Vacation rentals with a pool in Benton Harbor

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Benton Harbor

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

The dining area features a modern table surrounded by black chairs, with large windows offering views of the serene private lake outside. Natural light fills the space, highlighting the open layout that connects to the outdoor seating area.

Home in Stevensville

4.95 out of 5 average rating, 59 reviews

Bright & Modern Home with NEW POOL (open May-Sep)

The modern architecture and bright and airy design of the home provides a relaxing, inviting and luxurious space for guests. The home: -is set on an a sandy lot, facing a small private lake -has 3 bedrooms, 3 bathrooms, a den and a loft -has an 8-person hot tub and private pool -is equipped with top of the line kitchenwares -includes outdoor amenities such as kayak, canoe, fire pit, grill, yard games (Jenga and corn hole), etc. -allows pets but must be included in the booking and pay a pet fee

Top guest favorite

Home in South Haven

5 out of 5 average rating, 214 reviews

Driftwood Shores-Still some Sept. weekdays open!

It's time to start thinking about the fall! Great September weekday rates! How about a golf trip? Enjoy a trip to beautiful South Haven along the shores of Lake Michigan. Driftwood Shores is a charming 1,680 sq. ft. home in the Harbor Club Resort. It has everything you need to enjoy a peaceful family vacation, friends getaway, or girls weekend out. The Resorts Indoor/Outdoor Pool with retractable roof and outdoor hot tub is open year around from 7 AM to 10 PM. It is included with your stay.

Guest favorite

A repurposed barn is visible beyond the in-ground pool, framed by lush greenery. The structure features a blue door and multiple windows, inviting natural light. A bright sky with scattered clouds creates a serene backdrop for the tranquil setting.

Barn in Benton Harbor

4.94 out of 5 average rating, 82 reviews

Updated Pool House with Private Pickle Ball Court

Ideal for families this is the perfect escape from city life. Our repurposed barn is a unique "Glamping" adventure, wake up to the crow of our roosters and enjoy fresh eggs every day. Just outside of St Joe & Benton Harbor, enjoy your stay in this repurposed old hatchery with exclusive use of the in-ground pool. Take advantage of the 30 acres surrounded by a creek & river or make us your home base for exploring the wineries, golf courses, hiking trails & beaches in the surrounding area.

Guest favorite

A stone pathway leads through lush greenery and colorful flowerbeds toward a light-filled, glass-fronted structure. Towering trees create a natural canopy, enhancing the serene atmosphere of the garden setting.

Home in Three Oaks

4.88 out of 5 average rating, 129 reviews

Harbor Country Charm w Heated Pool & Hot Tub

Important notes: - Home is in HARBERT by the lakefront, NOT in Three Oaks - Hot tub open all year - Pool closes October 10, 2024 through Memorial Day 2025 After a day of exploring the waters of Lake Michigan, Warren Dunes, or nearby wineries, find your sanctuary at Mae's Place. Recharge by soaking in the inviting hot tub, sizzle up a delicious meal on the grill or in the kitchen and end the evening roasting marshmallows around the fire pit or watching an outdoor movie on the pool deck.

Guest favorite

A large outdoor pool features clear blue water surrounded by a spacious deck equipped with numerous lounge chairs. Sunlight reflects off the surface, highlighting the inviting atmosphere, with nearby buildings visible in the background.

Home in Michigan City

4.96 out of 5 average rating, 181 reviews

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Beautiful home in the heart of Beachwalk, across the street from Lake Kai, pools, basketball & tennis courts and 2 blocks to Lake Michigan. This home is bursting with charm. Front porch runs the width of the house. Dining area opens up to family room with a lovely fireplace. Stunning master bedroom w/walk-in closet and beautiful new bathroom with all the finishes. 3 more bedrooms upstairs, one with full bathroom attached and the other 2 sharing bathroom. 5th bedroom on the lower level.

Guest favorite

An inviting outdoor pool area is surrounded by lounge chairs arranged along the deck. Trees provide natural shade nearby, and a cozy pool house is visible in the background. The crystal-clear water of the pool invites relaxation and enjoyment.

Cottage in Union Pier

4.96 out of 5 average rating, 214 reviews

Designer Cottage Relax Pool Beach & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, community pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax and unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today! Create lasting memories!

Guest favorite

An aerial view showcases the spacious outdoor area, featuring a blue tennis court adjacent to a rectangular pool surrounded by lounge chairs. Lush greenery and trees frame the property, while a well-maintained lawn offers additional recreational space.

