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Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Cottage in Hawthorne

4.85 out of 5 average rating, 110 reviews

Live Oak Oasis on Morris Lake

Unspoiled nature greets your every turn at this charming 650 SF lakefront retreat. A short distance from 10 of Florida's finest 1st magnitude springs, ranging from 30 - 90 minute drive, makes the location a perfect basecamp for adventure travel. Rest beneath the shade of Live oaks that pull the breeze ashore. Enjoy Sand hill cranes and hummingbirds from the cabana. Incredible sunsets from new dock. Paddle boat & paddle boards available for adventures. WiFi, Netflix, Laundry, HOT outdoor shower!

Sep 2 – 9

G$19,621 GYD per night

Guest suite in Gainesville

4.97 out of 5 average rating, 418 reviews

Private guest suite in a quiet modern farmhouse

This is an elegant and newly renovated private guest suite with its own separate entrance and private bathroom located in a 1950s single family residential home. Most of the furnishings are custom made! This is an ideal place to stay for visiting parents, traveling professional students, business travelers, general visitors to Gainesville, or anyone looking for a quiet place to stay. It is NOT a location to host parties, gatherings, or to hang out in groups. Please, NO SMOKING in our suite.

Sep 25 – Oct 2

G$13,505 GYD per night

Guesthouse in Gainesville

4.98 out of 5 average rating, 637 reviews

Unique Container "Caja Verde" 1 Mile UF & Downtown

Our home is less than a mile to UFHealth at Shands and the Malcom Randall Veterans Medical Center. We are a mile to the University of Florida campus. Amazingly, also a short bike ride (1-2 miles) to Downtown Gainesville. Close to Depot Park, art studios, restaurants, music venues, and theater. Nature parks close too. The bonus is we live on 2 acres, tucked back in a quiet neighborhood. Our pool is deep & cool; we have bikes to borrow. The container is perfect for a solo traveler, or a couple.

Jun 29 – Jul 6

G$18,354 GYD per night

Farm stay in Citra

4.99 out of 5 average rating, 153 reviews

Relaxing retreat located on working farm.

Charming cottage located on 5 acres of vineyard, and goat farm. Come experience peaceful country living. Stoll throughout the property, go pet the goats (very friendly South African boer goats)(with us in attendance). During season (end of July through September go pick your own pesticide free grapes (muscadine). Pick persimmons during their season September, October. Located near multiple natural springs. We are located half way between Gainesville and Ocala. The farm is located near WEC

Oct 22 – 29

G$22,100 GYD per night

Cabin in Branford

5.0 out of 5 average rating, 124 reviews

Sweetbay River Camp-Ichetucknee River Access

Come enjoy a peaceful getaway on four private acres *near* the Ichetucknee and the Santa Fe rivers! Float the crystal clear river, take your boat out, or just hang in the hammock and enjoy a bonfire! The cabin is in a wildlife sanctuary, so you will see many deer and other animals in the yard and around the neighborhood. The house comes with private access to an Ichetucknee tube/kayak launch as well as the exit point and a private boat ramp. Only four miles to Ichetucknee Springs State Park!

Oct 23 – 30

G$27,884 GYD per night

Cabin in Hawthorne

4.95 out of 5 average rating, 129 reviews

Charming Lakefront Log Home

Welcome to your perfect lake retreat! Located on a no public access lake. This charming log home has a private dock and boat ramp suitable for launching your boat for fishing or skiing. There are kayaks on premises for use. This is an ideal location to enjoy North Florida’s lake life with family, friends, or work retreat. Includes a fully stocked kitchen, covered porch, fire pit, gas grill, and WiFi if you feel the need to plug in. NOT suitable for parties or events. NO loud noise, please.

Jun 24 – Jul 1

G$35,662 GYD per night

Home in Micanopy

4.97 out of 5 average rating, 221 reviews

Beautiful House, Historic District, Micanopy

My Beautiful House is located in the heart of the historic district of Micanopy, Florida. Relaxing is a breeze in this wonderful home. Two large bedrooms and two equally spacious living areas are furnished with comfort in mind. There are two televisions with Directv service and free WiFi. The large backyard has lots of space and privacy! Established in 1821, Micanopy is the oldest inland town and the town that time forgot. Convenient to both Gainesville and Ocala via I-75 and SR 441.

