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, (69 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
$313 nightly
The price is $353
Jun 24 - Jun 25
Total with taxes and fees
Siesta Key Island Rentals

SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!

SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!
Siesta Key
9.4 out of 10, Exceptional, (31 reviews)
"Great place close to everything"
United States
Tracey M.
$428 nightly
The price is $477
Jul 7 - Jul 8
Total with taxes and fees
SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,268 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
$182 nightly
The price is $203
Jul 6 - Jul 7
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, (31 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
$305 nightly
The price is $311
Jun 28 - Jun 29
Total with taxes and fees
[escape to paradise] siesta key beach getaway

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (34 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.
$251 nightly
The price is $255
Jun 24 - Jun 25
Total with taxes and fees
[Beach Elements] pool view withprivate beach access

Walk to the Beach | Osprey Villa | Siesta Key

Walk to the Beach | Osprey Villa | Siesta Key
Siesta Key Village
9.8 out of 10, Exceptional, (19 reviews)
"Host was very helpful. The apt was very comfy"
United States
Barbara B.
$372 nightly
The price is $393
Jul 12 - Jul 13
Total with taxes and fees
Walk to the Beach | Osprey Villa | Siesta Key

Island Villa - Cozy Beach Retreat with Private dock

Island Villa - Cozy Beach Retreat with 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.
$388 nightly
The price is $404
Jun 26 - Jun 27
Total with taxes and fees
Island Villa - Cozy Beach Retreat with Private dock

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, (87 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
$324 nightly
The price is $361
Jun 28 - Jun 29
Total with taxes and fees
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

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, (76 reviews)
"Perfect location, super clean.comfortable"
United States
matthew w.
$376 nightly
The price is $407
Jun 25 - Jun 26
Total with taxes and fees
Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
$304 nightly
The price is $344
Jun 24 - Jun 25
Total with taxes and fees
Siesta Heron Suites & Villas

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, (33 reviews)
"Great stay with everything even better than expected. Very easy walk to the beach and a beach wagon made it even better. Would 100pct stay here again."
United States
ashlea p.
$530 nightly
The price is $591
Jun 28 - Jun 29
Total with taxes and fees
Lulu's Cozy Beach Cottage #2 | 5 Min. Walk to Beach | Dog OK | Pool | $185 Free Activities Daily!

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio
Siesta Key Village
9.8 out of 10, Exceptional, (11 reviews)
"Repeat guests! Great location and exactly what we needed for amenities! Property was clean and host made everything from check in to check out very easy! "
United States
Christine H.
$640 nightly
The price is $713
Jul 7 - Jul 8
Total with taxes and fees
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

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, (40 reviews)
"Great little place -perfect for a few days in siesta "
United States
Linda K.
$274 nightly
The price is $306
Jun 30 - Jul 1
Total with taxes and fees
2 Bedroom 2 Bath home near Siesta Key Beach

Everglades Villa • Sleeps 8 • Walk to Siesta Beach

Everglades Villa • Sleeps 8 • Walk to Siesta Beach
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.
$472 nightly
The price is $498
Jun 24 - Jun 25
Total with taxes and fees
Everglades Villa • Sleeps 8 • Walk to Siesta Beach

House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!
South Village
9.2 out of 10, Wonderful, (139 reviews)
"The condo was clean, modern and comfortable for our stay in Siesta. The beach was beautiful and the location was super convenient with restaurants and bars within walking distance. We would highly recommend!"
United States
Sandy M.
House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

Tiny House Green Lifeguard Stand - sleeps 5

Tiny House Green Lifeguard Stand - sleeps 5
Sarasota
9.4 out of 10, Exceptional, (32 reviews)
"The area is quiet. The house is in a side road near a strip plaza. It’s cute and good for the tiny home experience. The microwave in our home looked pretty damaged on the inside. We did not use it but the stove top worked great!"
United States
JONELL
$176 nightly
The price is $196
Jun 24 - Jun 25
Total with taxes and fees
Tiny House Green Lifeguard Stand - sleeps 5

Siesta Key Studio close to beaches, city, and airport.

Siesta Key Studio close to beaches, city, and airport.
Siesta Key
8.4 out of 10, Very Good, (12 reviews)
"Fantastic experience, great host, and close to everything!"
United States
Shannon
$177 nightly
The price is $198
Jun 30 - Jul 1
Total with taxes and fees
Siesta Key Studio close to beaches, city, and airport.

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
$431 nightly
The price is $487
Jul 6 - Jul 7
Total with taxes and fees
The Inn On Siesta Key

Gulf Villa - 3 min to #1 Beach - Pool

Gulf Villa - 3 min to #1 Beach - Pool
Siesta Key Village
9.0 out of 10, Wonderful, (15 reviews)
"Very cute & clean. Great location!"
United States
Nannette
$518 nightly
The price is $550
Jun 30 - Jul 1
Total with taxes and fees
Gulf Villa - 3 min to #1 Beach - Pool

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (370 reviews)
"Loved the tiny house will stay there again!"
United States
Nydia
$184 nightly
The price is $208
Jun 30 - Jul 1
Total with taxes and fees
Tiny House Siesta
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
Next month
May
March
$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 $203 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.

Explore a world of travel with Expedia

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 give good reviews to this Siesta Key vacation home rental, which 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. Another good choice for your trip to Siesta Key is 3-bed 2-bathroom Siesta Key townhome close to village,beaches, city and airport.

How many vacation rentals are there in Siesta Key?

With 417 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 Turtle 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 St. Armands Circle 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.