A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

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 homes

1. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.4 out of 10, Exceptional, (81 reviews)
"The property was clean and had great decor! They provide everything you need for the beach and the pool is a great added bonus. Perfect location with being so close the restaurants and the beach. We are already planning our next stay!"
United States
Meghan
The price is CA $140
CA $452 total
includes taxes & fees
Sep 30 - Oct 1
Siesta Key Island Rentals

2. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (45 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is CA $129
CA $429 total
includes taxes & fees
Sep 28 - Sep 29
Siesta Heron Suites & Villas

3. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Beautiful stay , I walked each day to the beach and really is 13 min walk to get to the beach - pickle ball courts available to play in the morning -the beach is excellent - the place have everything we need beds and shower was really nice -Really excellent we will come back."
United States
Moreixa C.
The price is CA $127
CA $410 total
includes taxes & fees
Sep 27 - Sep 28
[lounge like locals] walk to siesta beach +bikes

4. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (219 reviews)
"The host was very communicative and responsive. The pool was a big hit for our family. Comfy beds and a convenient drive to the beach and other venues. Would definitely stay here again. "
United States
Jennifer M.
The price is CA $171
CA $654 total
includes taxes & fees
Sep 24 - Sep 25
Siesta beach....one and only

5. The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
Sarasota
10.0 out of 10, Exceptional, (4 reviews)
"Traveled with my kids and this place was so great! Super cute and comfortable. We loved the Mermaid Tiny House."
United States
Kadina A.
The price is CA $122
CA $232 total
includes taxes & fees
Sep 30 - Oct 1
The Mermaid at Tiny House Siesta

6. Dolphin Villa - Pool - Steps to Siesta Key Village

Dolphin Villa - Pool - Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"Great location to downtown, beach. Kitchen and furnishing updated and in great condition. Negatives would be the lock on the backdoor, air conditioning from the ceiling that could not be controlled from our apartment. The pool was great and had plenty of seating. Only issue with the Dolphin apartment is the many windows, which kind of made it feel like living in a fish bowl. That might not be an issues for others. "
United States
Sandra C.
The price is CA $138
CA $496 total
includes taxes & fees
Sep 24 - Sep 25
Dolphin Villa - Pool - Steps to Siesta Key Village

7. Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
South Village
9.6 out of 10, Exceptional, (72 reviews)
"It was very clean and close to the beach. Perfect location."
United States
Cortney
The price is CA $226
CA $741 total
includes taxes & fees
Sep 24 - Sep 25
Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

8. Island Villa | Cozy Beach Retreat | Walk to Village

Island Villa | Cozy Beach Retreat | Walk to Village
Siesta Key Village
8.4 out of 10, Very good, (14 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
The price is CA $138
CA $546 total
includes taxes & fees
Sep 28 - Sep 29
Island Villa | Cozy Beach Retreat | Walk to Village

9. Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly

Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly
Siesta Key Village
9.6 out of 10, Exceptional, (22 reviews)
"Great location to walk to siesta key village. "
United States
N A.
The price is CA $199
CA $856 total
includes taxes & fees
Sep 24 - Sep 25
Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly

10. Sea Turtle- Full Sized living at Tiny House Siesta

Sea Turtle- Full Sized living at Tiny House Siesta
Sarasota
9.4 out of 10, Exceptional, (18 reviews)
"The Tiny House is a perfect location to explore Siesta Key and the surrounding areas. It had just what we needed but was in close proximity (walking distance) to many bars and restaurants but was still exceptionally quiet."
United States
Wayne
The price is CA $143
CA $257 total
includes taxes & fees
Sep 30 - Oct 1
Sea Turtle- Full Sized living at Tiny House Siesta

11. FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West
South Village
9.2 out of 10, Wonderful, (7 reviews)
"We had an incredible stay and this is such a great option IN siesta Key that is close to the beaches, has private beach access and is a stand alone building. The unit also has an outdoor shower which was such a great surprise. We will be back!"
United States
Amber M.
The price is CA $203
CA $931 total
includes taxes & fees
Sep 24 - Sep 25
FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

12. 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, (15 reviews)
"We loved staying here for my bachelorette!"
United States
Kelsey E.
The price is CA $204
CA $632 total
includes taxes & fees
Oct 6 - Oct 7
Everglades Villa • Sleeps 8 • Walk to Siesta Beach

