Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Windsor vacation rentals

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
$315 nightly
The price is $351
Apr 14 - Apr 15
Total with taxes and fees
Hawthorne Angler's Cabin w/ Lake + Dock Access!
View from property

Yearling Restaurant and Cabins

Yearling Restaurant and Cabins
2.5 star property
Hawthorne
9.2 out of 10, Wonderful, (207 reviews)
"The Yearling Cabins are somewhat remote. I planned my stay around a guided tour at the Marjorie Kinnan Rawlings State park and dining at the Yearling Restaurant."
United States
Sarah
$139 nightly
The price is $156
Apr 13 - Apr 14
Total with taxes and fees
Yearling Restaurant and Cabins
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, (2 reviews)
"Was a great place to unwind after a long day at work. Very relaxing, very quiet"
United States
Matthew g.
$89 nightly
The price is $96
Apr 13 - Apr 14
Total with taxes and fees
Charming 1-bedroom house with AC, WiFi in welcoming Melrose
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, (15 reviews)
"Awesome location, great cabin! Had everything I needed to see my family ❤️ Will request to stay again!"
United States
Bonnie
$178 nightly
The price is $198
Apr 17 - Apr 18
Total with taxes and fees
White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing
Terrace/patio

Fish from own dock or in Palatka, Visit Ocala National Forest, FU Gators 30+ min

Fish from own dock or in Palatka, Visit Ocala National Forest, FU Gators 30+ min
Hawthorne
10.0 out of 10, Exceptional, (20 reviews)
"Great place to stay. Quiet, clean, with great recreational fishing off dock in back of the yard, along with other fishing areas close by."
United States
Tommye R.
$279 nightly
The price is $307
Apr 13 - Apr 14
Total with taxes and fees
Fish from own dock or in Palatka, Visit Ocala National Forest, FU Gators 30+ min
Interior

Orange Blossom in Historic McIntosh

Orange Blossom in Historic McIntosh
McIntosh
10.0 out of 10, Exceptional, (107 reviews)
"Relaxing, simple elegance!Quiet, and relaxing, comfortable beds, and seating around the home .The porch is the perfect place to enjoy a book or out a puzzle together.Looking forward to staying again."
United States
Jane S.
$204 nightly
The price is $225
Apr 15 - Apr 16
Total with taxes and fees
Orange Blossom in Historic McIntosh
TV

Bass Fishing Paradise w/ Shared Dock in Hawthorne!

Bass Fishing Paradise w/ Shared Dock in Hawthorne!
Hawthorne
10.0 out of 10, Exceptional, (1 review)
"Thank you for letting us stay. We had a great time fishing."
United States
cheryl M.
$313 nightly
The price is $345
Apr 13 - Apr 14
Total with taxes and fees
Bass Fishing Paradise w/ Shared Dock in Hawthorne!
Terrace/patio

Palmetto Cottage-1930’s Florida Cottage

Palmetto Cottage-1930’s Florida Cottage
Micanopy
9.8 out of 10, Exceptional, (55 reviews)
"House was interesting and comfortable, location was perfect and I fell in love with Micanopy.."
United States
Robin
$204 nightly
The price is $225
Apr 15 - Apr 16
Total with taxes and fees
Palmetto Cottage-1930’s Florida Cottage
Exterior

Juniper Cottage — In the Heart of Old Florida

Juniper Cottage — In the Heart of Old Florida
Micanopy
9.4 out of 10, Exceptional, (17 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.
$207 nightly
The price is $228
Apr 13 - Apr 14
Total with taxes and fees
Juniper Cottage — In the Heart of Old Florida
Interior

Azalea Farmhouse

Azalea Farmhouse
McIntosh
9.8 out of 10, Exceptional, (51 reviews)
"I enjoy staying here very much! It’s a perfect place for quiet serenity!"
United States
Susan P.
$207 nightly
The price is $228
Apr 13 - Apr 14
Total with taxes and fees
Azalea Farmhouse
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
$309 nightly
The price is $344
Apr 13 - Apr 14
Total with taxes and fees
Bass Fishing Paradise w/ Shared Dock in Hawthorne!
Interior

