Vacation rentals with a pool in St. Joseph

4.98 out of 5 average rating, 102 reviews

A bedroom features a spacious bed adorned with white linens and a navy throw blanket. Exposed brick walls add character, complemented by framed ocean-themed art. A mirrored dresser and a closet with hanging space provide ample storage. Natural light filters through a nearby window.

Apartment in South Haven

Walk everywhere: Bikes: Pool & hot tub: Beach gear

✨Upscale historic loft building 🚶WALK EVERYWHERE 🕑 2:00 PM CHECK-IN ⭐️Central Loft amenities⭐️ ♨️ Hot tub 🏊‍♂️ Indoor heated pool 🎬 2 movie theaters 💪 Workout room 🏖️ Beach necessities included 🌊 1/2 mile to Lake Michigan 🚲 4 beach cruiser bikes included 🛍️ A block from downtown SoHa 🍷 Near The Lakeshore Wine Trail 🍺 Close to several breweries 🧺 Washer & dryer in condo ☕️ Keurig & standard brewing coffee pot 🧑‍🍳 Fully stocked kitchen ⚡️ High speed inte

5 out of 5 average rating, 205 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

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.

5 out of 5 average rating, 92 reviews

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.

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.

5 out of 5 average rating, 27 reviews

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.

4.92 out of 5 average rating, 118 reviews

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

*POOL OPEN EARLY MAY 1ST* The Oasis Retreat, located right outside downtown South Haven, is perfect for year round adventures & only 4 block walk from downtown. It boasts a heated pool, hot tub, outdoor bar, backyard, 2nd unit, & fire pit. Ideal for families it includes Wi-Fi, kitchen, laundry, patio, outdoor bar, outhouse, & more. Hot tub: Open Year Round Pool & Outdoor Area: Open May-October 1) https://www.airbnb.com/slink/PSGEaadD 2) https://www.airbnb.com/slink/R5t9UwVUk

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.

4.92 out of 5 average rating, 26 reviews

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

4.97 out of 5 average rating, 234 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, 131 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.

4.83 out of 5 average rating, 185 reviews

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

A private swimming pool is surrounded by a spacious patio featuring a hot tub and comfortable seating areas. The home is positioned in the background, with large windows allowing natural light. A white picket fence encircles the area, providing privacy.

4.95 out of 5 average rating, 20 reviews

Private Pool, Hot Tub & Outdoor TV

Escape to a 4-bed, 1.5-bath home with a PRIVATE POOL, HOT-TUB and OUTDOOR TV. So many activities to enjoy. Beaches - Lincoln Township Beach 6.4mi - Silver Beach 8.0mi (TOP 3 beach in Michigan) - Jean Klock 9.6mi - Weko Beach 11mi State Parks - Grand Mere 5.8mi - Warren Dunes 14mi Wineries - Baroda Founders 6.6mi - Round Barn & Estate 8.0mi - Tabor Hill 8.8mi - Hickory Creek 10mi Golf - Blossom Trails 7.9mi - Harbor Shores 8.4mi - Pebblewood 9.9mi

Townhouse in Saint Joseph

An expansive rooftop patio features ample seating with a sectional sofa and individual chairs arranged around a coffee table. The area is filled with natural light, and clear views of the surrounding landscape can be observed under a bright blue sky.

5 out of 5 average rating, 9 reviews

Marina Sunset: Savor Summer Days

Located in the beautiful beach town of Saint Joseph, Michigan, this brand new waterfront townhome is located within Harbor Shores Resort. The area's natural beauty can be seen throughout several dunes areas and beaches nestled on the southeast corner of Lake Michigan. Enjoy wineries, award winning breweries, and an abundance of restaurants. There are adventures abound with boating, fishing, hiking, and biking all nearby.

Townhouse in Saint Joseph

A comfortable living area features a light gray sectional sofa adorned with pink and white accent pillows. A round coffee table rests on a patterned blue area rug, while a large television sits on a decorative media console. Windows allow natural light to illuminate the space.

5 out of 5 average rating, 18 reviews

Family Tides at Harbor Shores

The ultimate family retreat awaits at this 3BR townhouse, boasting captivating marina views. Unwind in comfort with two restful king beds for a good night's sleep after family adventures. Explore charming cafes, exciting water sports, golfing, and Silver Beach. Embark on riverside strolls along the paved walkway, let the kids splash in the inviting heated pool, and stay seamlessly connected with fast Wi-Fi.

Popular amenities for St. Joseph rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 45 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.

An overhead view captures a community pool surrounded by neatly arranged lounge chairs and small tables, with a hot tub located nearby. The landscape includes manicured grass and a stone border, creating an inviting area for relaxation.

4.77 out of 5 average rating, 13 reviews

On The River! Assn Pool, Hot Tub

4.96 out of 5 average rating, 90 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-POOL, Summer 2026 Awaits!

