South Side holiday rentals
We found 438 holiday rentals — enter your dates for availability
Discover a selection of 117 homes and other holiday rentals in South Side that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll have the amenities that you expect and more, which might include parking and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts – South Side
Showing deals for:13 Nov - 20 Nov
Exceptional
(82 reviews)
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
South Haven
S$3,691
for 7 nights, 1 home
S$527 per night
includes taxes & fees
Exceptional
(32 reviews)
Casa de Sarno. Short Walk to Lake Michigan Beach. Dog Friendly.
South Haven
S$7,773
for 7 nights, 1 home
S$1,110 per night
includes taxes & fees
Exceptional
(46 reviews)
Prime location! Dog friendly; close to beach, restaurants, shops! New kitchen!
South Haven
S$4,079
for 7 nights, 1 home
S$583 per night
includes taxes & fees
Exceptional
(188 reviews)
1-bedroom cottage steps to Lake Michigan Beach fire pit
South Haven
S$2,740
for 7 nights, 1 cottage
S$391 per night
includes taxes & fees
Exceptional
(67 reviews)
AVERY STREET BEACH HOUSE. SLEEPS TWELVE! SIX BEDROOMS! FOUR BATHS!
South Haven
S$14,001
for 7 nights, 1 home
S$2,000 per night
includes taxes & fees
Exceptional
(97 reviews)
Walk to Beach & Downtown • River + Lake Views • Huge 3-Level Home Sleeps 16
South Haven
S$4,699
for 7 nights, 1 home
S$671 per night
includes taxes & fees
Exceptional
(18 reviews)
Beach Front, Pool, Short walk to Downtown. Look No more! Peaceful Paradise
South Haven
S$3,254
for 7 nights, 1 apartment
S$465 per night
includes taxes & fees
Exceptional
(39 reviews)
THE OAKLAND NORTH! ACCOMMODATES TEN GUESTS! 4 BDRMS/3 BATHS! NORTH BEACH!
South Haven
S$5,636
for 7 nights, 1 home
S$805 per night
includes taxes & fees
Exceptional
(106 reviews)
INDIANA AVENUE BEACH HOUSE 5 BDRMS. 4 BATHS. ACCOMMODATES TWELVE GUESTS!
South Haven
S$5,198
for 7 nights, 1 home
S$743 per night
includes taxes & fees
Exceptional
(63 reviews)
Fun inside or out with game room, fenced yard and 1/2 mile to beach or town.
South Haven
S$2,325
for 7 nights, 1 home
S$332 per night
includes taxes & fees
Exceptional
(106 reviews)
2 blocks from Lake Michigan family friendly
South Haven
S$2,578
for 7 nights, 1 apartment
S$368 per night
includes taxes & fees
Exceptional
(197 reviews)
Overlook South Haven Harbor steps from South Beach and Downtown
South Haven
S$2,061
for 7 nights, 1 home
S$294 per night
includes taxes & fees
Exceptional
(74 reviews)
5 minute walk to beach or town Sabinas Sandcastle
South Haven
S$4,192
for 7 nights, 1 home
S$599 per night
includes taxes & fees
Exceptional
(82 reviews)
Newly Remodeled Apartment in Downtown South Haven
South Haven
S$1,377
for 7 nights, 1 apartment
S$197 per night
includes taxes & fees
Exceptional
(64 reviews)
Family friendly walk to the beach and town.
South Haven
S$2,491
for 7 nights, 1 apartment
S$356 per night
includes taxes & fees
Exceptional
(185 reviews)
Newly Renovated Cozy Efficiency
South Haven
S$1,698
for 7 nights, 1 apartment
S$243 per night
includes taxes & fees
Exceptional
(139 reviews)
Michiana Apartment #2: Two bedroom one bath apartment in downtown South Haven!
South Haven
S$2,210
for 7 nights, 1 apartment
S$316 per night
includes taxes & fees
Exceptional
(96 reviews)
MICHIANA APARTMENT #3 ONE BDRM/ONE BATH BETWEEN DOWNTOWN AND SOUTH BEACH!
South Haven
S$2,266
for 7 nights, 1 apartment
S$324 per night
includes taxes & fees
Exceptional
(52 reviews)
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
South Haven
S$3,829
for 7 nights, 1 home
S$547 per night
includes taxes & fees
Exceptional
(81 reviews)
Summer Fling 2nd Floor Downtown Suite
South Haven
S$2,279
for 7 nights, 1 apartment
S$326 per night
includes taxes & fees
Exceptional
(30 reviews)
321 Michigan Avenue Historic One Bedroom, One Full Bath Apartment!
South Haven
S$2,221
for 7 nights, 1 apartment
S$317 per night
includes taxes & fees
Exceptional
(63 reviews)
Summer Fling 3rd Floor Downtown Studio
South Haven
S$2,279
for 7 nights, 1 apartment
S$326 per night
includes taxes & fees
Exceptional
(42 reviews)
❤️The Nest❤️ Shot Walk to Beach, Park, Riverfront & Downtown
South Haven
S$3,172
for 7 nights, 1 home
S$453 per night
includes taxes & fees
Exceptional
(128 reviews)
MICHIANA #4: Second floor two bedroom one bath in downtown South Haven!
South Haven
S$2,704
for 7 nights, 1 apartment
S$386 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - South Side
Sweet Pea Cottage | Fire Pit | Walk to Beach
Sleeps 8 · 4 bedrooms · 1+ bathroom
Cozy Beach House: 1 Block to Lake.
Sleeps 8 · 3 bedrooms · 2 bathrooms
Lakefront Home w/Pool, Hot Tub, Firepit & Private Beach!
Sleeps 12 · 5 bedrooms · 4 bathrooms
Waters Reach: Family-Friendly Luxury & South Haven's Best Views
Sleeps 12 · 4 bedrooms · 4+ bathrooms
Two Blocks from the beach & Kids Corner close to Riverwalk and Downtown
Sleeps 10 · 3 bedrooms · 3 bathrooms
Victorian Painted Lady --- A Stroll from South Beach
Sleeps 12 · 5 bedrooms · 3 bathrooms
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Can I find a holiday rental in South Side?
Yes, there are holiday rentals close to the most popular sights in South Side, or you can select a more secluded option if you're looking for a relaxing stay.
How many holiday rentals will I find in South Side?
With 117 Expedia holiday rentals, you're guaranteed to find just the right place for your South Side stay.
What can I see and do in South Side?
While exploring the area, visit family-friendly sights like Michigan Maritime Museum, or get outside and enjoy nature at South Beach. Southside Municipal Marina and South Haven Lighthouse are a couple of places you'll find in the wider area.
What are holiday rentals like in South Side?
Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Side. Holiday rentals feature extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a small group gathering.