Siesta Key Vacation Rentals

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Our top choices for Siesta Key vacation rentals

Beachside villa in Siesta Key | Canal Front | pool

Beachside villa in Siesta Key | Canal Front | pool
Siesta Key Village
9.8 out of 10, Exceptional, (19 reviews)
"Nice clean and a short walk to everything!"
United States
Ralph S.
The price is CA $329
CA $708 total
includes taxes & fees
May 3 - May 4
Beachside villa in Siesta Key | Canal Front | pool

Beachy Sarasota Duplex

Beachy Sarasota Duplex
Sarasota
10.0 out of 10, Exceptional, (4 reviews)
"Great experience. House was in a great location and having a Dunkin walking distance was a plus. Definitely would recommend. Thank you A"
United States
pete t.
The price is CA $189
CA $633 total
includes taxes & fees
May 10 - May 11
Beachy Sarasota Duplex

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 CA $206
CA $489 total
includes taxes & fees
Apr 14 - Apr 15
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

[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 CA $184
CA $500 total
includes taxes & fees
Apr 14 - Apr 15
[escape to paradise] siesta key beach getaway

Sarasota Duplex near Siesta Key

Sarasota Duplex near Siesta Key
Sarasota
9.4 out of 10, Exceptional, (6 reviews)
"We enjoyed our stay! Location was great!!"
United States
Jacy N.
The price is CA $156
CA $592 total
includes taxes & fees
May 6 - May 7
Sarasota Duplex near Siesta Key

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 CA $137
CA $421 total
includes taxes & fees
Apr 13 - Apr 14
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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 CA $231
CA $660 total
includes taxes & fees
Apr 14 - Apr 15
Modern beach Retreat | Canal view | Private dock

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 CA $227
CA $565 total
includes taxes & fees
Apr 13 - Apr 14
Siesta Key Village-Suite #1: A block to the Beach!

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, (13 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 CA $323
CA $778 total
includes taxes & fees
Apr 15 - Apr 16
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (41 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is CA $176
CA $477 total
includes taxes & fees
Apr 15 - Apr 16
Siesta Heron Suites & Villas

Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (47 reviews)
"Beautiful place close to the beach’s and love it would stay here again "
United States
Steve D.
The price is CA $179
CA $411 total
includes taxes & fees
Apr 15 - Apr 16
Siesta Key, Sea Horse Villa, Pool. Daily rentals

Tiny Coral Oasis- beachy tiny house for your getaway

Tiny Coral Oasis- beachy tiny house for your getaway
Sarasota
9.0 out of 10, Wonderful, (20 reviews)
"Cute tiny house Clean and comfortable Had a great time"
United States
DeAnna T.
The price is CA $149
CA $279 total
includes taxes & fees
Apr 15 - Apr 16
Tiny Coral Oasis- beachy tiny house for your getaway

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, (115 reviews)
"Convenient location - close to beach. Umbrella & beach chairs in closet came in handy. "
United States
Mary
The price is CA $224
CA $479 total
includes taxes & fees
Apr 13 - Apr 14
Bright & Beachy–Beach Club Siesta Key 100A by RVA

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, (163 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

VILLA 3 · Siesta Key, Pool View. Walk to Beach. Daily Rentals

VILLA 3 · Siesta Key, Pool View. Walk to Beach. Daily Rentals
Sarasota
9.6 out of 10, Exceptional, (44 reviews)
"The location of the property could not have been better. A very short walk to the quietest beach on Siesta Key. The manager was very attentive when we called with a minor issue and had it resolved quickly. The property could use a pretty thorough cleaning of the baseboards and other nooks and crannies but overall it was pretty clean. We would stay again."
United States
Mel S.
The price is CA $218
CA $462 total
includes taxes & fees
Apr 14 - Apr 15
VILLA 3 · Siesta Key, Pool View. Walk to Beach. Daily Rentals

Tiny House Green Lifeguard Stand - sleeps 5

Tiny House Green Lifeguard Stand - sleeps 5
Sarasota
9.4 out of 10, Exceptional, (29 reviews)
"It was a great fit for our family and we enjoyed the experience. "
United States
Stephanie H.
The price is CA $156
CA $287 total
includes taxes & fees
Apr 13 - Apr 14
Tiny House Green Lifeguard Stand - sleeps 5

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, (159 reviews)
"Pristinely clean comfortable and very close to beach with free parking it was a great place to stay! Would recommend!"
United States
Stina
The price is CA $317
CA $518 total
includes taxes & fees
Apr 15 - Apr 16
Studio Retreat Across the Street from Beautiful Siesta Key Beach

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (196 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
The Inn On Siesta Key

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, (36 reviews)
"Very nice, clean and quiet place."
United States
Monika Z.
The price is CA $388
CA $723 total
includes taxes & fees
Apr 29 - Apr 30
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (46 reviews)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
The price is CA $193
CA $429 total
includes taxes & fees
Apr 13 - Apr 14
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
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

Find out more about Siesta Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Siesta Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool and Gull Villa – Spacious 2BR, Walk to Siesta Key & Village, 1945 Triplex .

How many vacation rentals are there in Siesta Key?

With 395 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. While here, Crescent Beach and Siesta Key Marina 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.