Jan 7 – 14

G$31,304 GYD per night

Tiny home in Gainesville

4.92 out of 5 average rating, 105 reviews

Harmony Tiny House-NO Cleaning Fee

Beautifully built and decorated, Harmony Tiny house is located close to Newnan’s Lake but only a 10 minute drive to downtown. Surrounded by woods on 3 sides, it sits behind the main home on an acre of land with a small creek in the back. You have access to the back yard with an outdoor table and chairs and also a key to the utility room if you need to do a load of laundry. The sliding glass door entry faces the backyard. Please note that pets are allowed and there is a $30 pet fee.

Jul 11 – 18

G$16,488 GYD per night

Tiny home in Alachua

4.95 out of 5 average rating, 263 reviews

Ela's Tiny House: Springs, Trails & Disc Golf!

Ela's Tiny House is a 40ft Thomas School Bus converted into a unique and elegant experience! Nestled on 28 Acres of beautiful Florida nature, you can soak up the sun and unwind. Enjoy laying in a hammock and star gaze, catch a stunning sunrise or play a round of disc golf. Paddle board the Santa Fe River, swim with manatees @ Ichetucknee Springs, or soak in the cool waters @ Blue Springs. The Historic town of Alachua, High Springs and Gainesville all within a 20 min drive.

Jul 1 – 8

G$14,943 GYD per night

Cabin in High Springs

4.94 out of 5 average rating, 369 reviews

Getaway Gilchrist Springs - Orlando

An easy drive from the city, Getaway is a new way to experience the great outdoors. Nestled across dozens of acres of private woodlands, our modern, tiny cabins have everything you need (comfy bed, bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you relax, unwind and disconnect from the everyday. Plus, as part of your stay, you'll receive firewood, a s'mores kit, coffee and bottled water*.

Nov 17 – 24

G$24,770 GYD per night

Apartment in Waldo

4.99 out of 5 average rating, 148 reviews

Fernbank on beautiful Lake Alto. Laketime Getaway

Visit this beautiful, tranquil lakeside spot for an amazing getaway. It's a six acre property, an inspiring place to study, write, or get work done with fun things to do while on a break. Swim, kayak, canoe, paddle board or enjoy sitting on the dock. Visit the barn for basketball, ping pong, and corn hole. It's a studio apartment with a private bathroom and beds for four, plus two couches and air beds available. Note: This is an upstairs apartment.

May 7 – 14

G$22,283 GYD per night

Home in Micanopy

4.92 out of 5 average rating, 135 reviews

Quaint Guest Apartment

Conveniently located just south of Gainesville in Historic Micanopy, this fully furnished, temporary stay, private rental situated on 10 secluded acres would be ideal for parents visiting their children at UF, folks interested in catching a football game, couples driving down south for vacation and individuals here on business. This space is an extension of our home. It is cleaned and cared for by us and is not "just a business".

Jun 19 – 26

G$19,593 GYD per night

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Other great vacation rentals in Windsor

Farm stay in Williston

5.0 out of 5 average rating, 106 reviews

Happy House @beautiful Forever Spring Horse Farm

Jul 19 – 26

G$24,074 GYD per night

Guesthouse in Gainesville

4.98 out of 5 average rating, 158 reviews

Walk to UF! Historic King Bed Loft w/ Private Deck

Dec 15 – 22

G$23,444 GYD per night

Condo in Gainesville

4.99 out of 5 average rating, 334 reviews

Condo in the Heart of Haile Village-Great Location

Jul 18 – 25

G$24,967 GYD per night

Cabin in Alachua

5.0 out of 5 average rating, 102 reviews

Rose Cottage at Alpaca Acres

Feb 21 – 28

G$17,390 GYD per night

Home in Gainesville

4.81 out of 5 average rating, 113 reviews

El Ranchito

Dec 27 – Jan 3

G$21,134 GYD per night

Home in Earleton

4.97 out of 5 average rating, 177 reviews

Lake House Escape & Play

Jul 14 – 21

G$24,196 GYD per night

Apartment in Gainesville

5.0 out of 5 average rating, 218 reviews

Get-away condo in the heart of Haile Village.

May 27 – Jun 3

G$19,098 GYD per night

Apartment in Melrose

4.98 out of 5 average rating, 66 reviews

Lakefront Retreat Apartment Remodeled, Premium Bed

Aug 7 – 14

G$17,336 GYD per night

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