Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Windsor vacation rentals

View from property

Yearling Restaurant and Cabins

Yearling Restaurant and Cabins
2.5 star property
Hawthorne
9.2 out of 10, Wonderful, (199 reviews)
"I stayed for one night and was happy with my cabin. It was clean and comfortable. The staff was friendly and welcoming, the check in process uncomplicated."
United States
Gabriele
The price is ￥21,514
￥24,204 total
includes taxes & fees
Feb 4 - Feb 5
Yearling Restaurant and Cabins
Property grounds

White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing

White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing
Keystone Heights
9.6 out of 10, Exceptional, (14 reviews)
"Awesome location, great cabin! Had everything I needed to see my family ❤️ Will request to stay again!"
United States
Bonnie
The price is ￥10,587
￥28,065 total
includes taxes & fees
Feb 4 - Feb 5
White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing
Terrace/patio

Palmetto Cottage-1930’s Florida Cottage

Palmetto Cottage-1930’s Florida Cottage
Micanopy
9.8 out of 10, Exceptional, (48 reviews)
"House was interesting and comfortable, location was perfect and I fell in love with Micanopy.."
United States
Robin
The price is ￥16,871
￥35,624 total
includes taxes & fees
Feb 8 - Feb 9
Palmetto Cottage-1930’s Florida Cottage
Exterior

"La Grande" Retro Escape

"La Grande" Retro Escape
Gainesville
10.0 out of 10, Exceptional, (4 reviews)
"The host was very accommodating. Sweet place. "
United States
Deanne H.
The price is ￥12,228
￥23,818 total
includes taxes & fees
Feb 4 - Feb 5
"La Grande" Retro Escape
House (2 Bedrooms) | Interior

Hawthorne Angler's Cabin w/ Lake + Dock Access!

Hawthorne Angler's Cabin w/ Lake + Dock Access!
3.0 star property
Hawthorne
The price is ￥26,467
￥55,337 total
includes taxes & fees
Feb 4 - Feb 5
Hawthorne Angler's Cabin w/ Lake + Dock Access!
Exterior

Juniper Cottage — In the Heart of Old Florida

Juniper Cottage — In the Heart of Old Florida
Micanopy
9.4 out of 10, Exceptional, (16 reviews)
"We stayed one night - the home was perfect. Sweet decor/furnishings, lovely old cottage nestled in the trees. The bed was comfy & we appreciated the coffee in the morning. We liked it so much that we're going to stay again in a couple of weeks!"
United States
Pamela S.
Juniper Cottage — In the Heart of Old Florida
Property grounds

Charming 1-bedroom house with AC, WiFi in welcoming Melrose

Charming 1-bedroom house with AC, WiFi in welcoming Melrose
Melrose
10.0 out of 10, Exceptional, (1 review)
"Was a great place to unwind after a long day at work. Very relaxing, very quiet"
United States
Matthew g.
The price is ￥14,395
￥22,510 total
includes taxes & fees
Feb 22 - Feb 23
Charming 1-bedroom house with AC, WiFi in welcoming Melrose
Exterior

The Nest: Cozy 1-bedroom apartment in fabulous Gainesville with pickleball!

The Nest: Cozy 1-bedroom apartment in fabulous Gainesville with pickleball!
Gainesville
9.4 out of 10, Exceptional, (6 reviews)
"Neat, clean, comfortable, well priced, secure location & property."
United States
Richard P.
The price is ￥11,144
￥27,822 total
includes taxes & fees
Feb 8 - Feb 9
The Nest: Cozy 1-bedroom apartment in fabulous Gainesville with pickleball!
Exterior

Go Gators Apartment + PS4 Console!

Go Gators Apartment + PS4 Console!
Gainesville
9.6 out of 10, Exceptional, (5 reviews)
"Host was great with communication, condo was clean, well stocked and we enjoyed it."
United States
Kelly B.
The price is ￥9,751
￥28,789 total
includes taxes & fees
Feb 8 - Feb 9
Go Gators Apartment + PS4 Console!
Property grounds

La Casita: Charming 1-bedroom house in Gainesville w/ pickleball court!

La Casita: Charming 1-bedroom house in Gainesville w/ pickleball court!
Gainesville
10.0 out of 10, Exceptional, (5 reviews)
"This property was just what we needed for a place to stay after going to the UF game. Easy to find and located close enough to campus (not walking distamce though) for us. It was a quick turnarpund for us, but if we need to stay another time longer i would definitely want to stay here again."
United States
Christi R.
The price is ￥13,234
￥28,432 total
includes taxes & fees
Feb 8 - Feb 9
La Casita: Charming 1-bedroom house in Gainesville w/ pickleball court!
Interior

Expansive Forest Ridge Retreat in Central GNV

Expansive Forest Ridge Retreat in Central GNV
Gainesville
9.8 out of 10, Exceptional, (6 reviews)
"Our stay was amazing! Great location close to the cancer center which was the reason we needed a place for 5 weeks. It was 3 adult and 2 small pups and the place felt like home away from home. We highly recommend it! "
United States
Yolanda B.
The price is ￥11,376
￥48,070 total
includes taxes & fees
Feb 4 - Feb 5
Expansive Forest Ridge Retreat in Central GNV
Living area

