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

Siesta Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Siesta Key vacation homes

A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

1. 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)
"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 $193
CA $574 total
includes taxes & fees
Oct 13 - Oct 14
Dolphin Villa - Pool - Steps to Siesta Key Village
A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

2. [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 $110
CA $416 total
includes taxes & fees
Oct 5 - Oct 6
[lounge like locals] walk to siesta beach +bikes
A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

3. 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 $148
CA $564 total
includes taxes & fees
Oct 5 - Oct 6
Island Villa | Cozy Beach Retreat | Walk to Village
An aerial view of a beach with clear skies, a sandy shore, and a mix of greenery and paths.

4. 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 $182
CA $842 total
includes taxes & fees
Oct 5 - Oct 6
Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly
A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

5. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (46 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is CA $135
CA $439 total
includes taxes & fees
Oct 8 - Oct 9
Siesta Heron Suites & Villas
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

6. 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 $180
CA $606 total
includes taxes & fees
Oct 5 - Oct 6
Everglades Villa • Sleeps 8 • Walk to Siesta Beach
A beach with waves and a bird flying near the shore.

7. 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 $124
CA $249 total
includes taxes & fees
Oct 13 - Oct 14
The Mermaid at Tiny House Siesta
A modern kitchen with a stainless steel refrigerator, granite countertop, white cabinetry, and a dining area with a table and chairs.

8. 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 $182
CA $828 total
includes taxes & fees
Oct 5 - Oct 6
Beautiful 2 Bedroom Duplex Steps Away from the Beach
An aerial view of a beach with clear skies, a sandy shore, and a mix of greenery and paths.

9. Pet Friendly home, Close to Sarasota Beach!

Pet Friendly home, Close to Sarasota Beach!
Siesta Key Village
9.0 out of 10, Wonderful, (8 reviews)
"Great house great location will definitely come back to this property "
United States
Matthew Y.
The price is CA $217
CA $888 total
includes taxes & fees
Oct 5 - Oct 6
Pet Friendly home, Close to Sarasota Beach!
An aerial view of a coastal resort area with beachfront hotels, a swimming pool, and a road.

10. Coastal 2 Bedroom Duplex Steps Away from the Beach

Coastal 2 Bedroom Duplex Steps Away from the Beach
South Village
9.6 out of 10, Exceptional, (5 reviews)
"Close to the beach, shops, food and trolley. The beach and pool were great! It was nice to have access to beach towels, wagon and cooler from the host since we flew down. Check in was super easy and host communication was excellent..even warning us about possible traffic tie ups since we left on July 4."
United States
Beth W.
The price is CA $182
CA $828 total
includes taxes & fees
Oct 5 - Oct 6
Coastal 2 Bedroom Duplex Steps Away from the Beach
A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

11. 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 $173
CA $666 total
includes taxes & fees
Oct 6 - Oct 7
Siesta beach....one and only
A staircase leading to a door with a welcome mat, a television on a stand, and a wooden ceiling.

12. 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 $111
CA $235 total
includes taxes & fees
Oct 8 - Oct 9
Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach
A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

13. 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 $145
CA $273 total
includes taxes & fees
Oct 19 - Oct 20
Sea Turtle- Full Sized living at Tiny House Siesta
A coastal resort with beachfront properties, a marina, and a distant city skyline.

14. Mimosa | Heated Pool + 0.2 Miles to Siesta Key Beach

Mimosa | Heated Pool + 0.2 Miles to Siesta Key Beach
Siesta Key Village
8.8 out of 10, Excellent, (15 reviews)
"Nice place! Would stay here again. Perfect location. "
United States
Laura
The price is CA $403
CA $1,003 total
includes taxes & fees
Oct 29 - Oct 30
Mimosa | Heated Pool + 0.2 Miles to Siesta Key Beach
A modern kitchen with white cabinetry, stainless steel appliances, and a tiled backsplash.

15. 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 $284
CA $1,224 total
includes taxes & fees
Oct 5 - Oct 6
Condo with Private Beach Access, Great Shared Amenities - Private Beach House
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

16. Lulu's Key House Leatherback 2/2 Downstairs

Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
Siesta Key Village
The price is CA $386
CA $955 total
includes taxes & fees
Oct 10 - Oct 11
Lulu's Key House Leatherback 2/2 Downstairs
An aerial view of a beach with clear turquoise waters, a sandy shore, and a coastal town with buildings and greenery.

17. Sea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (29 reviews)
"Perfect location and was very clean and updated"
United States
George J.
The price is CA $477
CA $921 total
includes taxes & fees
Oct 18 - Oct 19
Sea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
A beach with clear turquoise water, people swimming and walking along the shore, and a sailboat in the distance.

18. 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 $291
CA $833 total
includes taxes & fees
Oct 5 - Oct 6
Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
A pool area with a mural of a shark, two pools, hot tubs, and beach access.

19. Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool

Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool
Siesta Key Village
8.8 out of 10, Excellent, (13 reviews)
"Nice place for a quick each stay"
United States
M L.
The price is CA $266
CA $746 total
includes taxes & fees
Oct 5 - Oct 6
Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool
A sandy beach with a clear sky and palm trees.

20. 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 $205
CA $943 total
includes taxes & fees
Oct 5 - Oct 6
FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West
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

The Inn On Siesta Key

The Inn On Siesta Key

10/10 Excellent
"The room was very clean and modern. It is in walking distance to bars, shops, and restaurants. The staff was wonderful. We will definitely go back again."
Rick 4-night trip
Posted 22 hours ago
The Inn On Siesta Key

Find out more about Siesta Key

Siesta Key Vacation Homes information

Number of reviews
401
Accommodation
901 Vacation Homes
Lowest Price
CA $235
Highest Price
CA $1,224

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