Holiday rentals with a pool in St. Joseph

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in St. Joseph

Total holiday rentals
Explore 20 holiday rentals in St. Joseph
Nightly prices starting at
St. Joseph holiday rentals start at £89 per night before taxes and fees
Verified guest reviews
Over 320 verified reviews to help you choose
Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 of St. Joseph holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across St. Joseph rentals
4.9 Average rating
St. Joseph stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated rentals with a pool in St. Joseph

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

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Top guest favourite

The exterior of a two-story gray and green house is showcased, featuring a stone-accented garage and white-trimmed windows. Lush shrubs line the entrance, and a gravel driveway leads to the garage, set against a backdrop of greenery and a clear blue sky.

Home in South Haven

Driftwood Shores-SH is a great fall getaway!

September and Fall is starting to book! 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. NOTE: AirBnb has changed its pricing structure so that now the host pays the 15.5% service fee (instead of the guest.) Your overall cost hasn't changed, but the nightly rate reflects this new payment system.

5.0 out of 5 average rating, 252 reviews

Top guest favourite

A bright living room features high ceilings with a chandelier above a central wooden coffee table. Comfortable dark gray sofas are positioned around the table, complemented by decorative cushions. Large windows allow natural light to fill the space, and a stone fireplace adds a cozy focal point.

Cottage in Union Pier

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, private resort-style neighborhood pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax & 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!

4.97 out of 5 average rating, 247 reviews

Top guest favourite

An inviting outdoor area is featured, showcasing a heated pool beside a vibrant garden filled with blooming flowers. Stylish lounge chairs are positioned near the pool, while a shaded bar area is adorned with ferns and colorful blossoms, creating a relaxing retreat.

Home in South Haven

The Oasis Retreat

The Oasis Retreat is a newly remodeled home with a private heated pool & hot tub, just 4 blocks from downtown South Haven & close to Lake Michigan beaches, marina, trails, restaurants, bars & shops. Perfect for families & groups, the private backyard has an outdoor bar, fire pit, gas grill, pizza oven, ping pong, outdoor shower & detached guest unit w/ seasonal bath/shower. Inside: kitchen, laundry, fast WiFi, Roku TVs, heat/AC, sleeper sofa & upstairs loft. Pool: May-Oct Hot tub: Year-round

4.93 out of 5 average rating, 133 reviews

Guest favourite

This waterfront townhome features a welcoming exterior with a light blue facade and multiple balconies. Lush greenery lines the path leading to the entrance, and expansive windows allow natural light to illuminate the space, creating a peaceful atmosphere in a marina setting.

Townhouse in St. Joseph

Michigan Harbor Townhouse with Marina Views & Pool

** Sun - Sun Rentals preferred ** Luxury waterfront townhome on the marina in Saint Joseph, Michigan w/ pool! A 5 minute drive to 3 separate beaches & downtown for restaurants, wineries, breweries, & shopping. Prime location for Harbor Shores golf course. 2 separate living rooms with televisions on all 3 floors. Beautiful 3rd floor balcony for outdoor dining. 1st & 3rd floor bedrooms have queen mattresses & their own full bathrooms. The primary bedroom has a king mattress with its own ensuite.

5.0 out of 5 average rating, 25 reviews

Top guest favourite

The exterior of a two-story home is visible, featuring a welcoming front entrance. A large tree provides shade, with a swing hanging from one of its sturdy branches. Ferns line the landscape, creating a natural border around the property, complemented by a well-maintained lawn.

Home in St. Joseph

4 Bedroom home w/pool in St. Joseph

This home is all about having fun with the family. Open concept kitchen, living room & dining room. Deck off the dining for eating al fresco. Family room & game room area with large screen TV, Nintendo switch, game table with lots of board games & a dart board. Walkout to the pool (unheated) and fire pit area for fun in the sun and evening campfires to roast marshmallows. Outdoor games include bag toss, ladder ball, ring toss. Home is five miles to Silver Beach and downtown Saint Joseph.

