Vacation rentals with a pool in Berrien County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Berrien County

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

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Guest favorite

Cottage in New Buffalo

4.95 out of 5 average rating, 39 reviews

Luxury Cottage with pool; summer will book fast

The madrona cottage is the perfect vacation home. You will fall in love with the cottage and the location, New Buffalo is amazing. The home has 4 full bedrooms and 3.5 baths. It will sleep 8 guests easy. Everything you need to enjoy a nice vacation is included in the place. The cottage has been completely rehabbed with all spaces being brand new. It's has a heated pool and is close to the beach. Relax by the fire or enjoy the game room with a pool table, card table and games. Great for families.

Guest favorite

Home in Sawyer

4.96 out of 5 average rating, 73 reviews

Fabulous designer owned home w/ heated pool & spa!

Fabulous designer owned home with heated pool & spa in the heart of Sawyer--the ultimate Harbor Country getaway. Renovation has been recently completed at this amazing 5 bedrooms, 5 bath home w/ heated pool and year-round spa. Wonderful, spacious residence with multiple living areas, two fireplaces, & fully stocked dream kitchen. Secondary family room in lower level. Newly landscaped yard designed w/ privacy in mind w/ fire pit, dining folly, and fully fenced yard w/multi-level deck. Perfection!

Guest favorite

Cottage in Union Pier

5 out of 5 average rating, 29 reviews

Heated pool & private hot tub!

Modern 5 bedroom 3.5 bath home with private hot tub is perfect for large groups, families, couples getaways, and corporate retreats. Soaring ceilings open concept space provides plenty of room for gathering. Access to association heated pool (open late May thru Columbus Day) and clubhouse. Short walk to Townline Beach, farmers market and all that Union Pier has to offer. Enjoy the fire pit for s’mores and the private hot tub out back making this the perfect home for vacationing in all seasons.

Superhost

Home in Three Oaks

4.8 out of 5 average rating, 5 reviews

Gray Haven: Stunning Woodland Retreat w/ Pool

Set on a tranquil 1.25-acre wooded lot less than two miles from Townline Beach, this luxurious home is a vacay dream! The open design LR-DR-Kitchen, high ceilings, majestic stone fireplace and fabulous natural light draw you in. Then the elegant, comfy furnishings and stylish decor, plus a way-cool pool, huge deck and screened gazebo invite you to R-and-R to the max. Gather around the large kitchen's center island or b'fast nook for coffee. Relax by the outdoor fireplace and count stars. Boom.

Guest favorite

Home in Three Oaks

5 out of 5 average rating, 33 reviews

Private! Cherry Beach Pool House

2025 Summer Calendar Open! 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 NEW listing - Warren Woods Pool Retreat!

Guest favorite

Home in St. Joseph

4.96 out of 5 average rating, 24 reviews

Poolside Oasis - Private Heated Pool + Fun Games

Escape to our stunning 4-bed, 1.5-bath home with a private in-ground pool! Bright living spaces, a fully equipped kitchen, cozy bedrooms, and an amazing pool await. Conveniently located near charming Saint Joseph, Michigan, with Lake Michigan's sandy shores and vibrant downtown nearby. Indulge in local cuisine, explore nature trails, then return to the comfort of our inviting home. Your ultimate vacation experience awaits! Book now for an unforgettable getaway!

Guest favorite

Cottage in Union Pier

4.96 out of 5 average rating, 192 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, pool, 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 and create lasting memories!

Guest favorite

Cottage in New Buffalo

4.96 out of 5 average rating, 102 reviews

Casa Playa New House w/ Private Spa & Pool Access

This 4 bedroom getaway is located in the heart of Harbor Country and is just a 10 minute walk or 3 minute drive to the best beach in Union Pier! Casa Playa has EVERYTHING a vacation house can offer: an association POOL, a private HOT TUB, high speed internet that accommodates many people working from home, a cozy indoor fireplace, an outdoor fire pit, an outdoor deck & grill, 2 smart Tvs, ALL brand new appliances, and games for the whole family!

Guest favorite

Home in Lakeside

4.96 out of 5 average rating, 71 reviews

Charming Lakeside -hot tub, pool, pvt beach access

Pool closed for 2024 season! CHARMING COTTAGE W/ MODERN UPDATES IN HARBOR COUNTRY WITH HOT TUB, FIREPIT & PRIVATE BEACH ACCESS TO LAKE MICHIGAN IS A 7 MIN WALK AWAY! SUN-FILLED & FULL OF CHARM, YOU WILL FEEL RIGHT AT HOME THE SECOND YOU WALK IN. SLEEPS 8 GUESTS (3 BEDROOMS & PULL-OUT COUCH) AND COMES WITH A GAS FP, GREAT KITCHEN WITH DIRECT ACCESS TO DECK, BLUESTONE PATIO & GRILL. THE LOCATION COULDN'T BE BETTER!!

Superhost

Home in Bridgman

5 out of 5 average rating, 4 reviews

The Poolside Escape | Hot Tub | Arcade | Ping Pong

Discover The Poolside Escape Discover a beautifully renovated single-story ranch with a finished basement, just minutes from Southwest Michigan’s best beaches, state parks, and wineries. Perfect for families or friends, The Poolside Escape offers modern amenities, including a private pool, hot tub, and entertainment options, to make your getaway truly unforgettable. Pool open Memorial Day to September 15th

Guest favorite

Home in Sawyer

5 out of 5 average rating, 23 reviews

The Summer House - Heated Pool - Steps to Sawyer

Welcome to the Summer House! Our newly renovated private home featuring a heated pool is located steps to downtown Sawyer; just a 3 minute drive to Warren Dunes State Park. Enjoy all Harbor Country has to offer while staying in your own home walking distance to coffee, restaurants, and shops! Guest will have access to a private gated pool and parking right in front of the house for four vehicles.

Superhost

Home in New Buffalo

4.75 out of 5 average rating, 4 reviews

New Buffalo Pool/Hot-tub/Firepit

Your family will be close to everything when you stay at this centrally-located place. This five bedroom 3 bath home has it all including pool, hot-tub, firepit, fenced yard. Steps from a the association beach (small beach currently) walking distance to the large public beach, town, and marina. Renovated in 2023.