Holiday rentals with a pool in St. Joseph

5 out of 5 average rating, 203 reviews

The exterior of the cottage features vibrant blue siding and a covered porch with white railings. Lush greenery and landscaped beds surround the entrance, creating a serene and welcoming façade. A pathway leads to the front door, inviting guests into the home.

Home in New Buffalo

Designer Cottage - walking distance to downtown

Dream cottage getaway just over an hour from downtown Chicago. Walking distance from the beach, restaurants and all of downtown New Buffalo. Close to the casino, wineries and breweries. Whether driving in or taking the train, The Bradford is a relaxing yet sophisticated getaway. Eat, drink, and enjoy the beach, the pool, the shops and incredible summer sunsets, all within walking distance! Please note pool/bathhouse open late May - September and is shared with our association.Permit C22-0051

An enclosed indoor pool area features a large, clear swimming pool surrounded by spacious tile flooring. Illuminated by natural light from the ceiling, several lounge chairs are positioned at the poolside, providing a relaxing atmosphere for guests.

4.97 out of 5 average rating, 104 reviews

The Northern Anchor: Your Perfect Getaway!

The new enclosed subdivision pool & hot tub are now open! Enjoy our beautiful vacation house. Fully furnished with loads of thoughtful details. Perfect for families with kids or for groups/individuals looking for a relaxing get away. Close to everything: beaches, downtown shopping, wonderful restaurants, award winning golf courses, pick your own orchards, beautiful wineries and much more. Visit us year round - from snowy woods to sandy beaches - the Northern Anchor has something for everyone.

Superhost

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, 135 reviews

Harbor Country Charm w Heated Pool Open Til 10/12!

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.

4.96 out of 5 average rating, 184 reviews

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.

4.95 out of 5 average rating, 105 reviews

An outdoor firepit area is surrounded by teal-colored Adirondack chairs, creating a cozy space for gathering. The house features multiple windows illuminated at dusk, highlighting its charming architecture, while trees provide a natural backdrop, enhancing the outdoor setting.

Home in New Buffalo

NB Getaway w/HotTub,Pool,BBQ & Priv Screening Room

Richly designed 6BR/5BA home near New Buffalo Harbor and beaches. Great Room with stone fireplace. Chef’s kitchen with marble-top island. 3-season sunroom. Elegant, comfy furniture. Primary BR with stone fireplace, twin sinks, tile walk-in shower, and jacuzzi. Lower-level Guest BR with fireplace, full BA, game room, and screening room. Second floor features loft space, 3 BRs, 2 BAs, and a Mother-in-Law Suite with kitchen. Smart TVs in 5 BRs. BBQ deck, firepit patio, and hot tub.

4.96 out of 5 average rating, 225 reviews

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, 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!

4.97 out of 5 average rating, 126 reviews

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

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.

4.85 out of 5 average rating, 197 reviews

A spacious green house features a traditional design with multiple windows on the upper level, bordered by well-maintained landscaping. A large driveway extends in front, accommodating parking for several vehicles, leading to a three-car garage with white doors.

Home in Union Pier

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 .

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.

5 out of 5 average rating, 226 reviews

Driftwood Shores-Thanksgiving in South Haven!

South Haven is a great place for a Fall or Winter getaway! 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.

4.98 out of 5 average rating, 173 reviews

A fenced-in pool area features a clear water pool surrounded by a concrete deck. Lounge chairs and a dining set are positioned nearby, while a red umbrella offers shade. A slide is visible in the pool, with cornfields extending in the background under a cloudy sky.

Guesthouse in Cassopolis

Couples cottage with 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.

4.93 out of 5 average rating, 135 reviews

A rustic cabin is embraced by lush greenery, featuring warm wooden siding and a welcoming porch. Several large windows allow natural light to illuminate the interior. Landscaping with a variety of bushes and stones enhances the inviting outdoor setting.