13. Modern 2BR Retreat · Heated Pool · Near Siesta

Modern 2BR Retreat · Heated Pool · Near Siesta
Sarasota
10.0 out of 10, Exceptional, (3 reviews)
"Property was clean, the host was friendly, and the house in general was beautiful and a great place to stay!"
United States
Maria V.
The price is CA $141
CA $511 total
includes taxes & fees
Sep 28 - Sep 29
Modern 2BR Retreat · Heated Pool · Near Siesta

14. Private Beach Access w/shared Pool -Casita East

Private Beach Access w/shared Pool -Casita East
South Village
9.4 out of 10, Exceptional, (6 reviews)
"Great stay overall! Check-in was smooth and hassle-free, and the unit was very clean upon arrival. It had everything we needed for a comfortable visit, though a few additional amenities would have made it even better. That said, we really enjoyed our stay and would definitely consider coming back."
United States
John H.
The price is CA $203
CA $931 total
includes taxes & fees
Sep 24 - Sep 25
Private Beach Access w/shared Pool -Casita East

15. Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach

Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach
Sarasota
The price is CA $110
CA $218 total
includes taxes & fees
Sep 30 - Oct 1
Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach

16. Salty Summer – Steps to Siesta Key Village & Beach

Salty Summer – Steps to Siesta Key Village & Beach
Siesta Key Village
10.0 out of 10, Exceptional, (6 reviews)
"Check in was easy! Communication was awesome! And would definitely recommend to anyone going to Siesta Key! We loved it! "
United States
Stephanie S.
The price is CA $277
CA $907 total
includes taxes & fees
Sep 24 - Sep 25
Salty Summer – Steps to Siesta Key Village & Beach

17. Beautiful 2 Bedroom Duplex Steps Away from the Beach

Beautiful 2 Bedroom Duplex Steps Away from the Beach
South Village
9.4 out of 10, Exceptional, (3 reviews)
"The property is beautiful! It was everything we wanted and needed. Very clean with all the amenities. The hostess responded promptly when ever we contacted them and the check-in and out was so simple! Loved that we could walk to grab a bite to eat or just check out some shopping. The best part was the 3 min walk to the private beach which was very clean and the perfect beach for shelling! We loved this place so much we are concerning rented both 1 and 2 units next season so we can bring our...
United States
Tajsha G.
The price is CA $192
CA $834 total
includes taxes & fees
Sep 28 - Sep 29
Beautiful 2 Bedroom Duplex Steps Away from the Beach

18. Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
Siesta Key
9.4 out of 10, Exceptional, (70 reviews)
"We enjoyed the space this property offered our party of 6. We also appreciated the beach side location and proximity to restaurants and shops. We would stay here again."
United States
Meredith S.
The price is CA $349
CA $927 total
includes taxes & fees
Sep 24 - Sep 25
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

19. Condo with Private Beach Access, Great Shared Amenities - Private Beach House

Condo with Private Beach Access, Great Shared Amenities - Private Beach House
Siesta Key
9.2 out of 10, Wonderful, (50 reviews)
"Our stay at Private Beach House was excellent! The location was perfect, the beach was beautiful, and the house was very comfortable and convenient. We absolutely enjoyed our time there and would definitely stay again. We did have an issue with the water for one night, but we called and they were very responsive and had it resolved in less than an hour. We really appreciated how quickly they took care of it. Overall, we had a wonderful stay and would definitely recommend Private Beach House!"
United States
Kelmarie
The price is CA $280
CA $1,205 total
includes taxes & fees
Sep 25 - Sep 26
Condo with Private Beach Access, Great Shared Amenities - Private Beach House

20. Sea Escape - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Escape - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Siesta Key Village
10.0 out of 10, Exceptional, (25 reviews)
"Nice little spot that very close to the beach and everything else in the village. You can just park and not have to get in your vehicle the entire stay."
United States
Michael J.
The price is CA $469
CA $855 total
includes taxes & fees
Sep 26 - Sep 27
Sea Escape - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
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

Siesta Key Vacation Homes information

Number of reviews
486
Accommodation
900 Vacation Homes
Lowest Price
CA $218
Highest Price
CA $1,205

Explore a world of travel with Expedia