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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Siesta Key vacation homes

5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

1. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (80 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is ￥15,754
￥51,255 total
includes taxes & fees
Aug 31 - Sep 1
Siesta Key Island Rentals
Private kitchen

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)
"Thanks for a great stay, Jayme! Perfect location and extremely accurate Vrbo listing! Beds super comfy!"
United States
Sue H.
The price is ￥13,027
￥46,731 total
includes taxes & fees
Sep 7 - Sep 8
[lounge like locals] walk to siesta beach +bikes
House, Lakeside | Living area

3. 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 ￥15,707
￥49,951 total
includes taxes & fees
Sep 2 - Sep 3
Siesta Heron Suites & Villas
Beach

4. 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 ￥17,770
￥32,647 total
includes taxes & fees
Aug 31 - Sep 1
The Mermaid at Tiny House Siesta
Property grounds

5. 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 ￥14,728
￥60,975 total
includes taxes & fees
Aug 31 - Sep 1
Island Villa | Cozy Beach Retreat | Walk to Village
Outdoor dining

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 ￥16,569
￥57,952 total
includes taxes & fees
Sep 7 - Sep 8
Dolphin Villa - Pool - Steps to Siesta Key Village
Outdoor dining

7. 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 ￥20,251
￥68,073 total
includes taxes & fees
Sep 9 - Sep 10
Everglades Villa • Sleeps 8 • Walk to Siesta Beach
Villa, Pets Allowed, Beach View | Pool

8. DOLPHIN PRIVATE HOUSE

DOLPHIN PRIVATE HOUSE
3.0 star property
Siesta Key Village
The price is ￥85,003
￥96,053 total
includes taxes & fees
Aug 31 - Sep 1
DOLPHIN PRIVATE HOUSE
Living area

9. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (218 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 ￥19,451
￥74,786 total
includes taxes & fees
Sep 8 - Sep 9
Siesta beach....one and only
Exterior

10. 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 ￥19,883
￥66,171 total
includes taxes & fees
Aug 31 - Sep 1
2 Bedroom Unit with Pool - 2 min walk to Siesta Beach
Beach

11. 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 ￥22,843
￥98,105 total
includes taxes & fees
Aug 31 - Sep 1
Siesta Key Beach Duplex-Close to Sarasota Beach/Pet Friendly
Private kitchen

12. Summer Salt – Steps to Siesta Key Village & Beach

Summer Salt – Steps to Siesta Key Village & Beach
Siesta Key Village
10.0 out of 10, Exceptional, (2 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 ￥22,121
￥79,187 total
includes taxes & fees
Sep 8 - Sep 9
Summer Salt – Steps to Siesta Key Village & Beach
Property grounds

13. 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, (5 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 ￥22,121
￥91,322 total
includes taxes & fees
Sep 7 - Sep 8
Salty Summer – Steps to Siesta Key Village & Beach
Condo (LuLu's Key House Green 1/1 Upstairs) | Exterior

14. Lulu's Key House Green 1/1 Upstairs

Lulu's Key House Green 1/1 Upstairs
3.5 star property
Siesta Key Village
Lulu's Key House Green 1/1 Upstairs
Interior

15. 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 ￥22,693
￥96,254 total
includes taxes & fees
Aug 31 - Sep 1
Beautiful 2 Bedroom Duplex Steps Away from the Beach
Pool

16. 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 ￥41,423
￥97,438 total
includes taxes & fees
Sep 27 - Sep 28
Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool
Pool

17. 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 ￥24,494
￥68,829 total
includes taxes & fees
Sep 12 - Sep 13
Modern 2BR Retreat · Heated Pool · Near Siesta
Beach

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 ￥34,407
￥95,736 total
includes taxes & fees
Aug 31 - Sep 1
Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
Beach

19. 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 ￥25,304
￥105,525 total
includes taxes & fees
Aug 31 - Sep 1
FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West
Private kitchen

20. 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, (49 reviews)
"Perfect spot for beach vacation "
United States
Megan C.
The price is ￥35,037
￥141,839 total
includes taxes & fees
Aug 31 - Sep 1
Condo with Private Beach Access, Great Shared Amenities - Private Beach House
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

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"N/A"
Silvia 1-night trip
Posted less than an hour ago
Tropical Beach Resorts

Find out more about Siesta Key

Siesta Key Vacation Homes information

Number of reviews
381
Accommodation
900 Vacation Homes
Lowest Price
￥32,647
Highest Price
￥141,839