Cabin in Saugatuck

Heavenly 7 Retreat Luxury Cabin -Kingfisher Cove

Our cozy 3 bedroom, 2.5 bath luxury rustic cabin features all the comforts of home and more. Fully furnished for your comfort with towels, linens and other necessities. This cabin sleeps 8 comfortably. A heated pool and lake access are available from Memorial Day to mid September. Full-size washer & dryer in the cabin for your convenience. For larger groups, ask about availability to also rent one of our affiliated cabins nearby.

4.91 out of 5 average rating, 373 reviews

A fire pit is surrounded by four teal Adirondack chairs, set on a grassy area. A warm fire burns brightly in the center, with two serene ponds visible in the background, framed by trees and inviting outdoor space.

Cabin in Benton Harbor

50 Private Acres w/ Trails & Pool: Cozy Cabin

Unwind in this freshly renovated cabin set on 50 acres of peaceful nature. Explore private walking trails, relax by two serene ponds, or cool off in the seasonal pool (shared with our family). The space includes a kitchen for cooking, Xbox One for movie nights, and a fire pit perfect for stargazing. Dog-friendly and ideal for a quiet escape into the outdoors—with all the comforts of home.

Popular amenities for St. Joseph rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 27 reviews

A modern kitchen is presented with sleek white cabinetry and stainless steel appliances. An island with bar stools is centered, complemented by pendant lighting. Large windows offer a view of the outdoor area, allowing natural light to enhance the space.

Home in New Carlisle

Luxury home with pool.

The outdoor area features a sparkling pool surrounded by lounge chairs and umbrellas. A spacious patio is equipped with a large dining table and additional seating, offering a perfect setting for relaxation in a beautifully landscaped backyard.

4.95 out of 5 average rating, 20 reviews

Lamb Guest | Private Pool, Hot Tub, Cabana, Dogs

5 out of 5 average rating, 38 reviews

Luxury Lake Michigan Escape w/Spa. Holiday ready!

4.92 out of 5 average rating, 115 reviews

The exterior of a multi-level house is depicted, featuring a combination of siding and stone accents. Large windows are present, along with balconies on the upper levels. A paved driveway leads to a garage, surrounded by greenery and a clear blue sky.

Home in Michigan City

Beautiful home with Beach views in Beachwalk

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.

4.83 out of 5 average rating, 185 reviews

Experience Nature-Charming Cottage

4.95 out of 5 average rating, 78 reviews

A swimming pool is situated in an outdoor space with a concrete deck. Two lounge chairs are positioned beside the pool. Inflatable rings float in the water. Sun umbrellas provide shade over seating areas equipped with a barbecue grill in the background, set against lush greenery.

Home in Sawyer

Atomic Acres-Harbor Country Fall Awaits!

4.91 out of 5 average rating, 309 reviews

A game room features a multi-game table for pool, air hockey, and ping pong, surrounded by comfortable bean bag seating. Bright, geometric lighting enhances the space, while classic arcade machines and a large wall Connect 4 game add fun to the cozy environment.

Home in South Bend

Hot Tub | Backyard Oasis | Game Room | |Coffee Bar

4.83 out of 5 average rating, 83 reviews

An indoor pool area features a bright, open design with vaulted wooden ceilings and intricate skylights. Surrounding the pool, large windows provide natural light, complemented by tiled flooring. Comfortable seating is positioned nearby, creating a relaxing and inviting atmosphere.

Home in Union Pier

Fabulous Heated Indoor Pool & Tennis Court!

Condo rentals with a pool

5 out of 5 average rating, 15 reviews

Condo in Saugatuck

Waterfront condo -pool-beach-bike-hike-shop-chill

5 out of 5 average rating, 20 reviews

An indoor swimming pool is framed by large windows allowing natural light to fill the space. Comfortable chairs are positioned around the pool area. A shallow section with stairs is visible, alongside a section designated for lounging. The ambiance is relaxed and welcoming.

Condo in South Haven

Lake Effect Loft +Beach+Downtown+Pool+Hot tub

Superhost

A screened-in porch features a wooden circular table accompanied by four matching chairs. A cozy seating area with blue cushions and decorative pillows is also present. Natural light filters through the surrounding trees, enhancing the serene atmosphere.

