A beach with a wooden pier extending into the turquoise sea, palm trees, and people walking on the pier.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Sarasota vacation homes

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.

1. 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 ￥15,474
￥49,271 total
includes taxes & fees
Oct 19 - Oct 20
Siesta Heron Suites & Villas
A modern kitchen with a central island, bar stools, a window, and a dark cabinet.

2. Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
The Meadows
10.0 out of 10, Exceptional, (29 reviews)
"The perfect place and the best rental I’ve stayed in!! All the descriptions are perfect. If you’re looking for a private getaway that’s close and cozy, this is it."
United States
Emma
The price is ￥14,392
￥36,124 total
includes taxes & fees
Oct 21 - Oct 22
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
A modern bedroom with a bed, a bedside table, a round dining table with chairs, and a large window with curtains.

3. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (34 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 ￥14,486
￥48,302 total
includes taxes & fees
Oct 19 - Oct 20
[escape to paradise] siesta key beach getaway
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

4. 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 ￥19,263
￥60,833 total
includes taxes & fees
Oct 31 - Nov 1
Dolphin Villa | Pool | Steps to Siesta Key Village
A modern living room with a blue sofa, a dining table with chairs, a woven rug, and a kitchen area in the background.

5. Lobster Louie's Inn - Cozy 2/1 Mins from Beaches. Fenced yard. Pet Friendly.

Lobster Louie's Inn - Cozy 2/1 Mins from Beaches. Fenced yard. Pet Friendly.
Whitfield Estates
9.0 out of 10, Wonderful, (26 reviews)
"The host was excellent and made sure that we had a great stay. The place was very clean and extremely nice. My family and I had a wonderful time."
United States
Anonymous traveler
The price is ￥12,231
￥47,288 total
includes taxes & fees
Oct 19 - Oct 20
Lobster Louie's Inn - Cozy 2/1 Mins from Beaches. Fenced yard. Pet Friendly.
A wooden beach pavilion with a checkered roof and open sides, overlooking the beach.

6. Anna Maria Beach Condo 1/1

Anna Maria Beach Condo 1/1
Bradenton Beach
9.8 out of 10, Exceptional, (237 reviews)
"Great place to stay!"
United States
Donna B.
The price is ￥22,755
￥57,191 total
includes taxes & fees
Oct 19 - Oct 20
Anna Maria Beach Condo 1/1
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 ￥13,748
￥27,624 total
includes taxes & fees
Oct 20 - Oct 21
The Mermaid at Tiny House Siesta
A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

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 ￥16,355
￥62,260 total
includes taxes & fees
Oct 20 - Oct 21
Island Villa | Cozy Beach Retreat | Walk to Village
A balcony with two blue chairs and a small table, overlooking a lake with trees and a sunset.

9. Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Sabal Harbour
10.0 out of 10, Exceptional, (35 reviews)
"Great location! I loved the sunsets on the back patio!"
United States
Megan R.
The price is ￥17,066
￥51,442 total
includes taxes & fees
Oct 25 - Oct 26
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

10. 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 ￥20,898
￥68,386 total
includes taxes & fees
Oct 19 - Oct 20
Everglades Villa • Sleeps 8 • Walk to Siesta Beach
A modern kitchen with white cabinetry, a stainless steel refrigerator, a marble backsplash, and a central island with two stools.

11. Lovely House in Sarasota, close to UTC Mall, Nathan B Park, and Siesta Key Beach

Lovely House in Sarasota, close to UTC Mall, Nathan B Park, and Siesta Key Beach
Sarasota
10.0 out of 10, Exceptional, (6 reviews)
"House was charming, clean and comfortable - neighborhood was quiet. "
United States
Mary I. O.
The price is ￥22,123
￥81,586 total
includes taxes & fees
Oct 19 - Oct 20
Lovely House in Sarasota, close to UTC Mall, Nathan B Park, and Siesta Key Beach
A beachside restaurant with outdoor seating, palm trees, and a thatched-roof structure.

