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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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 $161
CA $527 total
includes taxes & fees
Oct 31 - Nov 1
Dolphin Villa | Pool | Steps to Siesta Key Village
A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

2. 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.
Island Villa | Cozy Beach Retreat | Walk to Village
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.

3. 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 $139
CA $439 total
includes taxes & fees
Nov 2 - Nov 3
Siesta Heron Suites & Villas
A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

4. [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 $102
CA $396 total
includes taxes & fees
Oct 28 - Oct 29
[lounge like locals] walk to siesta beach +bikes
A compact, well-lit interior with a bunk bed, seating area, kitchenette, and a television.

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 $245 total
includes taxes & fees
Oct 27 - Oct 28
The Mermaid at Tiny House Siesta
A covered patio with a ceiling fan, white chairs, and a glass table.

6. 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)
"Beautiful little place. Super clean. Has everything you need. Great communication and quick response to any need. Fast walk to the beach and village."
United States
Ivette R.
The price is CA $198
CA $856 total
includes taxes & fees
Oct 27 - Oct 28
Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly
A modern kitchen with a central island, a dining area with a table and chairs, and a living area with a sofa and a wall-mounted TV.

7. 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 $269 total
includes taxes & fees
Oct 27 - Oct 28
Sea Turtle- Full Sized living at Tiny House Siesta
A staircase leading to a door with a welcome mat, a television on a stand, and a wooden ceiling.

8. 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 $109
CA $231 total
includes taxes & fees
Oct 27 - Oct 28
Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach
A modern kitchen with a stainless steel refrigerator, granite countertop, white cabinetry, and a dining area with a table and chairs.

9. 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 $213
CA $862 total
includes taxes & fees
Oct 30 - Oct 31
Beautiful 2 Bedroom Duplex Steps Away from the Beach
A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

10. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (222 reviews)
"Nice stay perfect location"
United States
tom f.
The price is CA $183
CA $670 total
includes taxes & fees
Nov 9 - Nov 10
Siesta beach....one and only
A residential area with houses, palm trees, and a view of the ocean.

11. 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 $234
CA $901 total
includes taxes & fees
Oct 27 - Oct 28
Pet Friendly home, Close to Sarasota Beach!
A deck with a mural of a sea turtle and boats, a hot tub, and outdoor seating.

12. 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 $246
CA $714 total
includes taxes & fees
Oct 28 - Oct 29
Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool
A modern kitchen with white cabinetry, stainless steel appliances, and a tiled backsplash.

13. 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 $279
CA $1,203 total
includes taxes & fees
Oct 27 - Oct 28
Condo with Private Beach Access, Great Shared Amenities - Private Beach House
A covered outdoor seating area with wooden furniture and a thatched roof.

14. Sea Coast - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Coast - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (40 reviews)
"Great property for couples. We would definitely stay again."
United States
Kellie O.
The price is CA $502
CA $950 total
includes taxes & fees
Oct 31 - Nov 1
Sea Coast - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Living area

15. Unique & Artsy Beach Getaway: Pool ~ Hot Tub ~ Pkg

Unique & Artsy Beach Getaway: Pool ~ Hot Tub ~ Pkg
Siesta Key Village
8.0 out of 10, Very good, (5 reviews)
"Great location got a little loud with upstairs guest dog running across floors. "
United States
Jessica W.
The price is CA $239
CA $706 total
includes taxes & fees
Oct 27 - Oct 28
Unique & Artsy Beach Getaway: Pool ~ Hot Tub ~ Pkg
A poolside setting with candles and decorative stones.

16. 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 $179
CA $558 total
includes taxes & fees
Oct 29 - Oct 30
Modern 2BR Retreat · Heated Pool · Near Siesta
An aerial view of a coastal area with a beach, buildings, and a clear blue sky.

17. 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)
"The location is unmatched!!! It was the perfect size for us. The kitchen was well stocked with all the cooking equipment needed. We will definitely be back. Great memories made"
United States
Melissa H.
The price is CA $347
CA $923 total
includes taxes & fees
Oct 27 - Oct 28
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
A swimming pool with a mural of a flamingo and a swan on the building.

18. 2 Bedroom Unit with Pool - 2 min walk to Siesta Beach

2 Bedroom Unit with Pool - 2 min walk to Siesta Beach
Siesta Key
10.0 out of 10, Exceptional, (2 reviews)
"My husband, parents and I only stayed for three nights, but it was an absolute perfect spot for us! Very close to the beach and trolley stops to get you pretty much anywhere on Siesta Key. The place was very clean and adorably decorated. The pool and hot tub were exactly as described and made our trip even better. We Would definitely stay here again!"
United States
Melissa B.
The price is CA $341
CA $790 total
includes taxes & fees
Nov 1 - Nov 2
2 Bedroom Unit with Pool - 2 min walk to Siesta Beach
A modern kitchen with stainless steel appliances, wooden cabinets, and a granite countertop.

19. Summer Salt ~ Near Village ~ Shared Pool

Summer Salt ~ Near Village ~ Shared Pool
Siesta Key Village
10.0 out of 10, Exceptional, (3 reviews)
"This is the second year my family and I have stayed here and it was lovely! The distance to the village shops and restaurants was perfect and it is just a small walk away from the beach. The host was also very attentive and replied quickly to our messages. Everything was very clean and comfortable!"
United States
Brook M.
The price is CA $313
CA $836 total
includes taxes & fees
Nov 15 - Nov 16
Summer Salt ~ Near Village ~ Shared Pool
A covered balcony with wicker furniture, a ceiling fan, and lush tropical plants.

20. Salty Summer ~ Near Village ~ Shared Pool

Salty Summer ~ Near Village ~ Shared Pool
Siesta Key Village
10.0 out of 10, Exceptional, (6 reviews)
"Very nice and well located property"
United States
George
The price is CA $306
CA $943 total
includes taxes & fees
Nov 1 - Nov 2
Salty Summer ~ Near Village ~ Shared Pool
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

Siesta Key Beachside Villas

Siesta Key Beachside Villas

8/10 Good
"Fantastic location!! Cute resort, provide everything you need."
Shanna 4-night trip
Posted 1 day ago
Siesta Key Beachside Villas

Find out more about Siesta Key

Siesta Key Vacation Homes information

Number of reviews
469
Accommodation
873 Vacation Homes
Lowest Price
CA $231
Highest Price
CA $1,203

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