4.96 out of 5 average rating, 189 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

4.94 out of 5 average rating, 174 reviews

A private hot tub is set in a wooden enclosure, surrounded by a serene natural landscape. Steps lead up to the hot tub, offering easy access. Two white Adirondack chairs are positioned nearby, inviting relaxation in the peaceful outdoor setting.

Home in Union Pier

New Hot tub Heated Pool Union Pier

5 out of 5 average rating, 35 reviews

A large heated saltwater pool is set in a manicured grassy area, surrounded by trees. The spacious house features multiple windows, reflecting natural light. Comfortable seating options are visible on a deck beside the pool, inviting relaxation in a private outdoor setting.

Home in Three Oaks

Private! Cherry Beach Pool House

4.9 out of 5 average rating, 50 reviews

A vibrant yellow front door is complemented by stone exterior and a decorative statue. The private pool area features clear blue water, surrounded by loungers on a spacious deck. An indoor sitting area is arranged with green and yellow decor, large windows allow natural light to fill the space.

Home in Michigan City

Cozy Mid-Century Home•Private Pool• Dog-friendly!

4.99 out of 5 average rating, 217 reviews

Home in Vandalia

Quiet Couples' Retreat, Stock Tank Pool, Nature

Condo rentals with a pool

4.92 out of 5 average rating, 177 reviews

A cozy living area displays a striped red sofa and an armchair, complemented by a coffee table with a decorative box. A colorful beach-themed painting hangs on the wall, and the adjoining area features a small kitchenette with white cabinetry.

Condo in Saugatuck

Robyn's Top Notch Nest#7

4.94 out of 5 average rating, 34 reviews

Condo in Saugatuck

Waterfront couples getaway near beach and trails

5 out of 5 average rating, 26 reviews

Condo in South Haven

South Haven North Shore condo

5 out of 5 average rating, 5 reviews

An outdoor pool is surrounded by lounge chairs, providing a relaxing area for guests. The three-story building features balconies on the upper floors. Clear blue skies add to the inviting atmosphere, enhancing the setting for relaxation and leisure.

Condo in New Buffalo

Perfect Location Condo Pools Walk to all Beach 1.5

4.97 out of 5 average rating, 37 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!

5 out of 5 average rating, 12 reviews

An indoor heated pool is enclosed by large glass windows that allow natural light to fill the space. Comfortable lounge chairs are arranged nearby, alongside a pool ladder leading into the clear blue water. The brick walls contribute to a modern and inviting ambiance.

Condo in South Haven

Schoolhouse Suite: Indoor assoc. pool, hot tub!

4.94 out of 5 average rating, 95 reviews

A modern living room features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table sits in front of the sofa, while two lamps provide soft lighting. Artwork adorns the wall above, accompanied by a round mirror reflecting the space.

Condo in New Buffalo

Nightingale Dunes - Modern beach town retreat

4.97 out of 5 average rating, 244 reviews

Condo in Douglas

Fun condo perfect for spring and summer fun.

Other vacation rentals with a pool

4.96 out of 5 average rating, 82 reviews

The exterior of the cottage is presented, showcasing a spacious screened-in porch framed by greenery. The flat roofline and large windows invite natural light, while a neatly landscaped area with a stone border enhances the tranquil setting. Lush grass complements the peaceful environment.

Cottage in Sawyer

Rosie’s Cottage close to Warren Dunes (w pool)

5 out of 5 average rating, 8 reviews

Townhouse in Union Pier

Luxe by the Lake - Pool Access - Walk to Beaches

4.67 out of 5 average rating, 3 reviews

A spacious brick home is set against a backdrop of manicured land, characterized by a large front lawn with neatly maintained grass. Vibrant trees, including a blossoming pink one, add a touch of color to the exterior. A clear blue sky completes the serene scene.

Home in Baroda

Holden Retreat

4.85 out of 5 average rating, 65 reviews

An outdoor gathering area features a fire pit surrounded by seating, inviting conviviality. Nearby, a bubbling hot tub is framed by trees, providing a secluded retreat. Dining tables with chairs offer ample space for outdoor meals, and a foosball table awaits action in the game room.

Home in Coloma

Private Modern Oasis: Fire pit, Hot tub, Sleeps 12

4.94 out of 5 average rating, 85 reviews

An open living space features a cozy leather sofa and a rustic wooden coffee table. Large windows allow natural light to fill the room, complemented by a ceiling fan. A pellet stove is located near the seating area, creating a welcoming environment.

Barn in Benton Harbor

Updated Pool House with Private Pickle Ball Court

Vacation home in Stevensville

An aerial view captures a lakeside community featuring numerous chalet-style homes. Lush greenery surrounds the area, with the shimmering expanse of Lake Michigan visible in the background. A swimming pool and recreational facilities can be seen, along with parking areas and sandy volleyball courts.

4.93 out of 5 average rating, 69 reviews

A-Frame On Lake Michigan - beach, sports, + pool

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 Community

This charming home features a welcoming front porch with white columns and a neatly landscaped yard. A pathway leads to the entry, framed by manicured grass and small shrubs. The house displays a light exterior with blue accents and large front windows that allow ample natural light.