Holiday rentals with a pool in Michigan

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.

4.91 out of 5 average rating, 56 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, 31 reviews

The charming exterior of a light purple house features a welcoming porch with steps leading up. Large windows allow plenty of natural light, while a white picket fence surrounds the property, enhancing its inviting appeal.

Home in Long Beach

Beachwalk- New Kids on the Beach

This Beachwalk favorite has all "The Right Stuff" for your next getaway. Reconnect with family and friends by Lake Michigan at New Kids on the Beach. Awesome 2nd floor large room with 6 built in twin beds and large TV. Amenites include a Hot Tub to relax under the stars and a Golf cart to help load beach gear or ride to the Beach Hut for ice cream. This home has some of the best outdoor space with firepit, screen porch, deck, hot tub, and outdoor shower. Close to wineries, casino, zoo, dunes

4.97 out of 5 average rating, 125 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 Miller

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, 14 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, 94 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 **

4.99 out of 5 average rating, 90 reviews

6BR BeachWalk Gem | Beach+Pool+Lake Michigan View

Beach + Resort Amenities! Perfect for families—close to events, water, and summer + fall fun. Located in BeachWalk Community this space offers stunning Lake Michigan views, easy across the street access to the beach, 6 bedrooms, 5 baths, 2 living spaces. This comfortable + relaxing beach setting will sleep up to 18 adults. 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!

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.

4.96 out of 5 average rating, 199 reviews

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.

The exterior of a two-story red house is showcased, featuring a welcoming porch with railings. Large windows allow natural light to fill the home, and a paved pathway leads up to the entrance. Surrounding trees enhance the setting's natural charm.

4.99 out of 5 average rating, 86 reviews

Beachwalk Resort Stunning 4-Bed + Loft - Sleeps 18

NOTE: I CAN OFFER EARLY CHECK-IN/LATE CHECK-OUT OFF SEASON SUBJECT TO AVAILABILITY. Stunning newer home featuring beautiful open floor plan with amenities for the whole family. Exceptional property in the award winning Beachwalk Resort. When not at the beach, you can comfortably sit back and enjoy a cup of tea in the screened in porch or a glass of wine around the firepit while the kids compete in a friendly game of air hockey. Come on in and let your vacation dreams come true.

4.97 out of 5 average rating, 244 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!

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, 225 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.

4.93 out of 5 average rating, 138 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 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) .