12. Luxury Family Home Near Downtown & Siesta Key Beach

Luxury Family Home Near Downtown & Siesta Key Beach
Alta Vista
9.8 out of 10, Exceptional, (82 reviews)
"Excellent property at a great value. Very clean and centrally located. "
United States
Joseph C.
The price is ￥17,919
￥56,449 total
includes taxes & fees
Oct 20 - Oct 21
Luxury Family Home Near Downtown & Siesta Key Beach
A house with a porch, number 203, and a ceiling fan.

13. The Hideaways at Point Pleasant (Pine Side)

The Hideaways at Point Pleasant (Pine Side)
Bradenton
9.8 out of 10, Exceptional, (182 reviews)
"Great location and wonderful place to stay."
United States
Theresa H.
The price is ￥17,224
￥47,175 total
includes taxes & fees
Oct 19 - Oct 20
The Hideaways at Point Pleasant (Pine Side)
A dining table set with plates, glasses, and a decorative glass holder.

14. Beachside Bliss: Family House-Siesta Key-3BR/2BA

Beachside Bliss: Family House-Siesta Key-3BR/2BA
Sarasota
10.0 out of 10, Exceptional, (28 reviews)
"Very clean and tucked away in a quiet little neighborhood with everything you need within 10 mins...this place made for the most comfortable and perfect vacation!"
United States
christy v.
The price is ￥16,071
￥54,362 total
includes taxes & fees
Oct 28 - Oct 29
Beachside Bliss: Family House-Siesta Key-3BR/2BA
A kitchen with white cabinets, a granite countertop, stainless steel appliances, and a tiled backsplash.

15. Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (84 reviews)
"The place was super cute, clean, quiet, cozy, and in a great location. The host was very communicative and sweet. Definitely a great stay, 10/10 recommend!"
United States
Sierra B.
The price is ￥25,125
￥56,084 total
includes taxes & fees
Nov 8 - Nov 9
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
A swimming pool with a surrounding garden and a covered area with a metal roof.

16. Backyard Oasis & Resort Style Pool

Backyard Oasis & Resort Style Pool
Bradenton
10.0 out of 10, Exceptional, (70 reviews)
"Great house! Super clean and amazing pool area. Would stay again!"
United States
Katina M.
The price is ￥19,468
￥69,285 total
includes taxes & fees
Oct 19 - Oct 20
Backyard Oasis & Resort Style Pool
A beach with clear turquoise water, a sandy shore, and a few beach umbrellas.

17. 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 ￥16,118
￥30,618 total
includes taxes & fees
Oct 22 - Oct 23
Sea Turtle- Full Sized living at Tiny House Siesta
A lifeguard tower with a blue umbrella on a sandy beach.

18. Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA

Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA
Bradenton
10.0 out of 10, Exceptional, (15 reviews)
"Great spot, lovely back yard and pool, so relaxing we loved it."
United States
Cadence
The price is ￥12,918
￥58,677 total
includes taxes & fees
Oct 29 - Oct 30
Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA
A beachside restaurant with a thatched roof, wooden tables, and chairs, overlooking a sandy beach and the ocean.

19. LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access

LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
Sunny Shores
9.6 out of 10, Exceptional, (44 reviews)
"Superb value, quiet area, responsive owner, very nicely appointed; will definitely book again for next visit to Anna Maria Island!"
United States
Bryce W.
The price is ￥12,721
￥74,606 total
includes taxes & fees
Oct 23 - Oct 24
LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
A covered patio with a round table and chairs, large windows, and a view of a backyard with a wooden fence and palm trees.

20. 2 miles to #1 Beach Siesta Key

2 miles to #1 Beach Siesta Key
Sarasota
9.8 out of 10, Exceptional, (85 reviews)
"Clean and convenient"
United States
Scott H.
2 miles to #1 Beach Siesta Key
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 Sarasota Hotel Reviews

Carlisle Inn

Carlisle Inn

10/10 Excellent
"I enjoyed my stay. The catered dinner was excellent. Compliments to the chef. The room was clean and fresh smelling."
Jacqueline 1-night trip
Posted 2 hours ago
Carlisle Inn

Find out more about Sarasota

Sarasota Vacation Homes information

Number of reviews
784
Accommodation
5490 Vacation Homes
Lowest Price
￥27,624
Highest Price
￥81,586