Holiday rentals with a pool in St. Joseph

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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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Guest favourite

Home in South Haven

4.99 out of 5 average rating, 180 reviews

Driftwood Shores-Your Base for Fall & Winter Fun!

Book a stay between Nov 1 to March 30, 2025 and check in by 2:30 PM! 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. We are a year round destination!

Guest favourite

Campervan/Motorhome in Porter

4.9 out of 5 average rating, 635 reviews

'Pool Barn Camper' w/Hot Tub near Indiana Dunes

Pool is open! Hot tub open all year! Fully equipped RV is parked in the driveway of our Pool Barn. RV sleeps 5, has bath w/shower, stove, microwave, heat & A/C, & running water all year. We are located minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hiking in the Indiana Dunes National Park along the Little Calumet River and the historic Bailley homestead is only 1 block away. You may also use our large pool, hot tub, grill, campfire, and playground area. No cleaning fee!

Guest favourite

Home in Fennville

4.91 out of 5 average rating, 137 reviews

AlleganOrchardsSleeps25Pool,HotTubFireplaceFirepit

ALLEGAN ORCHARDS: Luxe private retreat 5min. to Saugatuck/Douglas/Fennville Lake MI beaches/sand dunes. - Open kitchen - Private heated pool (fees apply - see house rules) - Private outdoor hot tub (open 24/7/365, no fee) - Indoor fireplace - Outdoor fire pit - Screened porch - Game room: Ping pong, billiards, game table, arcade games - Blue tooth sound throughout - Local area: Saugatuck/Douglas ("Art Coast of MI"), award-winning destination: Restos/Antiques/Boat/Hike/Golf/Wineries/Breweries.

Guest favourite

Villa in Niles

4.96 out of 5 average rating, 104 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. (More photos on socials @stjoeoverlook).

Guest favourite

Apartment in Douglas

4.97 out of 5 average rating, 185 reviews

Cozy condo with fireplace perfect for fall getaway

Beautifully updated vacation with gas fireplace perfect for fall getaway. Close to Lake Michigan and all of the fun activities Saugatuck-Douglas has to offer. Less than 1 mile to Lake Michigan. Close to Douglas and Oval Beaches. Relax on your own front porch or walk a few steps to Isabel’s, a wonderful eatery right on site. One bedroom one bath with a cozy gas fireplace. Additional sleeping for two on pull out couch in the living room. Close to bike path to downtown.

Guest favourite

Cottage in New Buffalo

4.93 out of 5 average rating, 151 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!

Guest favourite

Cottage in Union Pier

4.96 out of 5 average rating, 188 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 favourite

Serviced apartment in Saugatuck

4.94 out of 5 average rating, 179 reviews

1 BR Apt Sleeps 2+ Heated Pool Seasonal

Celebrating our 22nd year as a 5-Star overnight destination in Saugatuck, Michigan. Lake Street Commons Lodging is only a short 4-6 minute walk to Saugatuck's downtown. Centrally located, everything is accessible from Lake Street including the SCA - Saugatuck Center for the Arts with downtown Douglas only a 10-13minute walk across the bridge. Bring your camera because the early morning and evening shimmers on the waters of Lake Kalamazoo harbor are magic.

Guest favourite

Home in New Buffalo

4.92 out of 5 average rating, 302 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 .

Superhost

Home in South Haven

4.84 out of 5 average rating, 174 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 favourite

Barn in Hamilton

4.95 out of 5 average rating, 112 reviews

The Garden House Cottage at Redbud Farm

It's summer at Redbud Farm! The Garden House Cottage is a beautifully remodeled old farm barn. Modern boho farmhouse style. This place has charm galore. You'll love the peace and quiet of the country and the gardens are professionally landscaped and maintained. Enjoy the views of the English potager style garden right out the window while relaxing on the queen bed. Traveling with friends/family? Check out my other listing The Granary at Redbud Farm.

Guest favourite

Guest house in Cassopolis

4.98 out of 5 average rating, 122 reviews

2 person 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 cows, sheep, & chickens roaming the pasture. We also have a cat that claims the pool area as her 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.