Vacation rentals in Jacksonville

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Jacksonville

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Cabin in Winchester

4.96 out of 5 average rating, 163 reviews

Container Home GREAT Countryside Views COZY Stay

Singing Hills Cabin is the ultimate getaway for fresh air and an unbeatable view of the countryside. Enjoy morning coffee as the sun rises from the large front porch. This newly renovated container home is perfect for small families looking for an outdoor escape or for couples seeking a romantic getaway. It is located on a 40 acre hobby farm, so do not be surprised if you see cows and other wildlife during your stay! The best deer hunting, river access, and restaurants are located minutes away.

Guest favorite

Home in Pittsfield

4.85 out of 5 average rating, 239 reviews

Florence Guest House

ONE DAY ADVANCE NOTICE BOOKING! This 1,200 sq. ft. PRIVATE BOOK is a 175 year old building that Abe Lincoln stayed in. Central A/C, Forced air heat, Two decks (one overlooking the Illinois River), burn pit, outside grill, fully equipped kitchen, screened in porch, ample parking, access to the Illinois River/ boat ramp near, tie up on Our Private Lots! NOTE: RECENTLY HAD Guests' wanting to "JUST GET AWAY" for A Time!!! PRIVATE TIME ALONE, Guaranteed!!! NEW KEURIG; BRING YOUR K-CUPS!!!***

Guest favorite

Home in Havana

4.95 out of 5 average rating, 128 reviews

Private Beach • Lakefront • Kayaks • Sunsets

The Havana Cabana is your home away from home. Take time to breathe and just be by soaking in your surroundings and being with the people that matter most. We strive to provide you with a relaxing atmosphere and great amenities. You will have full access to your own private, sandy beach (directly behind the home) with amazing sunset views and great fishing. We provide 3 adult kayaks, one double and one child (under 150 pounds), and a pedal boat. Great outdoor fire-pit for s’mores and memories.

Top guest favorite

Tiny home in Springfield

4.98 out of 5 average rating, 464 reviews

Tiny Home Cabin - No Cleaning Fee

You won’t forget the peaceful surroundings of this rustic destination. It maybe small at 375 sf, but it has all the features of most hotels with one queen bed and a full bed in the loft. Located near downtown Springfield, IL and many Abraham Lincoln attractions. Deer often walk around the property which is on a quiet dead-end street. The kitchen has most everything you need to cook meals. Plenty of towels, soap, shampoo, and extra pillows too. Also watch Netflix, Hulu, Prime, and Disney.

Guest favorite

Home in Winchester

4.91 out of 5 average rating, 141 reviews

Winchester Guest Cottage

The Winchester Guest Cottage is a chance to experience the past while still enjoying the comforts of modern living. Guest will appreciate the living history of this mid 1800s home with much of its original architecture still intact. Enjoy the natural light from the tall windows while peering out through much of the original wavy glass. Most of the homes original wood work, doors and fireplace mantel are still there as they were in the 1800s. The floors were repurposed from WHS in the 1950s.

Top guest favorite

Loft in Virginia

4.94 out of 5 average rating, 166 reviews

Two Doors Down Loft, Virginia-Lincoln territory!

Located in VIRGINIA, IL-Our fantastic, urban vibed loft sits on the town square across from the town's historical courthouse. We are 30 minutes from Springfield, 15 minutes from Jacksonville and in the middle of Abe Lincoln territory and historical markers. The loft is also surrounded by lovely wineries and wildlife parks. Be sure to thoroughly read our listing to ensure that we'll meet all of your needs in exploring our unique area. Two Doors Down is a hidden gem listed at a super price!

Top guest favorite

Townhouse in Murrayville

4.98 out of 5 average rating, 307 reviews

Peace on the Prairie Too - Tiny House

Need a break from Politics? Peace on the Prairie accepts all guests for who they are rather than what some might wish them to be. Whether it’s a business trip, romantic time together with your significant other, a family vacation, a girl's time away, a secluded spot to work on your music, writing, art, star gazing, or a reconnection with nature, you'll find your inspiration and renewal in this natural rural setting of 23 acres of restored prairie, timber, and wetlands?

Top guest favorite

Cabin in Jacksonville

4.97 out of 5 average rating, 344 reviews

Bunkhouse Seventy-Four

Once used by seasonal farm labor in the 1930s, Bunkhouse Seventy-Four is a fully restored historic bunkhouse with all the modern amenities for a comfortable getaway. Perfect for couples, it features a full kitchen, bath, queen bed, a spacious porch, beautiful antique stained glass windows, a private outdoor soaking tub (Apr-Nov) on a 7 acre hobby farm. Also check out our listing, Audrey’s Abode, which is next door. Pets are welcome but we charge a $25 pet cleaning fee.

Top guest favorite

Home in Beardstown

4.98 out of 5 average rating, 252 reviews

My Little Bungalow on Monroe Street.

My Little Bungalow on Monroe is a family friendly, stylish bungalow that is a welcoming space in a peaceful Beardstown neighborhood. Only two blocks from the city square, the Bungalow on Monroe is within easy walking distance of several local eateries, and festival events held in the city square. This two bedroom home is has one queen bed, three twin beds and a daybed. A washer and dryer, as well as a second shower are available in the basement.

Guest favorite

Loft in Winchester

4.96 out of 5 average rating, 124 reviews

The Bike Flat

Visit historic Winchester and explore what our quaint community has to offer! This stylish place to stay is perfect for a quiet getaway and can accommodate groups thanks to its ample space. You can bring the family or plan a getaway with friends. The flat is located above a newly opened bicycle and coffee shop that also offers craft beers and wine. We hope you will consider choosing our rural accommodations for a trendy and relaxing experience!

Top guest favorite

Place to stay in Virginia

4.99 out of 5 average rating, 329 reviews

Virginia Lake Getaway/Fishing/Hot Tub/Hammock

Welcome to your charming log cabin located in Virginia, IL. This 1-bedroom, 1-bathroom cabin is designed to provide you with rustic comfort, making your stay truly exceptional. Nestled on a bluff overlooking the serene Virginia Lake, this 1850's log cabin combines historic charm with modern luxuries. Set on 80acres of timber and water for you to explore. Hike, kayak, fish or just relax and enjoy!

Top guest favorite

Home in Beardstown

5 out of 5 average rating, 312 reviews

The Little White House by the River

Beardstown's original Airbnb location, our home is called the Little White House by the River, and offers a quiet place to stay that is literally a stone's throw (if you've got a decent arm) from the back waters of the Illinois and Sangamon Rivers. DUE TO MAJOR PLANNED RENOVATIONS, THIS LOCATION WILL NOT BE AVAILABLE AFTER SEPTEMBER 30. 2025.