
Holiday houses in Diamond Island
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Top-rated holiday rentals in Diamond Island
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House Near U of Evansville and Ford Center
Stay at this peaceful and centrally located home with fenced yard. The house has been completely remodeled and is located 5 blocks from the University of Evansville and 7 minutes from downtown Evansville for concerts, shows and conventions. The house is located in a quiet safe neighborhood and is 15 minutes from anywhere in town. The house has 2 bedrooms, each with a queen bed, sleeping 4 total. One queen bed has an adjustable base to adjust head and legs in various positions for maximum comfort

Hobbit House 2 bedroom.
Welcome to the Hobbit House! Relax or work from home in this cozy house located in a charming, quiet neighborhood in central Evansville. Each room is curated to set a different vibe from relaxation, sophistication, and fun. This house also has an old speakeasy downstairs filled with arcade games and a movie projector and screen. At night relax in the backyard under a beautifully lit gazebo. This house is also equipped with an office set up to make it easy to work from your home away from home.

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.

The Cooper I on Franklin (The Ashby Collection)
Right in the heart of Franklin Street! All the “city feels” in this contemporary walk up loft! We provide all the pleasures, perks and pampering of a hotel, but in a fully-furnished private luxury residence. Just steps away from incredible restaurants, bars, pubs, live music, and specialty boutiques. Once you’ve arrived at The Cooper, grab a seat at our window bar overlooking Historic Franklin Street! We have equipped you with everything from a well appointed kitchen to a fabulous hot tub!

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!

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.

Haven on the Hilltop, Built in 1864
This home, built in 1864, promises an unforgettable stay, where timeless charm meets modern luxury. A short drive to USI, Mesker Zoo, Disc Golf Course, Helfrich Golf course, and Franklin St. which hosts the Fall Festival, boutiques & bars. Upon entering, guests are met with hardwood floors and a driftwood dining table. Guests have full access to this 3 BR and 1 bath and parking for 5 standard vehicles (see photo for parking visual). We hope you will find a haven in your stay!

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.

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.

The Lifeboat Loft - in the Heart of Henderson
Welcome to The Lifeboat Loft, our luxury apartment in Downtown Henderson KY! This unique 1100 sq ft loft on Main Street features soaring ceilings, a comfy king bed, upscale furnishings, a fully equipped kitchen, washer/dryer, high speed WiFi and a cool rolltop desk work area. 7 restaurants and the Vault venue are within 1 block. The new couch features a hideaway bed for extra company. It’s even friendly to your furry friends!

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.

Cozy Cottage | Free Parking | West Evansville
Charming 2BR/1BA cottage on Evansville's west side. Fully equipped kitchen with granite countertops and stylish blue backsplash. Fenced backyard with doggy door for pets. Free driveway parking, in-unit laundry, fast WiFi, and a dedicated workspace. Quiet residential neighborhood near Burdette Park, restaurants, and shops. Weekly and monthly discounts available for extended stays.
Popular amenities for Diamond Island holiday rentals
Other great holiday rentals in Diamond Island

Quiet 2 bd, 1 bath house with Smart TV.

Clean, Modern Space Near Hospitals & Campus

Leaning House of Haynie A | 2BD/1BA Trendy Apt

Main Street apartment, one block from river

City’s Edge II 2 Br/2 Ba K Q Laundry WIFI

Convenient, Comfy and Cozy

Lakeside Log Cabin: Venue • Hunting • Fishing

Private Retreat - 9 miles from Garden of The Gods
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