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

Sarasota Holiday Rentals

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Our top choices for Sarasota holiday rentals

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,904 reviews)
"Loved our stay! Definitely recommend"
United States
Alexander
The price is NZ$312
includes taxes & fees
27 Sept - 28 Sept
Tropical Beach Resorts

2. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,450 reviews)
"This place was perfect!"
United States
Kat
The price is NZ$235
includes taxes & fees
22 Sept - 23 Sept
Hibiscus Suites - Gateway to Siesta Key

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,308 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is NZ$335
includes taxes & fees
22 Sept - 23 Sept
Captiva Beach Resort

4. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (181 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
The price is NZ$412
includes taxes & fees
22 Sept - 23 Sept
SeaSpray Resort

5. Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (467 reviews)
"Great place to stay,"
United States
Wilson
The price is NZ$326
includes taxes & fees
23 Sept - 24 Sept
Pelican Post at Anna Maria Island Inn

6. Siesta Vibe Pool Walk To Crescent Beach

Siesta Vibe Pool Walk To Crescent Beach
2.0 star property
South Village
The price is NZ$682
includes taxes & fees
22 Sept - 23 Sept
Siesta Vibe Pool Walk To Crescent Beach

7. [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 NZ$682
includes taxes & fees
19 Oct - 20 Oct
[escape to paradise] siesta key beach getaway

8. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
10.0 out of 10, Exceptional, (12 reviews)
"Very nice location. "
United States
Daniel o.
The price is NZ$419
includes taxes & fees
22 Sept - 23 Sept
Cozy Private Cottage, Minutes to Anna Maria Island

9. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (830 reviews)
"I loved this hotel"
United States
Raisare
The price is NZ$620
includes taxes & fees
23 Sept - 24 Sept
Bridgewalk Resort

10. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (681 reviews)
"Great stay!!"
United States
Genghis
The price is NZ$373
includes taxes & fees
7 Oct - 8 Oct
A Beach Retreat

11. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
The price is NZ$547
includes taxes & fees
1 Oct - 2 Oct
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

12. Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.4 out of 10, Exceptional, (8 reviews)
"I would stay again, very accommodating"
United States
Deliondra
The price is NZ$796
includes taxes & fees
22 Sept - 23 Sept
Cedar Run Resort - Roam Hospitality

13. 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 NZ$799
includes taxes & fees
22 Sept - 23 Sept
Siesta beach....one and only

14. Beautiful Resort Retreat Near Anna Maria Island & IMG w/ Heated Pools & Hot Tubs

Beautiful Resort Retreat Near Anna Maria Island & IMG w/ Heated Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (161 reviews)
"Good location, good communication with host, very clean. Very easy check in and check out process "
United States
Cathleen R.
The price is NZ$529
includes taxes & fees
22 Sept - 23 Sept
Beautiful Resort Retreat Near Anna Maria Island & IMG w/ Heated Pools & Hot Tubs

15. 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
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

16. Siesta Cooler: Only Minutes Walk to Siesta Beach!

Siesta Cooler: Only Minutes Walk to Siesta Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (75 reviews)
"great location- clean "
United States
Jon W.
The price is NZ$678
includes taxes & fees
23 Sept - 24 Sept
Siesta Cooler: Only Minutes Walk to Siesta Beach!

17. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (75 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is NZ$363
includes taxes & fees
26 Sept - 27 Sept
The "Grouper"

18. Stunning Waterfront Escape Near Anna Maria Island & IMG w/ Two Pools & Hot Tubs

Stunning Waterfront Escape Near Anna Maria Island & IMG w/ Two Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (125 reviews)
"We loved the property, large pool & access to activities. "
United States
Mary Beth M.
The price is NZ$534
includes taxes & fees
22 Sept - 23 Sept
Stunning Waterfront Escape Near Anna Maria Island & IMG w/ Two Pools & Hot Tubs

19. Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA
Longboat Key
9.2 out of 10, Wonderful, (140 reviews)
"We loved it and recommend it and definitely plan another. Locals only lol."
United States
Kenneth
The price is NZ$550
includes taxes & fees
22 Sept - 23 Sept
Oceanfront Oasis – Longboat Key 226 by RVA

20. Beachside Studio Located Across from Main Beach and Half Mile to Village

Beachside Studio Located Across from Main Beach and Half Mile to Village
Sarasota
8.8 out of 10, Excellent, (170 reviews)
"The rental had everything promised. The bed and couch were very comfortable. Everything was clean. Beach access was great. The chairs, cooler, and canopy were were just what was needed to maximize our enjoyment on a great beach."
United States
Karen G.
Beachside Studio Located Across from Main Beach and Half Mile to Village
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

Find out more about Sarasota

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Sarasota holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Sarasota. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Sarasota. Seeing all the best attractions is bound to make you fall in love with Sarasota. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Sarasota short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there holiday rentals in Sarasota?

Yes, there are holiday rentals in Sarasota close to Marie Selby Botanical Gardens, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Sarasota like the popular beaches and fascinating museums this destination is known for. While you're in the area, you can also enjoy the picturesque gardens and entertainment choices.

What are some of the best holiday rentals that Sarasota has to offer?

BEAUTIFULL VACATION HOUSE: This highly rated holiday home rental in Sarasota is located by the ocean, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Other favourite homes for rent in Sarasota are Downtown,Italian Villa For Two,Resort Style.5 minutes to Siesta-Lido. and Tamiami Vice - Luxury Siesta Key Home with Heated Pool & Prime Location – Book Your Escape Today!.

How many holiday rentals are there in Sarasota?

With 322 Expedia holiday rentals, you're guaranteed to find just the right place for your Sarasota stay.

What’s there to see and do in Sarasota?

Enjoy the outdoors at Lido Beach and Marie Selby Botanical Gardens, or simply take in cultural attractions like Sarasota Opera House and John and Mable Ringling Museum of Art. Marina Jack and Van Wezel Performing Arts Hall are other places to visit while you're in town.

What’s a holiday rental in Sarasota like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sarasota. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family gatherings.