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Holiday rentals in Diamond Island

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Top-rated holiday rentals in Diamond Island

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

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Top guest favourite
An aerial view captures a serene swimming pool surrounded by a spacious patio. A separate guest house is visible near the pool, featuring a sloped roof and multiple windows. Lush landscaping offers privacy, while a clear pathway leads from the pool area to the nearby road.
Guest house in Evansville
4.87 out of 5 average rating, 253 reviews

Private Guest House close to everything!

The Private Guest House is set on our property which is located on a corner (1.5 acre lot) close to the east side of Evansville. The convenient large circle drive makes it easy to enter and exit. The east side of Evansville offers Malls, Shopping, Restaurants, Bars, Entertainment, Gyms, Starbucks, and Theaters. The property is located only 10 minutes from Downtown and the Ford Center due to close proximity to Lloyd Expressway. Check out the Casino and Riverfront if you’re in the Downtown Area!

Guest favourite
A comfortable living area is showcased with a spacious gray sofa adorned with blue and green cushions. A round wooden coffee table is centered on a large area rug. Two tall windows allow natural light to fill the space, complemented by a small dining table and chair.
Bungalow in Evansville
4.88 out of 5 average rating, 406 reviews

Fabulous on Historic First St. Near Haynies Corner

Light and airy with 11ft ceilings and warm wood floors, this 900 sq foot updated downtown 1 bedroom is just right for your next visit to Evansville. Whether you are in town for work or for play, this is a great spot for you. Located in the same block as Haynies Corner, two blocks from the river trail, and very close to Main Street, Ford Center and Old National events Plaza this home provides a great spot for the active life as well as the night life. Fully equipped, stainless appliances.

Top guest favourite
The exterior of a two-story building is showcased, featuring a red metal roof and a balcony with black chairs. A sign hangs above the entrance, while the river and sunset are visible in the background. A pathway runs alongside the building, with parked cars lining the street.
Loft in Newburgh
4.97 out of 5 average rating, 364 reviews

Riverfront Loft Above Honey Moon Coffee Shop

Located right on the riverfront in downtown Newburgh. Perfect access for walking, hiking, running, or bike riding on the popular riverfront trail. With epic views of the Ohio River including a 2nd story balcony view of beautiful sunrises and sunsets, our stylish loft apartment is located directly over Honey Moon Coffee shop. Please note that the loft is above a coffee shop that opens at 7am each day and you will hear some noise. 2 complimentary drip coffees are included with your stay!

Top guest favourite
Cabin in Dixon
4.96 out of 5 average rating, 322 reviews

Crouse’s North Ninety Lake House

If you want a place where you can be socially distanced, this is the place! (discounts for weekly or monthly stays.) The cabin is set in a 90 acre area surrounded by woods with two small lakes (fishing, walking trails and paddle boating available at no extra charge). There is only one other cabin on the 90 acres. Nearest town, Dixon (3 miles), Madisonville (20 miles, Henderson 21 miles), Evansville, IN (has a regional airport about 35 miles). Truly a relaxing getaway place.

Top guest favourite
The front of the cottage features a welcoming dark blue exterior with a bright red door, flanked by well-maintained gardens. Potted plants and colorful flowers enhance the entrance, providing a charming first impression. A small walkway leads to the door, completing the inviting atmosphere.
Cottage in New Harmony
4.98 out of 5 average rating, 425 reviews

New Harmony Cottage

Open concept cottage w lots of space for one or two located in the Historic District of New Harmony. Free street parking, a sitting area and comfortable queen bed. Washer/Dryer and a small kitchenette (no stove or cooktop.) WiFi and and a Smart TV for your convenience. Bring your Netflix or Hulu passwords. Be our guest in your own space. Easy no contact checkin & checkout. Coffee/Tea bar or Black Lodge Coffee! *FYI check hours for shops & restaurants that you plan on visiting.

Top guest favourite
The front exterior of the vibrant yellow cottage is framed by a white picket fence. A welcoming red door is centered beneath the front porch, which is supported by white columns. Lush green grass lays in the yard, with two hanging planters on either side of the door.
Cottage in New Harmony
4.99 out of 5 average rating, 108 reviews

Honeycomb Hideaway

Welcome to Honeycomb Hideaway, a vibrant yellow cottage nestled in the heart of historic New Harmony, Indiana. Our cozy one-bedroom retreat offers a peaceful and exciting escape, just steps away from Murphy Park, fantastic restaurants, and captivating tourist activities. Immerse yourself in New Harmony's rich heritage, exploring charming streets, unique shops, and art galleries. Indulge in local cuisine or embark on outdoor adventures in parks and walking trails.

