie M.
The price is ￥25,588
￥59,182 total
includes taxes & fees
Jun 9 - Jun 10
[Beach Elements] pool view withprivate beach access
TV, music library

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Siesta Key
9.4 out of 10, Exceptional, (98 reviews)
"Great location"
United States
Daphane
The price is ￥35,685
￥60,772 total
includes taxes & fees
Jun 3 - Jun 4
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very Good, (43 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is ￥23,134
￥58,179 total
includes taxes & fees
Jun 2 - Jun 3
Siesta Heron Suites & Villas
Beach nearby

Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
South Village
9.8 out of 10, Exceptional, (33 reviews)
"Private, nice, and new Easy access Would stay again "
United States
Frederick
The price is ￥22,187
￥42,687 total
includes taxes & fees
Jun 2 - Jun 3
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
A heated pool

JUST One Block From Beach and One Block From Village – Island Time East

JUST One Block From Beach and One Block From Village – Island Time East
Siesta Key Village
9.6 out of 10, Exceptional, (50 reviews)
"Customer service was great, they were very welcoming and had a quick response time to any issues or concerns we had.Although our last night was very unpleasant due to pool equipment issues (which was unfortunate; however, out of their control) our over all stay was awesome."
United States
Karen K.
The price is ￥40,131
￥168,052 total
includes taxes & fees
Jun 1 - Jun 2
JUST One Block From Beach and One Block From Village – Island Time East
Fridge, microwave, oven, stovetop

Condo with Private Beach Access, Great Shared Amenities - Private Beach House

Condo with Private Beach Access, Great Shared Amenities - Private Beach House
Siesta Key
9.2 out of 10, Wonderful, (46 reviews)
"Very nice property! Beautiful beach! We had a problem with one of the showers and it was solved right away.The communication with the management was excellent , they reached to us several times though texts to make sure everything was ok.We highly recommend this property!"
United States
Fernanda L.
The price is ￥34,221
￥138,722 total
includes taxes & fees
Jun 7 - Jun 8
Condo with Private Beach Access, Great Shared Amenities - Private Beach House
Outdoor dining

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ
Siesta Key Village
9.0 out of 10, Wonderful, (14 reviews)
"We enjoyed our stay at Everglades Villa. The location was the best feature as we were able to walk to Siesta Key Village and the beach. "
United States
Lisa S.
The price is ￥32,598
￥82,389 total
includes taxes & fees
May 31 - Jun 1
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ
Beach nearby

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Siesta Key
9.2 out of 10, Wonderful, (37 reviews)
"Everything was perfect. Location great, condition of property excellent, ease of access perfect. Just wish I could stay longer!"
United States
Michael V.
The price is ￥46,603
￥84,495 total
includes taxes & fees
Jun 2 - Jun 3
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Property grounds

Modern beach Retreat | Canal view | Private dock

Modern beach Retreat | Canal view | Private dock
Siesta Key Village
8.4 out of 10, Very Good, (13 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
The price is ￥26,555
￥75,023 total
includes taxes & fees
Jun 1 - Jun 2
Modern beach Retreat | Canal view | Private dock
Property grounds

Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool

Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool
Siesta Key
8.6 out of 10, Excellent, (22 reviews)
"Loved the water view"
United States
Gina
The price is ￥26,117
￥53,349 total
includes taxes & fees
Jun 9 - Jun 10
Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool
Outdoor dining

Perfect Location minutes to beach and downtown with heated pool and hot tub

Perfect Location minutes to beach and downtown with heated pool and hot tub
Sarasota
9.8 out of 10, Exceptional, (8 reviews)
"Host was great! Location excellent! I would definitely stay again! "
United States
Laurie G.
The price is ￥25,627
￥55,969 total
includes taxes & fees
Jun 8 - Jun 9
Perfect Location minutes to beach and downtown with heated pool and hot tub
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 Beachside Villas

Siesta Key Beachside Villas

10/10 Excellent
"Office staff was friendly and very helpful. Villa was clean and a great location. Would highly recommend to family and friends."
Robert 3-night trip
Posted 2 hours ago
Siesta Key Beachside Villas

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 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 3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport and Last Minute Luxury Beachside Home 100 ft Walk to Siesta Key Beach Pool.

How many vacation rentals are there in Siesta Key?

With 408 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 Shell Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jim Neville Marine Preserve. You’ll find favorite places to visit like Lido Beach and Venice Beach in the larger area.

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.