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Florida Holiday Rentals

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Our top choices for Florida holiday rentals

1. Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (55 reviews)
"Great location in the heart of Warwick, NY. Easy to walk around town and visit the local restaurants!"
United States
Francis
The price is NZ$430
includes taxes & fees
16 Nov - 17 Nov
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

2. Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.8 out of 10, Excellent, (23 reviews)
"Great place, but you can hear red everything going on outside your room with the restaurant downstairs and other people in the common area. But I’d definitely come back here"
United States
Joseph
The price is NZ$282
includes taxes & fees
16 Nov - 17 Nov
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

3. Columbus Suites

Columbus Suites
3.0 star property
Middletown
6.6 out of 10, (23 reviews)
"My worst experience ever staying at the hotel no communication locked out at the sleep in my car. I would never recommend anybody to stay there. The bed is horrible no curtains window basically nothing nice to say about that property. Sorry."
United States
Edwin
The price is NZ$260
includes taxes & fees
16 Nov - 17 Nov
Columbus Suites

4. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is NZ$504
includes taxes & fees
16 Nov - 17 Nov
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

5. The Columbus Hotel - The Atelier Suite - 52-303

The Columbus Hotel - The Atelier Suite - 52-303
Middletown
The price is NZ$334
includes taxes & fees
15 Dec - 16 Dec
The Columbus Hotel - The Atelier Suite - 52-303

6. The Columbus Hotel - Golden Hour Studio - 89-305

The Columbus Hotel - Golden Hour Studio - 89-305
Middletown
The price is NZ$253
includes taxes & fees
15 Nov - 16 Nov
The Columbus Hotel - Golden Hour Studio - 89-305

7. Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (49 reviews)
"Always a pleasure staying here."
United States
Natalie M.
The price is NZ$445
includes taxes & fees
29 Nov - 30 Nov
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

8. Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (69 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
The price is NZ$930
includes taxes & fees
18 Nov - 19 Nov
Country House w/Hot Tub, Deck, Grill & Fire Pit

9. The Wine House

The Wine House
Warwick
10.0 out of 10, Exceptional, (40 reviews)
"Amazing place - we will definitely be back ."
United States
Robin
The price is NZ$497
includes taxes & fees
15 Nov - 16 Nov
The Wine House

10. The Columbus Hotel - The Courtyard Suite - 89-303

The Columbus Hotel - The Courtyard Suite - 89-303
Middletown
The price is NZ$330
includes taxes & fees
14 Dec - 15 Dec
The Columbus Hotel - The Courtyard Suite - 89-303

11. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
United States
Scott
The price is NZ$976
includes taxes & fees
30 Nov - 1 Dec
Hudson Valley Retreat w/ Pool Near Greenwood Lake

12. Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (14 reviews)
"The breakfast was lovely!"
United States
Tara
The price is NZ$483
includes taxes & fees
15 Nov - 16 Nov
Villa Verde B&B, bsm, Greenwood Lake NY

13. Villa Verde B&B, Greenwood Lake NY, 1

Villa Verde B&B, Greenwood Lake NY, 1
Monroe
10.0 out of 10, Exceptional, (31 reviews)
"Great host. Home is very clean and well appointed. Would definitely stay here again."
United States
Thomas
The price is NZ$551
includes taxes & fees
15 Nov - 16 Nov
Villa Verde B&B, Greenwood Lake NY, 1

14. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.8 out of 10, Excellent, (28 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is NZ$280
includes taxes & fees
17 Nov - 18 Nov
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

15. Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Goshen
10.0 out of 10, Exceptional, (35 reviews)
"Great house, as advertised!"
United States
Steven K.
The price is NZ$1,206
includes taxes & fees
15 Nov - 16 Nov
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

16. Top of the tower penthouse suite in Village of Warwick

Top of the tower penthouse suite in Village of Warwick
Warwick
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful stay!"
United States
Lisi M.
The price is NZ$719
includes taxes & fees
17 Nov - 18 Nov
Top of the tower penthouse suite in Village of Warwick

17. Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8
Chester
8.8 out of 10, Excellent, (3 reviews)
"Thank you for the weekend. We had a great time and Sugarloaf was a great location for us all to catch up."
United States
Jeff S.
Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

18. Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Vernon Township
9.4 out of 10, Exceptional, (65 reviews)
"Really nice retreat , not far from NYC, place very clean , great pool ,"
United States
Jakub S.
The price is NZ$522
includes taxes & fees
25 Nov - 26 Nov
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

19. The Columbus Hotel - The District Studio - 89-204

The Columbus Hotel - The District Studio - 89-204
Middletown
The price is NZ$258
includes taxes & fees
15 Nov - 16 Nov
The Columbus Hotel - The District Studio - 89-204

20. The Columbus Hotel - The Residence Studio - 89-206

The Columbus Hotel - The Residence Studio - 89-206
Middletown
The price is NZ$285
includes taxes & fees
16 Nov - 17 Nov
The Columbus Hotel - The Residence Studio - 89-206
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 Florida Hotel Reviews

Find out more about Florida

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 Florida 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 Florida. 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 Florida. Seeing all the best attractions is bound to make you fall in love with Florida. 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 Florida short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Florida?

Yes, there are holiday rentals close to the most popular sights in Florida, or you can select a more secluded option if you're looking for a relaxing stay.

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

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Florida is located on a lake, 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.

What’s there to see and do in Florida?

While exploring the area, visit family-friendly sights like LEGOLAND® New York, or get outside and enjoy nature at The Rock Sports Complex. Woodbury Common Premium Outlets and Applewood Winery are a couple of places you'll find in the wider area.

What’s a holiday rental in Florida like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Florida. Holiday rentals offer amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for families.