Vacation rentals in Diamond Island

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Top-rated vacation rentals in Diamond Island

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

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Top guest favorite

Home in Evansville

Historic Haynie's Corner Hideout

Warm, cozy and spacious historic home located right near the vibrant Haynie's Corner. Features original art from local artists as well as others. Inviting living spaces, fully stocked kitchen and coffee bar, large dining room and cushy bedrooms all make for a great place to relax, unwind and enjoy your stay away from home. Work area, gaming nook, comfortable sun porch, side yard fire pit and lounge area take your stay to the next level! We look forward to creating a wonderful experience for you.

LocationFamilyAir conditioning

4.95 out of 5 average rating, 110 reviews

Guest favorite

A spacious living room features a large sectional sofa arranged around a textured area rug. A coffee table is positioned at the center, complemented by a decorative plant. Natural light brightens the room from the windows, with a ceiling fan providing comfort.

Home in Evansville

Chestnut Haven

Welcome to this beautifully updated 3-bedroom, 2-bathroom home, perfectly designed for comfort and convenience. Located in an idyllic neighborhood, this home boasts a thoughtful layout and contemporary finishes that make it truly stand out. This home is only 8 minutes from the Ford center and 5 minutes from restaurants and shopping. There is a dedicated office if you're traveling for work, and dogs are most welcome to stay! There is a back deck with patio furniture and a garage for you to enjoy!

ValueLocationHospitality

4.87 out of 5 average rating, 115 reviews

Top guest favorite

A charming single-story home features a welcoming yellow front door framed by a wreath. Flanking the door are two black chairs on a subtly illuminated front porch. Lush greenery and decorative plants surround the entrance, complemented by a stone pathway leading to a well-kept lawn.

Home in Mount Vernon

Convenient, Comfy and Cozy

Centrally located near Mt Vernon High School.Sleeps five. Space to spread out and be active both indoors and out. Pets welcome. Enjoy the fenced yard. The two bedrooms have room darkening shades for sleeping in. A love seat with a single pullout bed in sunroom along with a piano, a ukulele, 1/2 size guitar, and a turntable with vintage LP’s. Fully equipped kitchen. Finished basement with additional tv area, ping pong, Pac-Man arcade, games and more. Also has a washer/dryer and a second bathroom.

LocationFamilyDecor

5.0 out of 5 average rating, 17 reviews

Top guest favorite

Home in Mount Vernon

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.

FamilyLocationKitchen

5.0 out of 5 average rating, 23 reviews

Guest favorite

A contemporary living area features two patterned armchairs beside a small round table with a decorative lamp. Abstract artwork adorns the brick wall, while a textured rug adds comfort underfoot. Soft, ambient light enhances the inviting space.

Loft in Evansville

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!

LocationFamilyCondition

4.98 out of 5 average rating, 127 reviews

Top guest favorite

Cabin in Dixon

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.

ValueLocationLong stay

4.96 out of 5 average rating, 352 reviews

Guest favorite

The interior showcases a warm, wooden design with vaulted ceilings and exposed beams. A modern television is mounted on the wall above a stone fireplace, while a cozy seating area is arranged with a dark sofa and wooden coffee table. The space is well-lit and inviting.

Cabin in Corydon

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.

ValueLocationPets

4.93 out of 5 average rating, 143 reviews

Top guest favorite

Home in Evansville

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.

LocationFamilyAccess

4.96 out of 5 average rating, 283 reviews

Top guest favorite

An open living area features large windows that allow natural light to fill the space. A comfortable sofa and patterned chair are arranged around a central area rug. A wooden table and chairs are positioned nearby, offering additional seating options.

Loft in Henderson

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!

LocationValueIndoor spaces

4.99 out of 5 average rating, 111 reviews

Top guest favorite

Home in Corydon

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.

ValueLocationKitchen

4.96 out of 5 average rating, 241 reviews

Superhost

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.

Vacation home in Evansville

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

LocationValueBreakfast

4.93 out of 5 average rating, 220 reviews

Top guest favorite

Guesthouse in Henderson

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.

ValueFamilyKitchen

4.9 out of 5 average rating, 123 reviews