Siesta Key Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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.
The price is CA $226
CA $512 total
includes taxes & fees
Jun 9 - Jun 10
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
The price is CA $175
CA $475 total
includes taxes & fees
Jun 2 - Jun 3
Siesta Heron Suites & Villas

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,261 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
The price is CA $260
CA $317 total
includes taxes & fees
Jun 2 - Jun 3
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.
The price is CA $139
CA $447 total
includes taxes & fees
Jun 3 - Jun 4
[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
The price is CA $213
CA $589 total
includes taxes & fees
Jun 3 - Jun 4
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.
The price is CA $226
CA $563 total
includes taxes & fees
Jun 2 - Jun 3
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.
The price is CA $274
CA $639 total
includes taxes & fees
Jun 5 - Jun 6
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.
The price is CA $213
CA $510 total
includes taxes & fees
Jun 10 - Jun 11
[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
The price is CA $226
CA $472 total
includes taxes & fees
Jun 8 - Jun 9
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.
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.
The price is CA $382
CA $715 total
includes taxes & fees
Jun 2 - Jun 3
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
The price is CA $265
CA $534 total
includes taxes & fees
Jun 9 - Jun 10
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, (5,533 reviews)
"Clean room and convenient to the beach."
United States
Jacqueline
The price is CA $257
CA $326 total
includes taxes & fees
Jun 8 - Jun 9
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
The price is CA $262
CA $448 total
includes taxes & fees
Jun 8 - Jun 9
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.
The price is CA $346
CA $801 total
includes taxes & fees
Jul 1 - Jul 2
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
The price is CA $360
CA $788 total
includes taxes & fees
Jun 17 - Jun 18
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.
The price is CA $246
CA $507 total
includes taxes & fees
Jun 2 - Jun 3
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
The price is CA $263
CA $450 total
includes taxes & fees
Jun 4 - Jun 5
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
The price is CA $248
CA $511 total
includes taxes & fees
Jun 3 - Jun 4
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.
Save an average of 15% on thousands of hotels when you're signed in

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 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.