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Vacation rentals with a pool in Grand Beach

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Grand Beach

  • Total vacation rentals

    Explore 40 vacation rentals in Grand Beach

  • Nightly prices starting at

    Grand Beach vacation rentals start at $637 CAD per night before taxes and fees

  • Verified guest reviews

    Over 480 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Grand Beach vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Grand Beach rentals

  • 4.8 Average rating

    Grand Beach stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Grand Beach

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

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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, 250 reviews
Top guest favourite
A charming cottage exterior is shown with large windows allowing ample natural light. Lush landscaping surrounds the entrance, featuring ornamental grasses and rocky accents. The inviting covered porch provides a welcoming entry point to the home.
Home in New Buffalo

Modern Farmhouse - Walk to Downtown, beach & pool!

Newer construction and beautifully decorated w/ Magnolia Farms vibe! Just 2.5 blocks from downtown New Buffalo, 10 min walk to the beach, nearly 2,700 sq ft, situated at the end of a private lane. 4 BR and 3.5 baths on 3 floors with 2 separate living areas, a screened-in patio & covered front porch. Pool table, 2 large TVs w/streaming in separate living areas. Heated community pool for residents & guests, bikes, gas grill and much more! Note: Reservation Agreement to be signed post-booking

4.96 out of 5 average rating, 108 reviews
Top guest favourite
A two-story house features a vibrant blue exterior with a spacious porch equipped with rocking chairs. A golf cart is parked in the foreground next to a white picket fence. Clear skies and sunlight enhance the inviting and serene atmosphere.
Home in Michigan City

Beach Nest, Sleeps 20, 5 min. to Lake Michigan.

Beach Nest is a place to relax!! Minutes away from beautiful Lake Michigan. About 1 Hr. away from Chicago Midway and O'Hare airports and Downtown and going east... Notre Dame Football Stadium. Amenities incl. Outdoor Pool, Tennis, Basketball Courts, Putting Green. Paddleboards and Kayaks on Lake Kai. Indiana Dunes National Park, Michigan City Zoo are 10 Minutes away as well as Blue Chip Casino. Horseback riding, Skydiving, Great eateries, Art Galleries. Come and have fun with Family and Friends!

4.97 out of 5 average rating, 106 reviews
Top guest favourite
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

5.0 out of 5 average rating, 219 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, 117 reviews
Guest favourite
Home in Sawyer

Atomic Acres- Pool, Hot tub, Fire pit & more

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, 103 reviews
Top guest favourite
A charming ranch-style house is situated on a spacious green lawn, surrounded by mature trees. The front features a welcoming porch with seating, and a driveway leads to an attached garage on the right. Lush landscaping enhances the tranquil setting.
Home in Bridgman

Cozy Ranch | Huge Fenced Yard| Fall Fun

Escape to a peaceful area of SW Michigan, while being close to everything. Minutes from Warren Dunes and Weko beach, this 3 bedroom ranch home is the perfect fall getaway. Outside, enjoy a large fenced yard, with picnic table, fire pit, lounge chairs, and plenty of space to spend time together. Behind the property, two acres of woods offer a quiet backdrop and a beautiful place to experience the colors of fall. Located near lots of dining, breweries, wineries, orchards, and local farms.

4.98 out of 5 average rating, 100 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, 206 reviews
Guest favourite
Home in New Buffalo

NB Getaway with HotTub, Pool & 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, 113 reviews
Guest favourite
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

Spacious beach condo with crisp white shiplap and midcentury modern style. Great beaches nearby and a heated pool (open Memorial Day to Labor Day) just steps from your door! Perfect for families or groups. Well-stocked kitchen, gas grill, free cable or log into your own apps. Smart TVs in both LRs and all bedrooms. Upstairs loft doubles as a 3rd bedroom. Bonus office! Easy walk or drive to shops, dining & the marina in our quaint beach town. New Buffalo rental permit #26-001.

4.93 out of 5 average rating, 105 reviews
Guest favourite
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.

4.97 out of 5 average rating, 139 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, 143 reviews

Popular amenities for Grand Beach rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
Home in Three Oaks

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

4.99 out of 5 average rating, 112 reviews
Guest favourite
A sparkling saltwater pool is surrounded by a spacious wooden deck, featuring lounge chairs and a shaded seating area beneath a roof. Lush green trees and vibrant landscaping provide a natural backdrop, while a fire pit is visible nearby, creating a relaxing outdoor retreat.
Home in Niles

Bibi's Retreat- Grand 7 Bedroom Private Escape

4.92 out of 5 average rating, 119 reviews
Guest favourite
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 in Beachwalk/Notre Dame weekends

4.93 out of 5 average rating, 122 reviews
Superhost
Home in Grand Beach

Grand Beach & Indoor Pool Retreat

4.71 out of 5 average rating, 7 reviews
Guest favourite
Home in New Buffalo

Pool + Fire Pit | Steps to Beach

4.91 out of 5 average rating, 34 reviews
Guest favourite
Home in Union Pier

Harbor Country Poolside

5.0 out of 5 average rating, 21 reviews
Top guest favourite
A private pool area features a sparkling blue pool with a shallow entry and a floating pool lounge. Six lounge chairs are positioned under large umbrellas on a sun-soaked patio, offering shaded spaces for relaxation. The surrounding green trees provide a serene backdrop.
Home in Three Oaks

