Holiday rentals in Diamond Island

Large 5BR + Game Room + Firepit, Prime Location

Welcome to Heights Haven Retreat, your home away from home! This spacious 5-bedroom, 3-bath home spans 3,500 sq ft across three levels. It's perfect for families and groups. Enjoy a huge dining table for 12, a game room with pool table and arcade games, and a fenced backyard for relaxing evenings. Located minutes from top restaurants, shopping, and attractions, this home combines comfort, fun, and unbeatable convenience. Whether you’re here to explore or unwind, this is your home away from home.

The Mint Julep! Upstairs 3BD/2BA - Next to Brewery

Book your stay at The Mint Julep and experience Henderson like a local. Fresh vibes, classic charm, and a stay worth toasting. You are "mint" to make memories at The Mint Julep. Welcome to The Mint Julep, a stylish and spacious upstairs retreat in the heart of Henderson, Kentucky! This 3-bedroom, 2-bath rental is perfectly located adjacent to Henderson Brewing Co., near Holy Name Church, and just a short walk from downtown restaurants, shops, riverfront attractions, and seasonal festivals.

The Nest - Huge Loft in Downtown Henderson

Welcome to The Nest, Henderson's finest loft! This Victorian 1800 sq. ft. loft is newly renovated, fully furnished and nicely appointed in the heart of Downtown Henderson. The huge living room is perfect to meet friends, watch TV, cook, or just gaze out the massive windows. The Master Room, Reading Room (featuring a queen Murphy bed), fully equipped Kitchen, and Private Patio are quiet spaces to relax, work, prepare a meal, or plan your day. Parking, fast wifi, and washer/dryer all included!

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!

Spa feel sleep 6 wk/mo discounts

Beautifully renovated & stylishly decorated, this charming 3-bedroom, 2-bath brick ranch offers modern comfort in a prime west side location. Just minutes from USI, you’ll also enjoy easy access to shopping, a variety of restaurants, and a nearby movie theater. Relax in the inviting living room for a movie night or bask in natural light in the cozy sunroom with your favorite book. This home perfectly blends style, convenience, and warmth—ideal for both relaxation and entertainment.

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.

The Geneva Cabin

The Geneva Cabin is one of a kind (not in the woods) and has everything you need to enjoy whatever occasion brings you to the area. Located less than 2 miles from the wildlife refuge, 10 min to downtown Henderson, 7 mi to I-69 the property sits in the middle of a quiet dead-end street. Right in the middle of anywhere anyway your journey takes you. 55” TV, sofa bed and recliner in living room, WIFI, washer & dryer. Fully equipped kitchen. Large parking area.

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.

Rooftop Deck + 100" Theater | Downtown Evansville

Step into history at the Dr. J.R. Mitchell House (1909) — Evansville's first animal clinic, now a modern industrial retreat in the heart of downtown. Exposed brick, a private rooftop deck with city views, a 100-inch projector theater with surround sound, and a jetted tub for two. Walk to the riverfront, Ford Center, and Main Street dining. Fast WiFi and a dedicated workspace make it an easy home base for business and medical travelers.

The South by Davis Properties MTV

The South by Davis Properties MTV is a spacious and inviting studio apartment located in Mount Vernon, IN. With nearly 600 sq ft of living space, this studio feels bright, comfortable, and much larger than a traditional hotel space. The open floor plan provides plenty of room to spread out, making it an excellent choice for traveling professionals, contractors, healthcare workers, couples, and extended stay guests.

The Farm

Step away from the fast pace of daily life and enjoy family, friends and the peace of country living. Secluded modern farm house, that began as a log cabin, situated on approximately 100 acres of crop fields and includes a scenic lake. This property has been in our family for over 100 years. It has been lovingly furnished and decorated for a one of a kind stay. We want our guests to unplug, refresh, and renew.