5.0 out of 5 average rating, 114 reviews

Top guest favourite

A three-story cottage with a white exterior and large front porch, situated at the corner of Cavelier Avenue and River Run. The building features bold windows and a classic roofline, surrounded by manicured grass lawns and a well-kept sidewalk.

Home in St. Joseph

Harbor Shores House with Bunk Beds and Pool!

Escape to a tranquil retreat in this 3 bedroom cottage in Harbor Village, where comfort and convenience await. You'll love being situated in the Harbor Shores neighborhood, where downtown St. Joseph and Benton Harbor’s quaint shops and restaurants are just a short walk or bike ride away. The home enjoys stunning views of the marina and golf course from the front porch and terrace accessible via the master suite. Swim and/ or relax at the pool located steps away - right across the street.

5.0 out of 5 average rating, 32 reviews

Guest favourite

Home in Sawyer

Atomic Acres-POOL, Summer 2026 Awaits!

Atomic Acres is a remodeled, 4 bedroom/3,000 sq ft home in the heart of Harbor Country in Sawyer, MI. This home sits on 5 beautiful acres with a fenced in side yard and open back yard with a wandering creek along its border. The amenities are endless: fire pit, seasonal pool & hot tub, patio, ping pong table, pool table, screen porch and more! An aesthetic nod to the mid century era is felt throughout with pieces curated to appeal to the vintage, and all so close to Warren Dunes (1 mile)!

4.96 out of 5 average rating, 102 reviews

Guest favourite

The charming two-story home features a wide front porch with ample seating and decorative lighting. White railings and a wooden design enhance its appeal. Flanking trees provide some greenery, and the entryway is welcoming with its open doors and stylish decor.

Home in Michigan City

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.

4.96 out of 5 average rating, 203 reviews

Superhost

A large outdoor pool is framed by lounge chairs and umbrellas, inviting relaxation under the sun. Adjacent, a bright living area features a blue couch, accent chairs, and a coffee table, with natural light streaming through multiple windows.

Home in St. Joseph

New St Joseph Resort House with POOL

Come enjoy all that Southwest Michigan has to offer in our stylish house in the Harbor Village Resort development, within walking distance to St Joseph with boutique shops, kids museum/carousel/splash pad, and beaches! Relax in the stylish decor in this new 3 br house. Soak up the sun in the large pool right across the street! The Inn at Harbor Shores Resort is also at your doorstep with -Golf - Spa - Plank's restaurant/bar, - Conference center, c - Coffee shop - Marina

4.75 out of 5 average rating, 32 reviews

Guest favourite

An inviting pool area is surrounded by a wooden deck, featuring comfortable seating arrangements and a large red umbrella providing shade. Lush greenery stands tall in the background, complementing the serene atmosphere of the private fenced space.

Home in Lakeside

Lakeside with heated pool & pvt beach access!

LAKESIDE COTTAGE - POOL, HOT TUB & RARE semi-private Lake Michigan access to gorgeous beach shared by just 10 homes, so it’s never crowded! Beach access is a 7-min walk away (no parking). The pool will close Sept 16th, 2027 this year! Charming, sun-filled cottage sleeps 8 (3BR + pull-out). Heated 85 degree pool (May 22–Sept 15), new hot tub, fire pit, gas fireplace, spacious deck, bluestone patio & grill. 10 mins to New Buffalo, Whistle Stop, coffee - just steps away!

4.96 out of 5 average rating, 101 reviews

Guest favourite

Home in New Buffalo

New buffalo Farmstead main home pool hot tub

5 bedroom 2 bath 2200 sq ft modern farmstead , 2 minutes to new buffalo and beach and all its offerings , 18x36 new heated shared pool open 5/20 to 10/ 20 and hot tub open year round maintained at 104 f . Property on 3 acres with plenty of room for kids to play , 26 apple trees and woods , ride host bikes to new buffalo .. Best of both worlds in country , close to town .There’s 1 other home on 3 acre property, this home and 1 guest home ( rented separately) .

4.94 out of 5 average rating, 142 reviews

Guest favourite

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

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

4.84 out of 5 average rating, 202 reviews