Holiday rentals with a pool in Michigan

4.85 out of 5 average rating, 109 reviews

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!

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!

4.97 out of 5 average rating, 102 reviews

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

A newly constructed beach house features a spacious front porch with multiple seating areas, surrounded by a white picket fence. Large double doors lead into the home, while light-colored siding complements the nearby colorful residences.

4.99 out of 5 average rating, 83 reviews

6BR Beachwalk Gem |Beach+Pool & Lake Michigan View

Beach Plus Resort Amenities! Perfect for families—close to events, water, and summer fun. Located within the Beach Walk this space offers stunning Lake Michigan views, easy across the street access to the beach, 6 bedrooms, 5 baths, 2 living spaces. This comfortable and relaxing beach setting will sleep up to 18 adults. We have 3 large decks, grill and outdoor seating. Plus Enjoy access to community pool, pickle ball, paddle boards, coffee/ice cream shop kayaks, playground and other fun rec!

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.

4.9 out of 5 average rating, 50 reviews

Cozy~Well-Curated Home•Private Pool• Dog-friendly!

Welcome to The Keystone Ranch! Vintage charm meets modern comfort in our bright & airy, limestone ranch home. It’s a perfect getaway for families or friends…just minutes away from our beautiful beaches & outdoor adventures. We’re located in the ❤️ of Michigan City, close to great food & SO MANY local favorites! What You’ll love… •in ground pool + fenced in yard •3 season lanai + fire pit •Spacious kitchen •Lower level chill space Perfect central location… close to INDIANA DUNES NATIONAL PARK!

5 out of 5 average rating, 208 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

4.97 out of 5 average rating, 119 reviews

An outdoor seating area features a cushioned sectional sofa and a wooden coffee table, overlooking a heated in-ground pool. Lounge chairs are positioned nearby, surrounded by trees, with a view of Lake Michigan in the background.

Guest suite in Gary

Beachfront- Lake Michigan-Hot Tub-Heated Pool

Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

A charming two-story cottage is showcased, featuring multiple large windows that allow abundant natural light. The exterior is accented by a mix of dark brown and light beige siding, with a wooden door leading into the home. Lush greenery surrounds the property.

5 out of 5 average rating, 13 reviews

Hilltop Cove- Beautiful 2 bed/ 2 bath in Beachwalk

Welcome to Hilltop Cove! Your perfect getaway at our stunning 2-bedroom, 2 full bathroom cottage in the desirable Beachwalk resort community. Nestled just a short walk or golf cart ride away from the incredible amenities this vibrant community has to offer such as a pool, lake and park. Our property promises a relaxing and fun-filled stay for all guests. Book your stay at our Beachwalk spot and experience the ultimate in comfort, convenience, and coastal charm. We look forward to hosting you!

A screened-in porch features comfortable seating facing the tranquil waters of Lake Kai. Large windows provide an unobstructed view of the serene sunset reflecting on the lake, creating a peaceful and inviting space.

4.85 out of 5 average rating, 91 reviews

Beachwalk Home on Lake Kia - W/ Cart Rental Option

Our Lakehouse is unique in that it's sits directly on Lake Kai - Beachwalk's beautiful interior Lake. Of the 200+ homes located in "Beach Walk" Resort, less than 20 are on Lake Kai making our home very unique & your vacation memorable. It’s definitely one of the most sought out locations in all of Beachwalk ** Exciting NEW Update for the 2026 Season New Golf Cart Rental Option - reserve after booking ** Minimum 30 years of age to book ** ** Maximum capacity is 8 Adults and 8 Children **

Guest house in Valparaiso

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.

4.95 out of 5 average rating, 218 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.

Guest house in Michigan City

The exterior of Lagunitas Coach House is shown, featuring a screened-in porch with two red chairs. Lush greenery and flowers surround the entrance, while a small table rests beside the chairs. A clear blue sky provides a bright backdrop.

4.86 out of 5 average rating, 167 reviews

Lagunitas Coach House in Beachwalk, Lake Michigan

Lagunitas Coach House is a sought after location on the quaint Thomas blvd cul de sac. It is the coach house to Gooch Life. It is the perfect get away spot for a couple or small family wanting to escape to the beautiful beach of Lake Michigan. Lagunitas and Gooch Life share the property but are separate structures. Lagunitas has a private entrance, amenities, and parking. Lagunitas sleeps 6, see pictures for bed configuartion.

4.93 out of 5 average rating, 130 reviews

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 9/20 and hot tub. 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 2 new homes on 3 acre property, this home and 1 guest home ( rented separately) .

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.