Modern & Stylish Condo Near UF - Foxmoor

Modern & Stylish Condo Near UF - Foxmoor
Gainesville
9.6 out of 10, Exceptional, (5 reviews)
"Very responsive host and the property was clean and well stocked."
United States
C I.
The price is ￥11,539
￥43,280 total
includes taxes & fees
Feb 9 - Feb 10
Modern & Stylish Condo Near UF - Foxmoor
Fridge, microwave, oven, stovetop

Harmons Landing charming 2 bedroom cabin Cross Creek

Harmons Landing charming 2 bedroom cabin Cross Creek
Hawthorne
10.0 out of 10, Exceptional, (4 reviews)
"What a hidden gem! We went for a getaway to explore orange lake and lake lochloosa. The accommodations were perfect for just that. "
United States
Barry S.
The price is ￥24,378
￥45,999 total
includes taxes & fees
Feb 4 - Feb 5
Harmons Landing charming 2 bedroom cabin Cross Creek
1 bedroom, iron/ironing board, WiFi, bed sheets

Private suite with own entry in vibrant Gainesville

Private suite with own entry in vibrant Gainesville
Gainesville
10.0 out of 10, Exceptional, (7 reviews)
"A great location and a great space. Very quiet house and a great bed! Highly recommend. "
United States
Valrie D.
The price is ￥9,287
￥22,250 total
includes taxes & fees
Feb 4 - Feb 5
Private suite with own entry in vibrant Gainesville
House (1 Bedroom) | Interior

Bass Fishing Paradise w/ Shared Dock in Hawthorne!

Bass Fishing Paradise w/ Shared Dock in Hawthorne!
3.0 star property
Hawthorne
The price is ￥26,467
￥55,337 total
includes taxes & fees
Feb 4 - Feb 5
Bass Fishing Paradise w/ Shared Dock in Hawthorne!
Smart TV, fireplace

Raceway Retreat, just 12 miles from UF/downtown, relaxing country getaway!

Raceway Retreat, just 12 miles from UF/downtown, relaxing country getaway!
Gainesville
10.0 out of 10, Exceptional, (5 reviews)
"Property was just as listed. Just 1 one night stop over for us. Thought about going and watching some local racing, but rain prevailed. Anyone actually planning trip for a race weekend. This just might he your place"
United States
Allyson T.
The price is ￥13,930
￥36,954 total
includes taxes & fees
Feb 15 - Feb 16
Raceway Retreat, just 12 miles from UF/downtown, relaxing country getaway!
3 bedrooms, iron/ironing board, WiFi, bed sheets

The Canopy on 10th | Game Room • Pets • Pergola

The Canopy on 10th | Game Room • Pets • Pergola
Gainesville
10.0 out of 10, Exceptional, (10 reviews)
"Clean rooms, nice amenities, provided snacks and goodies. Would stay again!"
United States
Christian L.
The price is ￥13,621
￥43,676 total
includes taxes & fees
Feb 8 - Feb 9
The Canopy on 10th | Game Room • Pets • Pergola
Terrace/patio

Serene Place | Walk to UF • Free Parking • Kitchen

Serene Place | Walk to UF • Free Parking • Kitchen
Gainesville
10.0 out of 10, Exceptional, (5 reviews)
"Great place. "
United States
Mike M.
The price is ￥13,930
￥36,765 total
includes taxes & fees
Feb 8 - Feb 9
Serene Place | Walk to UF • Free Parking • Kitchen
Smart TV, offices

Fantastic Find in Finley Woods

Fantastic Find in Finley Woods
Gainesville
9.8 out of 10, Exceptional, (52 reviews)
"Great spot close to UF, quiet nice neighborhood. Spot is accurate to description and very nice. Great master tub!"
United States
Ed S.
The price is ￥10,832
￥38,538 total
includes taxes & fees
Feb 11 - Feb 12
Fantastic Find in Finley Woods
Exterior

Wilderness Getaway at The Grist Mill

Wilderness Getaway at The Grist Mill
Fort McCoy
The price is ￥21,453
￥37,507 total
includes taxes & fees
Feb 8 - Feb 9
Wilderness Getaway at The Grist Mill
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 Windsor Hotel Reviews

Super 8 by Wyndham Gainesville I-75 Hospital University Area

Super 8 by Wyndham Gainesville I-75 Hospital University Area

10/10 Excellent
"Staff always helpful and polite."
Cheryl 21-night trip
Posted 1 day ago
Super 8 by Wyndham Gainesville I-75 Hospital University Area

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
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Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, you can find vacation rentals close to popular sights in Windsor, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Windsor?

Family-Friendly Gainesville Home - Walk to UF - Pool + Sleeps 16: This vacation home rental outside of Windsor offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Florida Museum of Natural History, or get outside and enjoy nature at University of Florida Bat Houses. Gainesville Raceway and University of Florida are a couple of places you'll find in the larger area.

What are vacation rentals like in Windsor?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Windsor. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.