Holiday rentals with a pool in Shorewood-Tower Hills-Harbert

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Shorewood-Tower Hills-Harbert

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

1 of 1 pages1 / 1

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

4.87 out of 5 average rating, 119 reviews

Cabin with POOL in family resort!

Nestled within a gated 67-acre resort and just minutes from the shores of Lake Michigan, this charming cabin offers a peaceful retreat ideal for couples, families, or solo travelers, blending rustic décor with modern comforts. Guests can spend their days exploring nearby nature trails, lounging by the pool, paddling across the lake, or unwinding on the porch. The perfect vacation for exploring nearby orchards and countryside, catching live music or theater, or just slowing down and recharging!

FamilyValueKitchen

Top guest favourite

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

5.0 out of 5 average rating, 39 reviews

Private! Cherry Beach Pool House

Summer : Aug 21-28, Aug 28-Sept 4 available Get away to Harbor County on this private ¾ acre, open concept home two blocks from Cherry Beach with a large PRIVATE heated pool and hot tub! This home has an open floor plan with natural light filling the spacious living areas. Relax in the 3 seasons room or go for a swim in a ‘15x45’ heated saltwater pool, soak in the hot tub, or roast marshmallows by firepit. New - Universal EV charger. Check our other listing - Warren Woods Pool Retreat

LocationFamilyDecor

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

5.0 out of 5 average rating, 107 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.

LocationValueNearby

Top guest favourite

Home in Sawyer

4.96 out of 5 average rating, 100 reviews

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)!

LocationFamilyQuiet

Superhost

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

4.84 out of 5 average rating, 108 reviews

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.

FamilyLocationHiking

Guest favourite

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

4.95 out of 5 average rating, 85 reviews

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

Welcome to Rosie's Cottage! The cottage has three bedrooms with queen beds, two bathrooms, a fully appointed screened in porch, a lovely fenced deck, an outside eating and lounging area, a full additional kitchen, and fire pit (with seating)! During the summer we have a heated pool. (POOL CLOSED FOR SEASON) And don’t forget the kids' playroom, twin daybeds and pull-out couches in the basement for movie nights with the kids. The cottage is walking distance to the beach and Warren Dunes.

FamilyLocationLayout

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.

Apartment in New Buffalo

4.93 out of 5 average rating, 101 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.

FamilyLocationSleep quality

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

4.97 out of 5 average rating, 245 reviews

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!

LocationFamilyHot tub

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

4.97 out of 5 average rating, 134 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. Maximum Guest Count 16.

LocationFamilyPets

Guest favourite

A private cottage is surrounded by lush greenery and features a wooden deck adorned with several blue planters. Steps lead up to the entrance, which is framed by large windows allowing natural light to fill the interior.

Guest house in Valparaiso

4.95 out of 5 average rating, 227 reviews

Private Cottage in Gated Nudist Community

We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is optional . Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area after payment of grounds fees.

LocationFamilyHospitality

Superhost

A heated swimming pool is set within a spacious outdoor area, surrounded by tall trees and greenery. Several poolside loungers are arranged along the perimeter, providing ample seating. The clear blue water reflects sunlight under a bright sky.

Home in Sawyer

4.95 out of 5 average rating, 40 reviews

Heated Pool + Fire Pit | Near Warren Dunes

Welcome to The Sawyer Retreat! Located in beautiful Sawyer, MI. Nestled on a serene wooded lot, this spacious 3 bedroom 3 bath home offers the perfect blend of comfort, style, and outdoor fun. Just 5 minutes from the beach and Warren Dunes State Park, and a short drive to local wineries, breweries and boutiques that make Harbor Country a favorite destination. Please note the pool is open Memorial Day Weekend through last weekend in September, weather permitting.

ValueLocationHospitality

Guest favourite

Home in New Buffalo

4.94 out of 5 average rating, 139 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) .

ValueLocationHot tub