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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Sarasota holiday homes

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

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 £242
includes taxes & fees
30 Sept - 1 Oct
Siesta Key Island Rentals
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.

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 £222
includes taxes & fees
23 Sept - 24 Sept
Siesta Heron Suites & Villas
A modern kitchen with white cabinets, a stainless steel microwave, an oven, and a coffee maker.

3. Charming 2-bedroom house in lovely Sarasota with yard.

Charming 2-bedroom house in lovely Sarasota with yard.
Kensington Park
9.4 out of 10, Exceptional, (36 reviews)
"My husband and I really enjoyed our stay at this home. It was clean, nicely decorated, and had everything we needed. The host was very responsive and friendly. The neighborhood was quiet and nice. The AC works well."
United States
Julie B.
The price is £178
includes taxes & fees
26 Sept - 27 Sept
Charming 2-bedroom house in lovely Sarasota with yard.
A beach with waves and a bird flying near the shore.

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 £125
includes taxes & fees
27 Sept - 28 Sept
The Mermaid at Tiny House Siesta
A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

5. [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 £223
includes taxes & fees
27 Sept - 28 Sept
[lounge like locals] walk to siesta beach +bikes
A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

6. 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 £333
includes taxes & fees
30 Sept - 1 Oct
Siesta beach....one and only
A balcony with two blue chairs and a small table, overlooking a lake with trees and a sunset.

7. 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, (34 reviews)
"Great location! I loved the sunsets on the back patio!"
United States
Megan R.
The price is £243
includes taxes & fees
27 Sept - 28 Sept
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
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 £290
includes taxes & fees
23 Sept - 24 Sept
Island Villa | Cozy Beach Retreat | Walk to Village
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

9. 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 £276
includes taxes & fees
29 Sept - 30 Sept
Dolphin Villa - Pool - Steps to Siesta Key Village
A lifeguard tower with a blue umbrella on a sandy beach.

10. 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, (14 reviews)
"Great spot, lovely back yard and pool, so relaxing we loved it."
United States
Cadence
The price is £292
includes taxes & fees
29 Sept - 30 Sept
Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA
A swimming pool with a surrounding garden and a covered area with a metal roof.

11. Backyard Oasis & Resort Style Pool

Backyard Oasis & Resort Style Pool
Bradenton
10.0 out of 10, Exceptional, (67 reviews)
"Great house! Super clean and amazing pool area. Would stay again!"
United States
Katina M.
The price is £327
includes taxes & fees
23 Sept - 24 Sept
Backyard Oasis & Resort Style Pool
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

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 £313
includes taxes & fees
23 Sept - 24 Sept
Everglades Villa • Sleeps 8 • Walk to Siesta Beach
A dining table set with plates, glasses, and a decorative glass holder.

13. 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)
"Great property! Very clean and spacious. Perfect for what we needed and close to Siesta Key and Gulf Gate restaurants and bars,"
United States
Lori B.
The price is £256
includes taxes & fees
27 Sept - 28 Sept
Beachside Bliss: Family House-Siesta Key-3BR/2BA
A sandy pathway leading to a beach, flanked by green foliage and rope barriers.

14. Modern Coastal Charm • Near AMI Beach-IMG Academy

Modern Coastal Charm • Near AMI Beach-IMG Academy
Bradenton
10.0 out of 10, Exceptional, (41 reviews)
"Very cute 2 bedroom place with parking, Wi-fi, private fenced outdoor space. Safe location convenient drive to the beach. Would stay there again."
United States
Dawn Z.
The price is £226
includes taxes & fees
24 Sept - 25 Sept
Modern Coastal Charm • Near AMI Beach-IMG Academy
A beach with clear turquoise water, white sand, and a row of trees and buildings along the shore.

15. IMG Lake & Beach Home Pool White Sand Beaches SEPTEMBER, Oct, Nov, Dec SPECIALS!

IMG Lake & Beach Home Pool White Sand Beaches SEPTEMBER, Oct, Nov, Dec SPECIALS!
South Bradenton
9.8 out of 10, Exceptional, (140 reviews)
"Beautiful pool, nice kitchen, and close to Anna Marie Island."
United States
Gary B.
The price is £381
includes taxes & fees
23 Sept - 24 Sept
IMG Lake & Beach Home Pool White Sand Beaches SEPTEMBER, Oct, Nov, Dec SPECIALS!
A modern kitchen with a central island, bar stools, a window, and a dark cabinet.

16. 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, (27 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 £183
includes taxes & fees
27 Sept - 28 Sept
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
A dining area with a dark wooden table, four chairs, and a hanging lamp.

17. Lakeview Bradenton Rental Near Beaches & IMG

Lakeview Bradenton Rental Near Beaches & IMG
South Bradenton
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and comfortable. "
United States
Dee F.
The price is £177
includes taxes & fees
27 Sept - 28 Sept
Lakeview Bradenton Rental Near Beaches & IMG
A beachside restaurant with a thatched roof, wooden tables, and chairs, overlooking a sandy beach and the ocean.

18. 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 £351
includes taxes & fees
30 Sept - 1 Oct
LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
An aerial view of a coastal area with a long sandy beach, a clear blue sea, and a densely populated residential area with houses and buildings.

19. 1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!
River District
10.0 out of 10, Exceptional, (80 reviews)
"Awesome cozy home in a very nice, quiet neighborhood!"
United States
Percy L.
The price is £249
includes taxes & fees
23 Sept - 24 Sept
1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!
A covered swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.

20. "Stingray" 3 miles to Anna Marie

"Stingray" 3 miles to Anna Marie
Bradenton
9.8 out of 10, Exceptional, (36 reviews)
"Property was great and location was ideal for our weekend getaway"
United States
Agnieszka
The price is £227
includes taxes & fees
27 Sept - 28 Sept
"Stingray" 3 miles to Anna Marie
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
"Breakfast was just ok"
Paul 3-night trip
Posted 3 hours ago
Carlisle Inn

Find out more about Sarasota

Sarasota Holiday Homes information

Number of reviews
662
Accommodation
5488 Holiday Homes
Lowest Price
£125
Highest Price
£381