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.

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Guest favorite

Cottage in New Buffalo

4.95 out of 5 average rating, 39 reviews

Luxury Cottage with pool; summer will book fast

The madrona cottage is the perfect vacation home. You will fall in love with the cottage and the location, New Buffalo is amazing. The home has 4 full bedrooms and 3.5 baths. It will sleep 8 guests easy. Everything you need to enjoy a nice vacation is included in the place. The cottage has been completely rehabbed with all spaces being brand new. It's has a heated pool and is close to the beach. Relax by the fire or enjoy the game room with a pool table, card table and games. Great for families.

Guest favorite

Home in Stevensville

5 out of 5 average rating, 52 reviews

Guest favorite! Quiet setting w/heated pool & more

Welcome to our SW Michigan retreat! This freshly updated home in a quiet country setting feels far away from it all but is close to everything Harbor Country has to offer including beaches, dunes, breweries & shopping. With 5 bedrooms & 3.5 baths, there's enough space for your large family or multiple families to relax & enjoy plentiful amenities including heated pool (seasonal), hot tub, trampoline, fire pit, large yard, multiple outdoor dining areas, woods with paved walking path, WiFi & more!

Guest favorite

Home in Holland

4.95 out of 5 average rating, 105 reviews

The Splash Pad- a secluded pool/hot tub oasis

The Splash Pad is a perfect getaway for families and groups. Our goal is to bring people together for quality time so we created spaces that everyone will love: the (non heated) pool, hot tub, patio, volleyball net and horse shoes, fire pit, indoor gas fireplace, and a spacious living room with a 55in TV. We hope you explore all the local attractions like: beaches, shops, restaurants, breweries, and hiking trails- all within 4 miles of The Splash Pad! Just added a Level 2 EV charger!! Available

Guest favorite

Home in South Haven

4.91 out of 5 average rating, 47 reviews

The Oasis Retreat

The Oasis Retreat, located right outside downtown South Haven, is perfect for year round adventures & only 4 block walk from downtown. Newly remodeled, it boasts a heated pool, hot tub, outdoor bar, backyard, 2nd unit, & fire pit. Ideal for families it includes Wi-Fi, kitchen, laundry, ring, patio, outdoor shower, outhouse, & more. If dates are unavailable, consider our nearby properties: 1) https://www.airbnb.com/slink/PSGEaadD 2) https://www.airbnb.com/slink/R5t9UwVU Pool: May - October

Guest favorite

Guesthouse in Porter

4.9 out of 5 average rating, 740 reviews

'Pool Barn' w/Games & Hot Tub near Indiana Dunes

Pool and hot tub are open! The Pool Barn offers a great location & unique experience. 1 hour from Chicago & less than 10 minutes from large sand beaches & hiking trails of Indiana Dunes National Park & Indiana Dunes State Park. Lots to do at the 'Pool Barn' too. Outside is pool, hot tub, grill, firepit, playground, & we are on hike/bike trail. Inside is billiards, ping pong, air hockey, darts, popashot, foosball, board games, large smart tv, 6 beds, couch, & full kitchen. No cleaning fee!

Guest favorite

Home in Chesterton

4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

Open-concept home with a private heated pool. Take a hike, climb a dune & run back down to the lakeshore in downtown Chesterton, a perfect getaway weekend at the Indiana Dunes. Fenced yard, grill, and cozy fire pit. Local markets, festivals, orchards, and farms. Just a few miles from the beach and national park. Saturday's European Market offers a wonderful healthy, fun, entertaining shopping & dining experience for all. Fresh produce, food trucks, mimosa brunches, and candy shops.

Superhost

Condo in Saugatuck

4.9 out of 5 average rating, 153 reviews

Robyn's Nautical Nest #6 at ♥️of Downtown Saugatuck

This nautical nesting spot lands you at the water’s edge, surrounding you with downtown Saugatuck best attractions, all within walking distance.! Guests also enjoy included seasonal access (May-Oct 7/2024) to the Ship n Shore Hotel pool & hot tub! Enjoy poolside service from the BARge, while taking in the best boat watching traffic in town! You are just steps away from boarding the Star of Saugatuck paddle boat, Saugatuck Chain Ferry and everything else Saugatuck has to offer!

Guest favorite

Cottage in South Haven

5 out of 5 average rating, 20 reviews

Pool & hot tub, Lake MI access, theatre room

Amazing home built in 2020 has so many qualities in a great location. Lake Michigan private neighborhood beach access by a tram (elevator to beach), heated pool & hot tub surrounded by a deck & patio. Check out the 5 bedrooms with 2 master suites, 2 living areas, 4 flat screens, a spectacular screened in porch that includes dining & fire table with sectional seating. Enjoy a stocked kitchen, game, theatre & bunk rooms, swing set, fire pit make this home an easy pick!

Guest favorite

Home in St. Joseph

4.96 out of 5 average rating, 24 reviews

Poolside Oasis - Private Heated Pool + Fun Games

Escape to our stunning 4-bed, 1.5-bath home with a private in-ground pool! Bright living spaces, a fully equipped kitchen, cozy bedrooms, and an amazing pool await. Conveniently located near charming Saint Joseph, Michigan, with Lake Michigan's sandy shores and vibrant downtown nearby. Indulge in local cuisine, explore nature trails, then return to the comfort of our inviting home. Your ultimate vacation experience awaits! Book now for an unforgettable getaway!

Guest favorite

Cottage in Union Pier

4.96 out of 5 average rating, 190 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, pool, 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 and create lasting memories!

Guest favorite

Cottage in New Buffalo

4.96 out of 5 average rating, 100 reviews

Casa Playa New House w/ Private Spa & Pool Access

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!

Superhost

Home in Lakeside

4.8 out of 5 average rating, 10 reviews

New renovated house, private heated pool sleeps 10

Experience Lakeside luxury in our newly renovated 4BR/2BA house with a brand new pool, patio, and stunning indoors, and beautiful landscaping. Sleeps 10 with a private heated pool, fire pit, BBQ, and Flat screen TVs. Just minutes from Union Pier beach, and close to brew-pubs, wineries, restaurants, and golf. Book now and enjoy a dream vacation!