Siesta Key Vacation Rentals

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Our top choices for Siesta Key vacation rentals

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
Siesta Key Island Rentals

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.
$369 nightly
The price is $369
Jun 9 - Jun 10
Total with taxes and fees
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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
$291 nightly
The price is $329
Jun 4 - Jun 5
Total with taxes and fees
Siesta Heron Suites & Villas

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,262 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
$216 nightly
The price is $242
Jun 4 - Jun 5
Total with taxes and fees
Captiva Beach Resort

[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.
$359 nightly
The price is $367
Jun 11 - Jun 12
Total with taxes and fees
[escape to paradise] siesta key beach getaway

Newly Renovated Beach-Side villa | Pool | Dock

Newly Renovated Beach-Side villa | Pool | Dock
Siesta Key Village
9.4 out of 10, Exceptional, (17 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
$399 nightly
The price is $419
Jun 9 - Jun 10
Total with taxes and fees
Newly Renovated Beach-Side villa | Pool | Dock

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.
$358 nightly
The price is $389
Jun 7 - Jun 8
Total with taxes and fees
Siesta Key Village-Suite #3: A Block to the Beach!

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Siesta Key
9.8 out of 10, Exceptional, (118 reviews)
"Stay was great. "
United States
Carol B.
$411 nightly
The price is $458
Jun 5 - Jun 6
Total with taxes and fees
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key 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.
$330 nightly
The price is $338
Jun 9 - Jun 10
Total with taxes and fees
[Beach Elements] pool view withprivate beach access

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
$334 nightly
The price is $334
Jun 11 - Jun 12
Total with taxes and fees
Siesta Key ~New Waterview studio ~ sleeps 4 ~ pool

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.
$272 nightly
The price is $303
Jun 10 - Jun 11
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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.
$437 nightly
The price is $487
Jun 4 - Jun 5
Total with taxes and fees
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
South Village
8.8 out of 10, Excellent, (86 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
$342 nightly
The price is $381
Jun 4 - Jun 5
Total with taxes and fees
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,534 reviews)
"Clean room and convenient to the beach."
United States
Jacqueline
$209 nightly
The price is $236
Jun 8 - Jun 9
Total with taxes and fees
Tropical Beach Resorts

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, (165 reviews)
"Useful place, everything was clean and it has a good location."
United States
Felipe
$267 nightly
The price is $298
Jun 8 - Jun 9
Total with taxes and fees
Beachside Studio Located Across from Main Beach and Half Mile to Village

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.
$503 nightly
The price is $533
Jun 16 - Jun 17
Total with taxes and fees
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Lulu's Key House Kemp Ridley 1/1 Downstairs

Lulu's Key House Kemp Ridley 1/1 Downstairs
3.5 star property
Siesta Key Village
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely beautiful place. Very clean, easy check-in, wonderful location"
United States
Christine
$502 nightly
The price is $565
Jun 17 - Jun 18
Total with taxes and fees
Lulu's Key House Kemp Ridley 1/1 Downstairs

Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (104 reviews)
"Awesome location and the staff was great!"
United States
John F.
$325 nightly
The price is $362
Jun 4 - Jun 5
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Studio Retreat Across the Street from Beautiful Siesta Key Beach

Studio Retreat Across the Street from Beautiful Siesta Key Beach
Siesta Key
8.8 out of 10, Excellent, (163 reviews)
"It was a great place. And just about a 5 min walk to the beach. "
United States
DESIREE
$262 nightly
The price is $292
Jun 4 - Jun 5
Total with taxes and fees
Studio Retreat Across the Street from Beautiful Siesta Key Beach

Bright & Beachy–Beach Club Siesta Key 100A by RVA

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (118 reviews)
"Convenient location - close to beach. Umbrella & beach chairs in closet came in handy. "
United States
Mary
$331 nightly
The price is $369
Jun 8 - Jun 9
Total with taxes and fees
Bright & Beachy–Beach Club Siesta Key 100A by RVA
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

Less expensive
More expensive
This month
Next month
May
March
$398
$403
Month
Price
January
$418
February
$509
March
$542
April
$406
May
$339
June
$398
July
$403
August
$348
September
$343
October
$339
November
$385
December
$428
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

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 $236 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 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 414 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.