Holiday rentals with a pool in New Buffalo Township

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.

4.96 out of 5 average rating, 107 reviews

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

4.97 out of 5 average rating, 247 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, 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!

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.

5.0 out of 5 average rating, 215 reviews

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

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.

4.9 out of 5 average rating, 100 reviews

New Buffalo Getaway Condo

This sparkling clean three bedroom condo is an ideal Lake Michigan escape for a family or friends. Enjoy lounging by the condo pool or encounter all that New Buffalo has to offer. The locale is one mile from New Buffalo Beach, and is within driving distance of Four Winds Casino and area wineries. Take advantage of walking around charming downtown New Buffalo with boutique shops, fine dining and an upscale Marina. 36 miles from Notre Dame stadium for fun Fall football weekends. License CR24-0036

5.0 out of 5 average rating, 113 reviews

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.

4.96 out of 5 average rating, 102 reviews

Home in Sawyer

Atomic Acres-POOL, Summer 2026 Awaits!

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)!

4.85 out of 5 average rating, 110 reviews

A spacious outdoor area features a hot tub beside a well-maintained pool. Lounge chairs are positioned around the pool, with a covered seating area in the back. A wooden pergola provides shade, while string lights add a touch of ambiance.

Home in Three Oaks

Play @ The Hideaway - hot tub, sauna, gymnasium

Accommodating up to 22 guests, this expansive 5,891 sqft property is set on 22.6 acres, creating a private oasis complete with a pool, hot tub, sauna, and gymnasium. The residence features a Great Room, fireplace, fire pit, and a private trail, making it an ideal setting for relaxation and recreation. With 3 king-size beds, 4 queen-size beds, and 2 bunk beds with trundles, comfortably catering to the needs of large groups. This venue offers enjoyable experiences for guests of all ages.

4.96 out of 5 average rating, 203 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.

4.96 out of 5 average rating, 112 reviews

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.

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.

4.93 out of 5 average rating, 104 reviews

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.

4.97 out of 5 average rating, 100 reviews

An inviting pool area is surrounded by a wooden deck, featuring comfortable seating arrangements and a large red umbrella providing shade. Lush greenery stands tall in the background, complementing the serene atmosphere of the private fenced space.

Home in Lakeside

Lakeside with heated pool & pvt beach access!

LAKESIDE COTTAGE - POOL, HOT TUB & RARE semi-private Lake Michigan access to gorgeous beach shared by just 10 homes, so it’s never crowded! Beach access is a 7-min walk away (no parking). The pool will close Sept 16th, 2027 this year! Charming, sun-filled cottage sleeps 8 (3BR + pull-out). Heated 85 degree pool (May 22–Sept 15), new hot tub, fire pit, gas fireplace, spacious deck, bluestone patio & grill. 10 mins to New Buffalo, Whistle Stop, coffee - just steps away!

4.94 out of 5 average rating, 142 reviews

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) .

Popular amenities for New Buffalo Township rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 109 reviews

Home in Three Oaks

Wabi Sabi Chic at The Flamingo Ranch in Lakeside

4.97 out of 5 average rating, 105 reviews

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.

4.94 out of 5 average rating, 168 reviews

A spacious deck surrounds a hot tub, with comfortable loungers positioned nearby. In the background, lush greenery frames an open field, and a wooden bridge spans a small area, enhancing the natural setting of the property.

Home in Berrien Springs

18-Acre Pond Retreat | Heated Pool & Hot Tub

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.

4.98 out of 5 average rating, 40 reviews

Modern 5-Bedroom New Buffalo Lakeside Escape

5.0 out of 5 average rating, 38 reviews

Lake House Retreat

5.0 out of 5 average rating, 19 reviews

Home in Union Pier

Harbor Country Poolside

5.0 out of 5 average rating, 28 reviews

Walk to Beach & Downtown | Pool Access

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.

4.98 out of 5 average rating, 44 reviews

The Red Oak-home with fireplace, private pool

Condo rentals with a pool

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.

5.0 out of 5 average rating, 7 reviews

Perfect Location Condo Pools Walk to all Beach 1.5

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.

4.84 out of 5 average rating, 32 reviews

(3 Nt Min!) New Buffalo Condo With Association

5.0 out of 5 average rating, 71 reviews

An aerial view captures a cluster of charming chalets arranged in a semi-circle along the shoreline. The surrounding lush greenery and open parking area enhance the setting. Nearby, amenities such as pools and recreational spaces are visible, blending nature with community living.

Condo in Stevensville

Sunset Pointe Chalet #32: Beach + Pool+ Sports

4.98 out of 5 average rating, 52 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!

A 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.

4.91 out of 5 average rating, 22 reviews

Charming New Buffalo Condo: Walk to Lake Michigan!

4.92 out of 5 average rating, 72 reviews

Large 3BR w/ pool and parking - near everything

4.75 out of 5 average rating, 4 reviews

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!

4.7 out of 5 average rating, 10 reviews

A screened-in porch is equipped with a large dining table surrounded by six chairs. Two lanterns are positioned on the table, enhancing the space's functionality. The porch features a blend of natural light and green walls, with a comfortable seating area for relaxation.

Condo in Union Pier

Union Pier Condo With Heated Pool.

Other holiday rentals with a pool

4.91 out of 5 average rating, 132 reviews

A blue cottage is surrounded by tall trees, featuring large windows that provide ample natural light. A spacious deck extends around the front, with steps leading to the entrance. A chimney is visible on the side, adding to the cottage's charm.

Cottage in Sawyer

The Cranny at Michaels Nook

4.97 out of 5 average rating, 34 reviews

A detailed map of New Buffalo highlights the proximity of New Buffalo Beach to various local attractions. Main streets and pathways are marked clearly, with notable landmarks indicated, allowing for easy navigation by guests seeking nearby amenities and activities.

Apartment in New Buffalo

The Beachside Harborfront Hideaway

4.92 out of 5 average rating, 61 reviews

A comfortable living room features a sleek stone fireplace with a mounted television above. Dark leather sofas and a patterned rug create an inviting atmosphere. Natural light filters through two windows, while decorative shelves and a clock add functional charm to the space.

Cottage in New Buffalo

Luxury Cottage with pool; summer will book fast

4.65 out of 5 average rating, 20 reviews

The Whit: Summer Paradise – Hot Tub & Pool

A stylish living room features a modern leather sofa and a square coffee table. A stone fireplace sits beneath a flat-screen TV. A framed wall art displaying greetings in various languages adds an inviting touch, while an acoustic guitar leans against the wall.

4.97 out of 5 average rating, 33 reviews

James Dēne 11: Lake Views and Indoor Pool!

4.92 out of 5 average rating, 13 reviews

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

5.0 out of 5 average rating, 36 reviews

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