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Holiday houses 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.
Guesthouse in Evansville
4.85 out of 5 average rating, 220 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!

Top Guest favourite
Home in Mount Vernon
5 out of 5 average rating, 12 reviews

The Cypress Cottage

Pickleball anyone? Looking for a quiet place to disconnect and unwind? You’ll love this 1878 cottage getaway. With 4 bedrooms, there is plenty of room for you to kickback and relax. Cook a meal in the full kitchen and step outside and play pickleball on the private, woods surrounded court. Washer and dryer are included at this country getaway. A short drive to historic New Harmony and Evansville so you can attend events like Kunstfest and the Fall Festival. Also not far from USI & U of E.

Top Guest favourite
A wooden door with multiple panes opens into a cozy sitting area. Outdoor seating is provided by a small table and two chairs on a gravel patio. Natural light filters through the door, highlighting the inviting interior and lush greenery outside.
Guesthouse in Evansville
4.9 out of 5 average rating, 653 reviews

Nest: 1905 Carriage House Apartment

Our renovated 1912 carriage house was designed exclusively for Airbnb guests! Set in the midst of Semper Fulgens gardens, this luxury apartment is small but features a large bathroom with clawfoot tub, a loft bedroom with king sized bed, a sitting area, and coffee bar. There is not a full kitchen, but we do have a fridge. Not suitable for kids. A place for pet lovers! We do have two dogs, a cat and chickens who live on the property and have access to courtyard and event space.

Guest favourite
A serene lakeside view captures a quaint cabin reflected in calm waters. Lush green grass surrounds the water's edge, while trees frame the background under a blue sky dotted with clouds.
Cabin in Dixon
4.96 out of 5 average rating, 309 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
4.99 out of 5 average rating, 413 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, 102 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.

Guest favourite
The entrance to the cabin is framed by wooden siding, featuring a central door adorned with a seasonal wreath. Natural elements, including pumpkins, are arranged on a small porch flanked by rustic decorations and a wooden fence made of branches.
Cabin in Dixon
4.91 out of 5 average rating, 519 reviews

Handcrafted Cabin in Woodsy Heaven

PLEASE read listing before booking. Custom built wood cabin nestled in the rolling hills of western Kentucky. Cozy decor with vintage theme, handcrafted wood floors, and outdoor space overlooking wooded property. Rustic studio space full of modern amenities. Close proximity to 5450 acre Wildlife Management Area with hiking, horseback riding, fishing, hunting, and swimming. Perfect location to get back to nature. Great peaceful weekend or overnight getaway.

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.
Apartment in Evansville
4.95 out of 5 average rating, 222 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.

Top Guest favourite
An open living area showcases original exposed brick walls and modern amenities. A spacious kitchen island is paired with stainless steel appliances. The living space features a sectional couch facing a large projector screen, with ambient lighting provided by pendant fixtures.
Home in Evansville
4.96 out of 5 average rating, 224 reviews

Rooftop Views in the Heart of Downtown!

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. Dr. Mitchell's owners' quarters above the original animal clinic now features two bedrooms, an open bunk room for kids, and three full bathrooms. You'll find the original exposed brick throughout the home which adds the perfect vibe to this modern industrial home.

Guest favourite
Guest suite in Evansville
4.82 out of 5 average rating, 257 reviews

Private Suite/Sleeps 3/Center Town/Pets OK!

Guests will have their own entrance and is closed off from the rest of the house. It is a 2 room space (250sf) Has a queen memory foam bed . A bathroom and a kitchenette in the next room (with microwave, coffee maker, mini fridge, panini press) fold down couch for 3rd guest You will get much more from us than a hotel room and much cheaper! Pet fees $20 per stay $5 guest fee per day after 2.

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
4.98 out of 5 average rating, 332 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. 2 complimentary drip coffees are included with your stay.

Guest favourite
An indoor pool area features a long, narrow pool, surrounded by large windows that allow natural light to fill the space. The tiled floor is complemented by potted plants, and wicker chairs with cushions are arranged nearby for seating.
Holiday home in Evansville
4.94 out of 5 average rating, 189 reviews

Nugent House

It's rare to find a place that's both historic and one-of-a-kind. Whole house to enjoy in downtown Evansville Indiana. Walking distance to arts district , bars , restaurants, casino , ford center , Evansville museum, Evansville riverfront and much more.,, Home was built in 1915 as a mansion by the Nugent family. No lifeguard on duty, swim at your own risk

Popular amenities for Diamond Island holiday rentals