Condo in Union Pier

4.73 out of 5 average rating, 11 reviews

Union Pier Condo with Association Heated Pool.

4.93 out of 5 average rating, 54 reviews

The open-layout living area features a cozy sofa facing a gas fireplace, with two green armchairs positioned nearby. Large windows allow natural light to fill the space. A colorful wall art piece adds a touch of design, complemented by a coffee table with magazines.

Condo in Douglas

Northern Lights 2 Bed 2 Bath With Pool

5 out of 5 average rating, 24 reviews

Condo in South Haven

South Haven North Shore condo

4.97 out of 5 average rating, 35 reviews

A spacious deck is shown, featuring a wooden table with an umbrella and string lights illuminating the area. The view of the ocean is visible in the background, with a sunset casting soft colors in the sky. The side of the building is also visible, with multiple windows.

Condo in Coloma

Amazing Beach Condo with pool and great sunsets!

4.91 out of 5 average rating, 33 reviews

A spacious kitchen features warm wooden cabinetry and an expansive granite countertop. A round breakfast bar with stools provides seating, and modern appliances, including a refrigerator, are visible. Natural light floods the area through multiple windows, enhancing the inviting atmosphere of the space.

Condo in Saugatuck

Birds Nest | 2BR | Downtown Saugatuck

4.97 out of 5 average rating, 232 reviews

A spacious living area features a brown leather sofa adorned with colorful pillows. A wooden coffee table is placed in front. A mounted television is positioned above a cozy gas fireplace, complemented by blue walls and natural light filtering through white shutters. A small dining area is visible in the background.

Condo in Douglas

Cozy condo with fireplace perfect for fall fun.

Other holiday rentals with a pool

5 out of 5 average rating, 10 reviews

A comfortable bedroom features a spacious bed adorned with an orange and white quilt, accented by multiple pillows. A large wall print depicting a marina sunset creates a serene backdrop. Soft lighting is provided by wall sconces, and a woven basket of fruits sits on the bed.

Townhouse in South Haven

Harbor Escape

5 out of 5 average rating, 27 reviews

A serene saltwater pool is highlighted, surrounded by a spacious deck furnished with lounge chairs and umbrellas. A cozy pool house is visible in the background, framed by lush greenery and trees, providing a tranquil outdoor setting.

Home in Sawyer

Las Moras, 6 Acres & Large Pool

4.9 out of 5 average rating, 39 reviews

An inviting winter igloo features a cozy seating area with plush blankets draped over a light-colored sofa. A small fire burns atop a black stand, while two glasses of red wine rest on a modern circular table alongside a jar filled with treats.

Home in Baroda

The Grapes are Calling - heart of SW MI

4.96 out of 5 average rating, 69 reviews

An open-concept living space features large windows with natural light illuminating the room. A spacious kitchen with dark wood cabinetry is visible in the background, complemented by a long dining table. A comfortable sofa with decorative pillows faces the seating area, promoting relaxation.

Apartment in South Haven

Old School Condo/Loft in South Haven

Holiday home in South Haven

A spacious outdoor patio area is furnished with comfortable seating and a table. An umbrella provides shade, while the surrounding greenery enhances the tranquil ambiance. A view of the marina is visible through the glass railing, inviting relaxation and social gatherings.

5 out of 5 average rating, 79 reviews

Blue Shore @MarinaResort Waterview/Pool/SunRoom

4.88 out of 5 average rating, 25 reviews

The exterior of a classic farmhouse is showcased, featuring a heated in-ground pool with clear blue water. A spacious deck is furnished with seating and an umbrella. The house has a two-story structure with multiple windows, allowing for natural light to brighten the surroundings.

Home in Sodus Township

Modern Farmhouse w/ Pool Near St Joe

5 out of 5 average rating, 10 reviews

The Glass House is situated amidst vibrant autumn foliage, showcasing a modern design with expansive glass walls and a stone façade. The surrounding lawn features fallen leaves and natural wooden elements, with outdoor seating options visible on the terrace.

Home in Valparaiso

A Glass House in a Gated Nudist Resort