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Holiday rentals with a pool in St. Joseph

Find and book unique homes with a pool on Airbnb

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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Cabin in Benton Harbor

4.91 out of 5 average rating, 290 reviews

Cozy Cabin by Nature

We deep clean and sanitize after every guest. Enjoy social distancing in this completely renovated cabin in a picturesque setting with 2 ponds. Dog friendly. A full kitchen to cook your own meals. Xbox one is provided to watch movies and relax. Enjoy outdoors with the fire pit. We are dog friendly. We do ask 3 things if you bring your furry family with you. Please keep them off the furniture, clean up after their business and keep them leashed when around other guests as the property is shared

25 Jun – 2 Jul

$501 SGD per night

Guest favourite

Home in St. Joseph

5.0 out of 5 average rating, 11 reviews

Brand new St Joseph Resort House with POOL

Come enjoy all that Soutwest Michigan has to offer in our stylish new 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 brand 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, a spa, upscale Plank's restaurant/bar, conference center, coffee shop, and marina access.

27 May – 3 Jun

$546 SGD per night

Guest favourite

Home in South Haven

4.99 out of 5 average rating, 150 reviews

Driftwood Shores: Book a May weekday, great rates!

Come May 5-9 for Holland Tulip Festival! Enjoy a trip to beautiful South Haven along the shores of Lake Michigan. Driftwood Shores is a charming 1,680 square foot home in the Harbor Club Resort. It has everything you need to enjoy a peaceful family vacation, friends getaway, or girls weekend out. The Resort's Indoor Pool with retractable roof & outdoor hot tub, (see photos), is open from 7 AM to 10 PM. It is included with your stay. Driftwood Shores, a year round destination!

13–20 Nov

$361 SGD per night

Guest favourite

Home in Three Oaks

4.9 out of 5 average rating, 103 reviews

Luxe Life | Heated Pool | Hot Tub| Sleeps 10

Important notes: - Home is in HARBERT by the lakefront, NOT in Three Oaks - Hot tub open all year - Pool closed from October 23, 2023 through Memorial Day 2024 After a day of exploring Lake Michigan, Warren Dunes, or New Buffalo (just a quick 10-minute drive away), 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 cap off the evening around the fire pit while toasting marshmallows.

15–22 Oct

$1,001 SGD per night

Guest favourite

Serviced apartment in New Buffalo

5.0 out of 5 average rating, 16 reviews

Charming 1BR/1BA Retreat with private beach access

This airy space holds warmth in the details — wooden accents, walls the color of pine and sage, the faint smell of a campfire. One king bed features a cushy Casper mattress topped with plush Sferra linens. The bathroom, complete with Malin+Goetz bath products, keep things fresh. A small but mighty kitchenette is home to your morning coffee thanks to a Moccamaster coffee machine, fridge + microwave. If you must remain connected to the real world, the WiFi and TV are solid.

30 Jan – 6 Feb

$181 SGD per night

Guest favourite

Cottage in New Buffalo

4.94 out of 5 average rating, 141 reviews

Perfect Get Away - Private Hot Tub - Lots of Room

Gorgeous, New Buffalo cottage in the heart of New Buffalo. Perfect for families and friends ~ many areas for gathering within the home. Private hot tub off the back screened in porch and only ten steps away from large community pool. Walk to everything in NB - Whittaker is only 2 blocks away. Enjoy close proximity: beach, amazing restaurants in town (Stray Dog, Redamak's, etc.). The private hot tub makes this perfect place for social distancing with Family!

15–22 Dec

$932 SGD per night

Guest favourite

Cottage in Union Pier

4.96 out of 5 average rating, 173 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!

14–21 Feb

$795 SGD per night

Guest favourite

Home in New Buffalo

4.91 out of 5 average rating, 270 reviews

Farmesque with a splash of modern

Turn back time with trough sinks and claw foot tub and cedar beams ,distressed floors and walls with a mix of modern. Galien river marsh across street full of nature and several bikes on property for your riding pleasure . Newly built 2019 , 3 blocks from Main Street downtown New Buffalo.6 blocks from beach , enjoy all local spots and coffee shop and grocery steps away . Dead end street in very quaint neighborhood, covered front porch enclosed rear porch .

4–11 Mar

$319 SGD per night

Home in South Haven

4.85 out of 5 average rating, 157 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

19–26 Sep

$542 SGD per night

Guest favourite

Guest house in Cassopolis

4.97 out of 5 average rating, 101 reviews

Cottage with pool & hot tub for two!

