Siesta Key Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Siesta Key vacation rentals

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 ￥24,525
￥61,438 total
includes taxes & fees
May 25 - May 26
[escape to paradise] siesta key beach getaway
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 ￥26,033
￥56,987 total
includes taxes & fees
Jun 9 - Jun 10
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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)
"Very nice, clean and quiet place."
United States
Monika Z.
The price is ￥40,077
￥76,225 total
includes taxes & fees
May 21 - May 22
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Beach

[Sunny in Siesta] king bed + walk to beach

[Sunny in Siesta] king bed + walk to beach
South Village
9.8 out of 10, Exceptional, (13 reviews)
"Great location and accommodation. "
United States
ESTELEN
The price is ￥14,715
￥43,974 total
includes taxes & fees
May 20 - May 21
[Sunny in Siesta] king bed + walk to beach
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 ￥24,644
￥67,145 total
includes taxes & fees
May 29 - May 30
Newly Renovated Beach-Side villa | Pool | Dock
House (3 Bedrooms) | Interior

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very Good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
The price is ￥29,049
￥85,470 total
includes taxes & fees
Jun 11 - Jun 12
Unwind Poolside + Walk to Beach! Sarasota Retreat
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, (127 reviews)
"Enjoyed our stay great location easy walk to village and the beach"
United States
Gregory
The price is ￥45,564
￥51,487 total
includes taxes & fees
May 27 - May 28
SeaSpray Resort
2 bedrooms, iron/ironing board, WiFi, bed sheets

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 ￥23,732
￥71,821 total
includes taxes & fees
May 20 - May 21
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ
Terrace/patio

2 Bedroom 2 Bath home near Siesta Key Beach

2 Bedroom 2 Bath home near Siesta Key Beach
Sarasota
8.6 out of 10, Excellent, (39 reviews)
"House was conveniently located. "
United States
CHRISTINE V.
The price is ￥22,859
￥41,562 total
includes taxes & fees
Jun 16 - Jun 17
2 Bedroom 2 Bath home near Siesta Key Beach
Beach nearby, sun loungers, beach towels

Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (47 reviews)
"The apartment is clean and comfortable! Location is amazing! The beach, restaurants, and bars are all very close. The beach is great and easily accessible. 100% would stay here again! "
United States
Alex
The price is ￥26,017
￥64,454 total
includes taxes & fees
May 20 - May 21
Siesta Key Village-Suite #1: A block to the Beach!
Condo (LuLu's Key House Leatherback 2/2 Down) | Exterior

Lulu's Key House Leatherback 2/2 Downstairs

Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
Siesta Key Village
The price is ￥51,281
￥107,099 total
includes taxes & fees
Jun 3 - Jun 4
Lulu's Key House Leatherback 2/2 Downstairs
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 ￥16,841
￥50,959 total
includes taxes & fees
May 20 - May 21
Siesta Heron Suites & Villas
Beach nearby

Beachside Studio Located Across from Main Beach and Half Mile to Village

Beachside Studio Located Across from Main Beach and Half Mile to Village
Sarasota
8.8 out of 10, Excellent, (164 reviews)
"Useful place, everything was clean and it has a good location."
United States
Felipe
Beachside Studio Located Across from Main Beach and Half Mile to Village
Beach nearby, beach umbrellas

Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
South Village
9.0 out of 10, Wonderful, (84 reviews)
"Nice clean room, great location. Close to the beach. No hassle when we arrived at 1:30p, let us in the room. Overall, a great experience. "
United States
David A.
The price is ￥31,431
￥61,776 total
includes taxes & fees
Jun 1 - Jun 2
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
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 ￥26,470
￥75,259 total
includes taxes & fees
May 20 - May 21
Modern beach Retreat | Canal view | Private dock
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 ￥14,388
￥44,366 total
includes taxes & fees
May 20 - May 21
[Beach Elements] pool view withprivate beach access
Beach nearby, sun loungers, beach towels, snorkeling

Fully renovated Siesta Key Condo | Walk to Beach | Pool | Dog OK | Perfect Location in SK Village

Fully renovated Siesta Key Condo | Walk to Beach | Pool | Dog OK | Perfect Location in SK Village
Siesta Key Village
9.4 out of 10, Exceptional, (82 reviews)
"This condo has been nicely appointed and has everything you need for a beach vacation. It's also in the village near all shops and eateries. "
United States
Abi-Gayil G.
The price is ￥23,890
￥91,159 total
includes taxes & fees
May 20 - May 21
Fully renovated Siesta Key Condo | Walk to Beach | Pool | Dog OK | Perfect Location in SK Village
Sun loungers, beach towels

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is ￥15,715
￥47,792 total
includes taxes & fees
May 30 - May 31
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Beach nearby, sun loungers, beach towels, snorkeling

Lulu's Cozy Beach Cottage #2 | 5 Min. Walk to Beach | Dog OK | Pool | $185 Free Activities Daily!

Lulu's Cozy Beach Cottage #2 | 5 Min. Walk to Beach | Dog OK | Pool | $185 Free Activities Daily!
Sarasota
10.0 out of 10, Exceptional, (31 reviews)
Lulu's Cozy Beach Cottage #2 | 5 Min. Walk to Beach | Dog OK | Pool | $185 Free Activities Daily!
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 Island Rentals

Siesta Key Island Rentals

10/10 Excellent
"I would highly recommend 447 Canal Street. It was beautiful, clean, updated and comfortable. There were a lot of stairs so consider that when planning your trip. Love that it has its own pool. All the dishes and pots/pans/utensils were new and desirable for use. We will be returning!"
Melissa 4-night trip
Posted 5 hours ago
Siesta Key Island Rentals

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 Steps to Siesta Key Beach & Village - 2BR w Balcony, 1945 Triplex 2nd Floor.

How many vacation rentals are there in Siesta Key?

With 410 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.