Villa in Niles

4.97 out of 5 average rating, 121 reviews

Pool, Hot tub, Kayaks, Waterfront, SW Michigan

Waterfront property with a private hot tub, pool, and tennis court, making it an ideal destination for those seeking both relaxation and recreation. Visit beautiful Southwest Michigan and stay at the St. Joe Overlook. Take a swim in the pool, unwind in the hot tub, take the kayaks out for a river cruise, or sit by the fire. Enjoy this stunning location and top-notch amenities. A trip to the St Joe Overlook is the perfect place to gather & reconnect. Maximum Guest Count 16.

Superhost

The exterior of the cottage showcases a modern design with a light-colored facade and a stylish metal roof. Surrounded by lush greenery, the property features multiple windows that invite natural light. A spacious deck extends from the house, providing additional outdoor living space.

Home in Union Pier

5 out of 5 average rating, 3 reviews

The Fern: 2BR, Hot Tub, Fire Pit, Walk to Beach

Presenting Townie 4 - The Fern, part of the unique Townie Cottages collection. This newly built lakeside luxury home was designed exclusively by Kate Marker Interiors (recognized by Architectural Digest and Luxe Home). Located in Union Pier, these exquisite cottages blend rustic charm and modern elegance for an unforgettable stay. Immerse yourself in a meticulously curated interior with high-end finishes and chic furnishings, creating a sophisticated yet homey atmosphere.

Superhost

Home in Union Pier

4.84 out of 5 average rating, 186 reviews

New Buffalo / Union Pier Pool Hot tub 6 Bedroom

Relax with the whole family at this peaceful home with Classic European style meets Lake Michigan! This astonishing turnkey home is the perfect escape from life in the busy city. The home is ideal for entertaining Famliy . 5 bed , 4 bath , hot tub and gas grille and( pool opens June 6) close to union pier beaches and wine country . Property is nestled in a quaint country road location 1/2 mile off re arrow highway. Room for 10 cars,blue stone patios,ping pong table .

Superhost

A secluded in-ground pool is surrounded by lush greenery and landscaped gardens. Several lounge chairs are arranged near the pool, which reflects the sky above. Flowering plants and shrubs frame the scene, creating a peaceful outdoor retreat.

Home in South Haven

4.84 out of 5 average rating, 181 reviews

Experience Nature-Charming Cottage

Romantic getaway and/or family adventure Quiet updated farmhouse on a quiet road 5 miles from South Haven and Lake Michigan.The Black River runs along the property and there are 3 ponds.There is secluded in ground pool,woods and landscaped grounds for walks Great local markets A guest made a video about his time at the cottage that you can see on You Tube. GoozyVision Trip to South Haven,Michigan July 2017 The video also shows the beach and the town

Guest favorite

A serene association pool is surrounded by lush greenery, providing a tranquil setting for relaxation. The pool features a shallow end with a depth of 3 feet and includes stainless steel handrails for easy access. Sunlight reflects off the water, enhancing the natural surroundings.

Cottage in New Buffalo

4.96 out of 5 average rating, 110 reviews

Casa Playa - Union Pier Home w/ Pool & Private Spa

This 4 bedroom getaway is located in the heart of Harbor Country and is just a 10 minute walk or 3 minute drive to the best beach in Union Pier! Casa Playa has EVERYTHING a vacation house can offer: an association POOL, a private HOT TUB, high speed internet that accommodates many people working from home, a cozy indoor fireplace, an outdoor fire pit, an outdoor deck & grill, 2 smart Tvs, ALL brand new appliances, and games for the whole family!

Top guest favorite

An aerial view showcases a fenced-in pool area surrounded by lush green lawns and mature trees. A small patio with outdoor seating is visible beside the pool. The gravel driveway leads to the property, with an adjacent structure and a pergola enhancing the outdoor space.

Guesthouse in Cassopolis

4.98 out of 5 average rating, 161 reviews

Quiet cottage with pool and hot tub!

Come for a relaxing getaway in the country. Cook in our small kitchenette or use our Blackstone or fire pit. Located in a small hobby farm setting with sheep roaming the pasture. We also have a couple cats that claim the pool area as their own. The long driveway and gravel road are perfect for a leisurely stroll to enjoy the great outdoors. Take a swim in the pool or a soak in the hot tub and let the worries of life melt away during your stay.