Come for a relaxing getaway in the country. Cook in our small kitchenette or use our pellet grill or fire pit. Located in a small hobby farm setting with cows, sheep, & chickens roaming the pasture. We also have 3 kittens 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 soak in the hot tub and let the worries of life melt away during your stay.

14–21 Nov

$255 SGD per night

Guest house in Michigan City

4.87 out of 5 average rating, 121 reviews

Lagunitas Coach House in Beachwalk, Lake Michigan

Lagunitas Coach House is a sought after location on the quaint Thomas blvd cul de sac. It is the coach house to Gooch Life. It is the perfect get away spot for a couple or small family wanting to escape to the beautiful beach of Lake Michigan. Lagunitas and Gooch Life share the property but are separate structures. Lagunitas has a private entrance, amenities, and parking. Lagunitas sleeps 6, see pictures for bed configuartion.

5–12 Oct

$253 SGD per night

Tiny home in Sawyer

4.8 out of 5 average rating, 122 reviews

After Dune Delight

We are located in a small Tiny Home park. Full kitchen, sleep up to 6. Directly across street from Warren Dunes State Park. Wineries, breweries all within easy driving distance. Beach Bucket Ice cream shop next door. Walk and bike back to dunes for free. Come and relax with us! After Dune Delight is unit #18.

6–13 Sep

$217 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for St. Joseph rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Michigan City

4.97 out of 5 average rating, 153 reviews

5 Bedroom Luxury Home In Heart of Beachwalk Resort

19–26 Oct

$483 SGD per night

Guest favourite

Home in Fennville

4.97 out of 5 average rating, 181 reviews

FennWoods - A Modern, Wooded Retreat

8–15 Jul

$784 SGD per night

Guest favourite

Home in Saugatuck

4.97 out of 5 average rating, 260 reviews

Castlewoods

27 May – 3 Jun

$1,008 SGD per night

Guest favourite

Home in Fennville

4.9 out of 5 average rating, 124 reviews

ALLEGAN ORCHARDS: SLEEPS 25, WEDDINGS, POOL,HotTub

14–21 Apr

$757 SGD per night

Guest favourite

Home in Douglas

4.97 out of 5 average rating, 117 reviews

Rustic Mid Century Pool Oasis. Steps from town!

13–20 Dec

$636 SGD per night

Guest favourite

Home in St. Joseph

5.0 out of 5 average rating, 42 reviews

Beautiful 4 Bedroom home w/pool

1–8 Oct

$748 SGD per night

Guest favourite

Home in Bridgman

5.0 out of 5 average rating, 60 reviews

Charming Bungalow | Heated Pool | Huge Fenced Yard

13–20 Dec

$304 SGD per night

Home in St. Joseph

4.92 out of 5 average rating, 12 reviews

Poolside Oasis - Private Heated Pool + Fun Games

30 May – 6 Jun

$711 SGD per night

Apartment rentals with a pool

Guest favourite

Apartment in Douglas

4.97 out of 5 average rating, 151 reviews

Fun bright condo with pool only steps away

20–27 Sep

$339 SGD per night

Guest favourite

Apartment in Saugatuck

4.91 out of 5 average rating, 147 reviews

Robyn's Top Notch Nest#7 Top Floor@ ♥️of Saugatuck

7–14 Jan

$315 SGD per night

Guest favourite

Apartment in Coloma

4.93 out of 5 average rating, 67 reviews

Anchor on Arbor:Lakeside Condo w/Pool+Beach Access

17–24 Aug

$350 SGD per night

Guest favourite

Apartment in Stevensville

4.97 out of 5 average rating, 30 reviews

Sunset Pointe Chalet #31: Beach+ Pool + Games

25 Nov – 2 Dec

$449 SGD per night

Apartment in South Haven

4.92 out of 5 average rating, 12 reviews

Sunny South Haven Condo < 1 Mi to Beaches!

29 Oct – 5 Nov

$310 SGD per night

Apartment in South Haven

4.89 out of 5 average rating, 19 reviews

Beautiful North Shore Studio

22–29 Jun

$297 SGD per night

Guest favourite

Apartment in South Haven

4.91 out of 5 average rating, 22 reviews

Beach More, Worry Less at Harborside Oasis

11–18 Feb

$433 SGD per night

Guest favourite

Apartment in South Haven

5.0 out of 5 average rating, 12 reviews

Private Beach/Pool on Lake MI Condo

18–25 Aug

$399 SGD per night

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

Total rentals
20 properties
Popular amenities
Kitchen, Wifi and Pool
Wifi availability
20 properties include access to wifi
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
200 reviews
Nightly prices starting at
$244 SGD before taxes and fees

Destinations to explore