Updated Lakeside | Pool (Open!) + Hot Tub + Porch

5.0 out of 5 average rating, 39 reviews
Superhost
Home in New Buffalo

Massive New Home w/Community Pool, Game Room

4.91 out of 5 average rating, 11 reviews

Condo rentals with a pool

Superhost
A dining area features a wooden table surrounded by six chairs, creating a space for gathering. A spiral staircase leads to an upper level, while nautical-themed decor adorns the walls. An adjacent open doorway reveals additional kitchen space, enhancing the home's inviting layout.
Condo in New Buffalo

New Buffalo Getaway Condo

4.9 out of 5 average rating, 101 reviews
Guest favourite
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

5.0 out of 5 average rating, 7 reviews
Guest favourite
A spacious sun deck is presented, featuring several lounge chairs and a table under a red umbrella. The deck is surrounded by a wooden railing, with an expansive view of the nearby harbor and distant buildings.
Condo in New Buffalo

(3 Nt Min!) New Buffalo Condo With Association

4.85 out of 5 average rating, 33 reviews
Top guest favourite
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!

4.98 out of 5 average rating, 57 reviewsA spacious living area is brightened by natural light from large windows. A cozy seating arrangement features striped sofas around a coffee table, with a fireplace nearby. The open layout provides a view towards the kitchen and dining area, enhancing the communal feel of the space.
Condo in New Buffalo

Charming New Buffalo Condo: Walk to Lake Michigan!

4.91 out of 5 average rating, 22 reviews
Condo in New Buffalo

Large 3BR w/ pool and parking - near everything

4.92 out of 5 average rating, 72 reviews
Superhost
A covered patio area features two chairs overlooking a marina with docked boats. Hanging ferns provide greenery, while a table adorned with a floral arrangement and a blue tablecloth adds a pop of color. The sky is partly cloudy with hints of blue.
Condo in New Buffalo

New Buffalo Condo with Association Pool and Beach!

4.57 out of 5 average rating, 7 reviews
Superhost
A shared heated pool is featured in an outdoor area, surrounded by lounge chairs and greenery. A covered patio with seating is visible in the background, along with trees providing shade. Umbrellas offer additional sun protection over certain seating areas.
Condo in Union Pier

Union Pier Condo Close To Everything!

4.75 out of 5 average rating, 4 reviews

Other vacation rentals with a pool

Guest favourite
A large screened front porch is furnished with several wooden rocking chairs and a wicker seating area. Natural light filters through the screens, showcasing the surrounding greenery. A small table sits centrally, creating an inviting space for relaxation and conversation.
Cabin in Three Oaks

Cabin with POOL in family resort!

4.85 out of 5 average rating, 125 reviews
Guest favourite
The multi-story townhome features a light exterior with spacious balconies on each level. Large windows illuminate the structure, enhancing its architectural details. Staircases lead up to the front entrance, inviting guests into the living space.
Townhouse in New Buffalo

Dunescape Beach Retreat, Downtown New Buffalo

4.93 out of 5 average rating, 117 reviews
Superhost
A sunlit living area features large windows that allow ample natural light, showcasing a cozy gray sofa and a round white coffee table on a woven rug. A wall-mounted TV and a small blue armchair enhance the space, while wooden paneling adds warmth.
Apartment in New Buffalo

Woodsy Lake Michigan Getaway: 3-BR, 2-BA

4.92 out of 5 average rating, 13 reviews
Superhost
A spacious patio area is visible, featuring a circular in-ground pool surrounded by a sunlit deck. Several white lounge chairs are positioned nearby, along with an umbrella-topped table. A two-story white cottage stands in the background, with large windows allowing natural light to enter.
Cottage in Grand Beach

Cottage steps from Lake Michigan

4.68 out of 5 average rating, 22 reviews
Top guest favourite
A charming house is showcased with a striking orange exterior. The covered front porch features white railings and a decorative ceiling. A well-maintained walkway leads to the entrance, bordered by colorful foliage. Nearby homes are visible, set in a peaceful neighborhood with a wooded backdrop.
Home in New Buffalo

Modern 5-Bedroom New Buffalo Lakeside Escape

4.98 out of 5 average rating, 43 reviews
Top guest favourite
A private heated pool is surrounded by a stone patio, offering lounge chairs for relaxation. A spacious deck sits behind the pool, providing access to a well-maintained house. Lush greenery frames the scene, enhancing the tranquil atmosphere for outdoor enjoyment.
Home in New Buffalo

The Red Oak-home with fireplace, private pool

4.98 out of 5 average rating, 45 reviews
Superhost
Home in Union Pier

Pool & Spa • 5K SqFt Schoolhouse • 2 Game Rooms

4.73 out of 5 average rating, 62 reviews
Guest favourite
The exterior of a modern home is framed by tall trees. A welcoming front porch features yellow chairs and an American flag. The stone pathway leads to a manicured lawn, providing an inviting approach to the entrance. A garage door is visible on the right.
Cottage in Union Pier

Heated Pool & Pvt Hot Tub

5.0 out of 5 average rating, 50 reviews

Destinations to explore