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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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Condo in St. Joseph

4.86 out of 5 average rating, 7 reviews

Surf Loft – Vacay Dwntn nr Beach, Park, Amenities

Surf Loft in St. Joseph, MI - the best of all vacation worlds. A gorgeous living space. Fireplace, flat-screen TVs, pro Foosball. Huge posh deck with gas grill. Walk to the beach, park, harbor, arboretum or thru downtown's boutiques, shops, eateries, art museum and more! Featuring spacious open design LR-DR-Kitchen, fabulous natural light, elegant-comfy bedrooms and deluxe bathrooms. Your and your guests' R-and-R levels will be off the charts. Morning coffee of the finest kind, anyone? Oh, yeah.

Cottage in Lakeside

4.79 out of 5 average rating, 48 reviews

Fun Duplex 200Yds 2 Lake Michigan-Pool/HotTub&More

Two 4 Bedroom 2 Bath Cottages only steps to private Lake Michigan Beach. Dedicated rental Cabins each w/ Chef's Kitchen, Updated Design w/ modern amenities. Kids & adults enjoy the amazing Pool and Hot Tub (Seasonal availability). Near Lakefront, Fruit Picking Farms, Vineyards, Warren Dunes St. Park, Golfing, XC Skiing, Union Pier & Three Oaks where kids play at Timbertown. 5 min. to New Buffalo to charter fishing boats & witness amazing views of harbor & sunsets from restaurant roof-top deck.

Cottage in Union Pier

4.98 out of 5 average rating, 211 reviews

"The Pines" in Union Pier: Year-round getaway

Under towering pine trees that feel more like the Northwoods, you're in the heart of Harbor Country. About 1.25 miles from the shore, minutes from New Buffalo & Three Oaks. Newly updated cabin-style home offers rustic feel with luxury comforts & highspeed WiFi, and great indoor & outdoor space. Garage plus add'l parking. Enjoy the area's beaches, restaurants, outdoor activities, breweries & wineries. Southwest Michigan at it's best! Please see policies for pets & children in house rules.

Home in Sawyer

4.96 out of 5 average rating, 78 reviews

Here and Now

Newly renovated home that has been featured in magazines on Interior Design. One of a kind home right next to the Warren Dunes and walking distance to the lake. Beautiful landscaping from every window. Professionally designed home features an upscale interior with a fun twist. Brand new large screened in porch. The perfect spot to enjoy a getaway in style , look no further. 2 separate buildings on the acre property , this rental is for the front building. Wi fi included but can be weak.

Home in Three Oaks

4.82 out of 5 average rating, 96 reviews

Three Oaks Creek House Perfect

3BR, 2 bath contemporary house on Spring Creek--a spawning waterway and spectacular architectural screenhouse (4th BR) at water's edge. Open floorplan, stone fireplace, gourmet kitchen and 4000CDs for spontaneous entertaining. Tempur-Pedic King master BR/office suite with lots of storage and large desk Queen 2nd BR w/standing desk, dresser, books. Full 3d BR w/ 3/4ba en-suite. Wi-fi throughout, Roku, DirecTV with HBO. Spectacular privacy, quiet and tons of specialty ameneties!

Home in Lakeside

5 out of 5 average rating, 57 reviews

Beautiful New Retreat in Lakeside - Walk to Beach

Our sunny Harbor Country home is surrounded by woods at the end of a private street and is walkable to Lake Michigan. 7-day Saturday to Saturday rental only, please. We are a 15-min walk from the Union Pier/Berrien public beach, 5-min drive from New Buffalo & Sawyer, 10-min drive from Three Oaks. There is even a pickleball court outside the front door! Occasional trains only add to the atmosphere. Owners stay on premises in their separate, upstairs studio from time to time.