Relaxing Lakefront Cottage

Relaxing Lakefront Cottage
Fort McCoy
10.0 out of 10, Exceptional, (17 reviews)
"We thoroughly enjoyed our stay!"
United States
Jennifer C.
$236 nightly
The price is $261
Apr 13 - Apr 14
Total with taxes and fees
Relaxing Lakefront Cottage
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, (11 reviews)
"Great property and awesome host. "
United States
Claude L.
$277 nightly
The price is $297
Apr 13 - Apr 14
Total with taxes and fees
The Canopy on 10th | Game Room • Pets • Pergola
Smart TV, offices

Fantastic Find in Finley Woods

Fantastic Find in Finley Woods
Gainesville
9.8 out of 10, Exceptional, (53 reviews)
"Great spot close to UF, quiet nice neighborhood. Spot is accurate to description and very nice. Great master tub!"
United States
Ed S.
$220 nightly
The price is $245
Apr 13 - Apr 14
Total with taxes and fees
Fantastic Find in Finley Woods
Interior

Charming 2-bedroom Cottage in Gainesville. 10 to UF

Charming 2-bedroom Cottage in Gainesville. 10 to UF
Gainesville
9.8 out of 10, Exceptional, (6 reviews)
"Cozy place just a short drive to the Swamp!"
United States
Willie B.
$200 nightly
The price is $223
Apr 13 - Apr 14
Total with taxes and fees
Charming 2-bedroom Cottage in Gainesville. 10 to UF
Fridge, microwave, oven, stovetop

Beautiful 3 Bedroom Home in Quiet Neighborhood

Beautiful 3 Bedroom Home in Quiet Neighborhood
Gainesville
9.6 out of 10, Exceptional, (19 reviews)
"The host was very welcoming and responsive. The house was clean, cozy and the beds were extremely comfortable. "
United States
Donna H.
$285 nightly
The price is $318
Apr 13 - Apr 14
Total with taxes and fees
Beautiful 3 Bedroom Home in Quiet Neighborhood
Terrace/patio

Great place to meet up

Great place to meet up
Gainesville
9.8 out of 10, Exceptional, (7 reviews)
"We were very impressed by the property. Very clean, loved the decor, furniture, the layout. The property was very elegant and inviting. Will recommend this property to everyone."
United States
anissa m.
$345 nightly
The price is $383
Apr 13 - Apr 14
Total with taxes and fees
Great place to meet up
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.
$139 nightly
The price is $154
Apr 20 - Apr 21
Total with taxes and fees
"La Grande" Retro Escape
Terrace/patio

Gainesville Hideaway

Gainesville Hideaway
Haile Plantation
9.6 out of 10, Exceptional, (16 reviews)
"Great location and a great place to stay, especially if the market is in town. "
United States
chad s.
$242 nightly
The price is $270
Apr 15 - Apr 16
Total with taxes and fees
Gainesville Hideaway
Fridge, microwave, oven, stovetop

Luxurious Home in Upscale Neighborhood. EV Charger. Furnished backyard patio.

Luxurious Home in Upscale Neighborhood. EV Charger. Furnished backyard patio.
Gainesville
10.0 out of 10, Exceptional, (37 reviews)
"Beautiful house, comfortable stay and the host is super responsive. Would definitely recommend staying here when in Gainesville!"
United States
Lori C.
Luxurious Home in Upscale Neighborhood. EV Charger. Furnished backyard patio.
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

HOM Hotel Gainesville, SureStay Collection by Best Western

HOM Hotel Gainesville, SureStay Collection by Best Western

10/10 Excellent
"Breakfast menu was fresh and parking felt safe and easy!"
Paola 2-night trip
Posted 3 hours ago
HOM Hotel Gainesville, SureStay Collection by Best Western

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $124 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 Santa Fe Lake. Thomas Center and Gainesville Raceway 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.