Private Pool Vacation Rentals
Our vacation rentals with their own private pool offer guests the perfect opportunity to indulge without ever leaving the backyard of their own home-away-from-home. Meticulously maintained and regularly sought after, don’t wait, our collection of private pool homes books fast.
Need more pool options? Search additional Southwest Michigan vacation rentals with pools, including shared community pool access.
19 properties available
Truly fabulous, Bear Ranch sets you up for an amazing opulent vacation! In this huge estate home featuring 3 floors of elegance-meets-R-and-R, cathedral ceilings and abundant natural light, you and your guests can enjoy relaxing in front of a stone fireplace or spending time in a huge, fully-equipped game room, bar area or movie room. The Chef's Ki
Bear Ranch
House
Berrien Springs, MI
8
bedrooms
6
baths
1
half baths
32
guests
5
(23)
Welcome to Casa Azur, your ideal vacation retreat in the sought-after Gowdy Shores neighborhood of Union Pier just minutes to popular SW Michigan attractions! This exceptional 5-BD/3-BA residence offers an array of luxuries, including a private pool, hot tub, sun porch, and outdoor shower. Nestled within walking distance of the neighborhood's prist
Casa Azur
House
Union Pier, MI
5
bedrooms
3
baths
10
guests
5
(2)
Perched on the shores of Lake Michigan, this rare 6-BR, 5-BT lakefront gem offers luxury, charm, and breathtaking views. A retreat for relaxation and entertainment, it features expansive decks, a sparkling pool, and a cozy firepit for sunset gatherings. The bright, elegant interiors blend comfort with style, while the basement game area adds fun fo
Lake Shore Living
House
Michiana, MI
6
bedrooms
5
baths
16
guests
Welcome to Aqua Breeze-sitting on 3 wooded lots just a short walk to a white crystal sand beach-a true Vacay Paradise! Featuring a huge, heated pool, fabulous deck, screened porch and 3 fireplaces, you'll enjoy maximum R-and-R, plus kids love the great yard and plenty of games! Life is good with a Primary BR with Jacuzzi and private balcony, 2 BRs
Aqua Breeze
House
Union Pier, MI
3
bedrooms
2
baths
8
guests
A true vacay dream, this stunning lakefront 26-acre estate has a private beach, a gorgeous pool, hot tub, indoor sauna, a fabulous 6-bedroom home and so much more! The lush, spacious open design gives you options galore for enjoying maximum R-and-R. Living room and family room fireplaces and flat-screen TVs provide chill-time while the Chef's Kitch
Dunegrass Path
House
Stevensville, MI
7
bedrooms
6
baths
16
guests
5
(9)
Mile-wide Lake Michigan views and a great open floor plan make this 5BR/4BA lakefront home a vacation dream come true. A heated pool, hot tub, fire pit, balconies, decks and most rooms in the house all feature lakefront vistas that can’t be beat. Spend mornings, afternoons, and evenings outdoors on the deck enjoying the fresh air and sounds of wave
Coastal Escape
House
New Buffalo, MI
5
bedrooms
4
baths
1
half baths
12
guests
4.9
(99)
Presenting The Townie Cottages Collection, newly built, adorable custom cottages that epitomize lakeside luxury, designed exclusively by Kate Marker Interiors (whose work has been recognized by Architectural Digest and Luxe Home). Nestled in the heart of Union Pier, these 4 exquisite cottages offer a blend of rustic charm and modern elegance, ensur
The Townie Cottages - All Units
Multi-Unit
Union Pier, MI
7
bedrooms
5
baths
1
half baths
22
guests
This spacious, captivating 6BR/3.5BA home in a golf-cart friendly area has a huge back yard and pool, hardwood floors and a 2-story great room, plus a stone fireplace flanked by huge windows! The gourmet kitchen has a granite-top island and hi-end appliances. The upper-level Master suite features a gas fireplace and private balcony with Lake Michig
Main Destination
House
Grand Beach, MI
6
bedrooms
3
baths
1
half baths
12
guests
5
(57)
Exquisite 4BR-2.5BA vacation home on 1½ wooded acres, less than a mile from Lake MI beaches! Cathedral ceilings, Great Room, stone fireplace, hardwood floors and deluxe furnishings. Chef's kitchen has granite island, hi-end appliances. Large plush enclosed porch w/ dining table, great views! Huge yard, pool, hot tub, patio, grill, outdoor full BA.
The Dakota
House
Union Pier, MI
4
bedrooms
2
baths
1
half baths
9
guests
5
(96)
Welcome to Bella and Dulce's Lakehouse! This freshly remodeled retreat offers the perfect blend of modern luxury and natural beauty. Enjoy the serenity of a private wooded lot while taking a dip in the refreshing pool or roasting marshmallows by the firepit. Inside, the designer kitchen is a chef's dream, and the 4 BDs and 3 full BAs ensure comfort
Bella and Dulce's Lakehouse
House
Union Pier, MI
4
bedrooms
3
baths
10
guests
5
(13)
A mixture of modern design, an inviting color palette, and curated furnishings create a sophisticated Harbor Country enclave that will impress even the most seasoned traveler. Owlwood boasts 4 ensuite bedrooms, open social areas, high-end appliances, and indoor/outdoor living brilliantly built around a large private courtyard. Pet friendly w/ a ni
Owlwood
House
Harbert, MI
4
bedrooms
4
baths
9
guests
5
(17)
Gorgeous "cabin" on 15 acres of Indiana farmland loaded with amenities: pool, spa, deck, fishing pond, pastures, barn. Spacious, luxurious interior: stainless-steel appliances, custom stonework, fireplace, huge windows. 5 BR, one is main ensuite - priv. bath and deck; 2 more full baths, all lushly styled. Sleeper sofa, Wii-TV, Bluetooth speakers, g
Scout's Haven
House
Rolling Prairie, IN
5
bedrooms
3
baths
12
guests
4.9
(21)