Home in Three Rivers

5 out of 5 average rating, 7 reviews

Beautiful Family Friendly Beachfront Retreat

This three-bedroom, two-bathroom home sleeps up to 10 people and features a beautiful beachfront with a dock, hammock, and campfire area. Enjoy stunning sunsets from the deck, and dine in the screened-in porch or cook on the gas grill. The fully renovated interior includes all new appliances, a washer/dryer, TV, and Wi-Fi. Just a short drive to town for grocery stores and dining, this tranquil retreat is ideal for escaping the hustle and bustle of city life.

Condo in Stevensville

4.98 out of 5 average rating, 40 reviews

Sunset Pointe Chalet #31: Beach+ Pool + Games

***Superhost*** Book with confidence! This Our privately owned vacation rentals have more then 100 5 star reviews. Book now for an off season getaway or summer of 2025! This Chalet is completely remodeled and has gorgeous panoramic views of Lake Michigan. This unit is in the exclusive beach block section of this fun family resort. Enjoy beautiful sunsets right on your deck! It is a 1 minute walk to the beach and right next to the heated pool!

Cottage in Three Rivers

4.97 out of 5 average rating, 88 reviews

A hideaway retreat on a private lake for relaxing.

An extremely comfortable retreat experience for recharging yourself with water, sun, nature and quiet. This new cottage is on seven secluded acres, ideal for remote working and small reunions. The spring fed lake is wonderful for swimming, kayaking , fishing, pontooning or simply relaxing on the large decks. Kayaks, row boat, paddle boards, and pontoon INCLUDED. Ideal for introducing children to tent camping, wildlife and fishing.

Cabin in Benton Harbor

4.99 out of 5 average rating, 267 reviews

Charming Cabin-Private Beach & Golf

Why the rave reviews? This cabin is a unique and charming 2 bedroom retreat that sits atop a hill and is surrounded by elegantly sculpted terrain of Harbor Shores golf course and walking trails. The private beach on Lake Michigan is steps away. It is located in a quiet neighborhood and is close to family fun activities in St. Joe/Benton Harbor, fantastic restaurants, wine tasting, art galleries and quaint shops.

Home in Benton Harbor

4.98 out of 5 average rating, 136 reviews

Country home near 6 beaches and Harbor Shores Golf

Convenient and close to the following attractions: Harbor Shores Golf Club - 4.9 mi Silver Beach County Park - 7.2 mi Tiscornia Park Beach - 7.0 mi Roadside Park Beach - 5.5 mi Rocky Gap Beach - 4.9 mi Hagar Park Beach - 3.0 mi Riverside Kayak Park - 2.0 mi Opening Fall 2019 Third Coast Paddling - Kayak Rental, Paw Paw River - 5.9 mi Whirlpool Corporation Headquarters - 3.5 mi

Cottage in Three Oaks

4.91 out of 5 average rating, 112 reviews

Private, Sun-filled Union Pier Cottage

Sunny, private cottage set on a half-acre facing woodlands. Quick drive to everything - beaches, hiking, restaurants, wineries, breweries, etc. High-speed internet available and desk with two monitors. Please be advised: reservation requests from first-time AIRBNB renters will be declined. You must have rented through AIRBNB in the past and received a high rating.

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Popular amenities for Diamond Island vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Diamond Island

Home in Berrien Springs

4.95 out of 5 average rating, 120 reviews

Great Living Too

Home in Paw Paw

4.9 out of 5 average rating, 29 reviews

Eagle’s Nest

Cottage in New Carlisle

4.88 out of 5 average rating, 92 reviews

Gram's cottage: Convenient to ND & New Buffalo

Vacation home in Baroda

4.94 out of 5 average rating, 16 reviews

Location location

Home in Benton Harbor

4.88 out of 5 average rating, 40 reviews

Great Escape on Lake Michigan

Home in Benton Harbor

4.75 out of 5 average rating, 12 reviews

Family Getaway

Cottage in Union Pier

4.96 out of 5 average rating, 191 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

Home in Union Pier

4.95 out of 5 average rating, 98 reviews

cozy new buffalo cabin, hot tub, 14m walk to beach

Destinations to explore