Top guest favourite
An open-concept living area is highlighted by exposed brick walls and wooden flooring. A comfortable seating arrangement includes a sofa and two chairs, inviting relaxation. The kitchen features modern appliances and a breakfast bar with stools, with natural light streaming through large windows.
Home in Evansville
4.93 out of 5 average rating, 106 reviews

Downtown Haven Retreat

Welcome to the Dr. J.R. Mitchell House! Built in 1909 as what is believed to be the first animal clinic in Evansville, this century-old home has been renovated and modernized. This downstairs apartment was Dr. Mitchell’s original animal clinic while his family’s quarters was located upstairs. Inside, you’ll discover urban comfort at our 2 bed, 2 bath apartment and be just steps away from shopping, dining, and all that the downtown riverfront area has to offer.

Top guest favourite
A historic brick building stands on a cobblestone street, framed by mature trees and shrubs. The entrance features a set of stairs leading to double doors adorned with decorative glass. A lamppost adds charm to the inviting outdoor space.
Flat in Evansville
4.95 out of 5 average rating, 240 reviews

Victorian 1 Bedroom Guesthouse Apt on 1st Street

This one-bedroom / one-bathroom apartment features high ceilings and exposed brick and is attached to your host’s home - a Victorian townhouse on one of Evansville’s historic cobblestone streets. Enjoy easy self-check-in and a location that is centrally located near the Ohio River, Downtown Evansville, and Haynie’s Corner neighborhoods. The Ford Center, Bally’s Casino, and many of Evansville’s best restaurants and bars are all a short walk away.

Guest favourite
A single-story home with a light blue exterior sits in a quiet neighborhood. The well-maintained front yard features small shrubs and landscaping, while a paved driveway provides easy access. Trees in the background showcase autumn colors, enhancing the peaceful environment.
Home in Evansville
4.87 out of 5 average rating, 102 reviews

Kozy Kathleen

*Currently listed as top 10 AirBnbs in Evansville, IN. *Kozy family home in a quite neighborhood with 2 car capacity drive way including street parking if necessary. *Full of amenities needed for any length of stay. Close to I-69 and HWY 41 for any travel requirements. *Less than 5 miles from the heart beat of Evansville (Ford center/ downtown/ and Eastland mall). *"The Kozy Kathleen" = Real Hoosier home with authentic mid-west feel.

Guest favourite
A white single-story house is framed by lush green landscaping. Two windows with gray shutters are visible on either side of the front door, which is painted in teal. A pathway leads to the entrance, surrounded by tall grass and leafy plants.
Flat in Evansville
4.79 out of 5 average rating, 352 reviews

Best Value/Sleeps 4/ Cozy/Center Town /Pets ok!

This is a private unit, but There is a GUEST SUITE attached to this listing (also available on Air BNB.) However, there are NO shared spaces. Each listing has a separate entrance. Near shopping, restaurants. 1Bedroom-2 queen beds-1bath cable/wifi, stocked wi/ snacks & amenities. Key lock box entry, Washer/Dryer. Couch folds down with a pull out feature on the base see pics or contact us to operate.

Superhost
Guest house in Henderson
4.87 out of 5 average rating, 94 reviews

Downtown 1 bed & 1 bath studio guest house

Enjoy easy walkable access to downtown Henderson festivals, restaurants, and river fun when you stay in our guest house. This one-bedroom 1 bathroom studio space has a private entrance, free parking, and access to an outdoor deck with seating Enjoy ammenities such as a queen-size mattress, 50" smart tv, full-size refrigerator, blow dryer, Keurig, and more.

Top guest favourite
A comfortable living area is furnished with a gray sofa adorned with decorative cushions. A round coffee table is placed at the center, while a TV is mounted on the wall. A red chair adds a pop of color, complemented by soft lighting and tasteful wall decor.
Home in Mount Vernon
5 out of 5 average rating, 57 reviews

The Brick Abode

The Brick Abode is a clean, comfortable, locally-owned, short-term rental catering primarily to contract workers and visiting families. The home is a 2 bed, 1 bath with a covered back porch perfect for relaxing and enjoying the evening. You'll find a completely furnished home ready for an individual or family in a quiet neighborhood.

Popular amenities for Diamond Island holiday rentals