Holiday rentals with a pool in Van Buren County

Harbor Escape

Welcome to Harbor Escape - a stylish and fun townhouse in the Harbor Club resort community of South Haven. Newly listed, we have designed this home to make your vacation memorable with amenities for the whole family. As a guest, you’ll have access to the private marina, clubhouse, heated seasonal pool and an indoor/outdoor year-round pool. This is a perfect South Haven hub - just a walk 5 minutes to Newcome Beach, short drive to South Beach or drive a few minutes to explore the vibrant downtown!

Northern Anchor: Beachy Game Room - Pool & Hot Tub

The new enclosed subdivision pool & hot tub are now open! Enjoy our beautiful vacation house. Fully furnished with loads of thoughtful details. Perfect for families with kids or for groups/individuals looking for a relaxing get away. Close to everything: beaches, downtown shopping, wonderful restaurants, award winning golf courses, pick your own orchards, beautiful wineries and much more. Visit us year round - from snowy woods to sandy beaches - the Northern Anchor has something for everyone.

Riverside Home Near Beaches, Pier, downtown

Welcome to The Harbor Hideout in St. Joseph, Michigan! Dockside, Modern riverfront retreat minutes to Lake Michigan Beaches, Piers, downtown shops, carousel and more. Sleeps 10 with 4 sleeping areas, 4 baths, and TVs in every room. Enjoy the basement game room with pool table and PlayStation, community pool & jacuzzi (open after Memorial Day), and updated modern furnishings. Perfect area for boating, relaxing, and summer fun. Open-concept living, grill, and firepit. Your ideal summer getaway!

Amazing Beach Condo with pool and great sunsets!

Unwind with your family at this peaceful getaway! This cozy retreat features 1 bedroom, 1.5 bathrooms, and a pull-out couch in the living room. Enjoy exclusive access to a private beach and a community pool reserved for the condo association. Relax on your private deck while taking in breathtaking sunsets, just a short 5-minute walk from the beach! Located between South Haven and St. Joseph, Michigan, this charming spot offers easy access to local wineries, nature centers, parks, and more!

Harbor Shores House with Bunk Beds and Pool!

Escape to a tranquil retreat in this 3 bedroom cottage in Harbor Village, where comfort and convenience await. You'll love being situated in the Harbor Shores neighborhood, where downtown St. Joseph and Benton Harbor’s quaint shops and restaurants are just a short walk or bike ride away. The home enjoys stunning views of the marina and golf course from the front porch and terrace accessible via the master suite. Swim and/ or relax at the pool located steps away - right across the street.

Downtown Loft: Indoor Pool, Hot Tub, Gym, Theater

Central Lofts condos used to be the old Central High School. We are located in downtown South Haven. Stay 2 blocks from the Farmer’s Market, also an ice skating rink in winter. The building has a shared indoor pool and hot tub, 2 old fashioned private movie theaters (seats 12) and an exercise room. This cute condo has a king bed and twin sized trundle bed in master bedroom, and two pullout couches in living room. Walk to town & the beach, .7 miles to S. Beach and 2 blocks to town. Very chic!

Hagar Beach House

Clean and Fresh 4- bed home Central AC , 5 min walk to our favorite Lake Michigan beach at Hagar park. Large Pool deck and pool. Beautiful old beech trees with multiple hammocks in tree stand . Full basement with kitchenette and full bath with divider separated queen bed sleep area. There’s an extra pullout sleeper couch downstairs . Large dining table seats up to 12. After your beach time relax on poolside deck , nap in the handful of hammocks clustered within the amazingly Tall Beech tree

The Oasis Retreat

The Oasis Retreat, located right outside downtown South Haven, is perfect for year round adventures & only 4 block walk from downtown. It boasts a heated pool, hot tub, outdoor bar, backyard, 2nd unit, & fire pit. Ideal for families it includes Wi-Fi, kitchen, laundry, patio, outdoor bar, outhouse, & more. Hot tub: Open Year Round Pool: Mid-May to Mid-October If unavailable, consider our nearby properties: 1) https://www.airbnb.com/slink/PSGEaadD 2) https://www.airbnb.com/slink/R5t9UwVUk

Updated Pool House with Private Pickle Ball Court

Ideal for families this is the perfect escape from city life. Our repurposed barn is a unique "Glamping" adventure, wake up to the crow of our roosters and enjoy fresh eggs every day. Just outside of St Joe & Benton Harbor, enjoy your stay in this repurposed old hatchery with exclusive use of the in-ground pool. Take advantage of the 30 acres surrounded by a creek & river or make us your home base for exploring the wineries, golf courses, hiking trails & beaches in the surrounding area.

Driftwood Shores- Spring is Coming!

Summer is booking fast! June 8 to 11 and most of August after the 14th are still open. Enjoy a trip to beautiful South Haven along the shores of Lake Michigan. Driftwood Shores is a charming 1,680 sq. ft. home in the Harbor Club Resort. It has everything you need to enjoy a peaceful family vacation, friends getaway, or girls weekend out. The Resorts Indoor/Outdoor Pool with retractable roof and outdoor hot tub is open year around from 7 AM to 10 PM. It is included with your stay.

Relaxing Lake Michigan Getaway, great location!

FALL/WINTER SPECIAL! Enjoy a relaxing getaway on Lake Michigan. Now offering long term rentals for the off season. Close to everything, but away from it all. Beautiful bluff views of Lake Michigan. Enjoy access to a private beach and a pool. Close to downtown St. Joe. and South Haven for fantastic shopping,dining and more! Whether it’s a trip to Saugatuck Dunes State Park, enjoying one of the many area wineries or just lounging on the beach, there’s something for every

SunKissed Sanctuary + Pool + Hot Tub +CentralLofts

A stylish, historic lower-level loft featuring exposed brick and ductwork paired with true floor-to-ceiling walls for much-needed privacy. Designed by a family for families, this South Haven retreat blends charm, comfort, and convenience in a walkable location close to South Haven's countless activities. Amenities at Central Lofts include year-round access to a pool and hot tub, a fitness room, and seasonal access to a spacious shared patio with three grills.