South Side holiday rentals
We found 434 holiday rentals — enter your dates for availability
Discover a selection of 116 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:4 Dec - 11 Dec
Exceptional
(47 reviews)
Prime location! Dog friendly; close to beach, restaurants, shops! New kitchen!
South Haven
S$4,059
for 7 nights, 1 home
S$580 per night
includes taxes & fees
Exceptional
(67 reviews)
AVERY STREET BEACH HOUSE. SLEEPS TWELVE! SIX BEDROOMS! FOUR BATHS!
South Haven
S$13,932
for 7 nights, 1 home
S$1,990 per night
includes taxes & fees
Exceptional
(32 reviews)
Casa de Sarno. Short Walk to Lake Michigan Beach. Dog Friendly.
South Haven
S$7,734
for 7 nights, 1 home
S$1,105 per night
includes taxes & fees
Exceptional
(106 reviews)
INDIANA AVENUE BEACH HOUSE 5 BDRMS. 4 BATHS. ACCOMMODATES TWELVE GUESTS!
South Haven
S$5,173
for 7 nights, 1 home
S$739 per night
includes taxes & fees
Exceptional
(98 reviews)
Walk to Beach & Downtown • River + Lake Views • Huge 3-Level Home Sleeps 16
South Haven
S$4,676
for 7 nights, 1 home
S$668 per night
includes taxes & fees
Exceptional
(53 reviews)
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
South Haven
S$3,810
for 7 nights, 1 home
S$544 per night
includes taxes & fees
Exceptional
(39 reviews)
THE OAKLAND NORTH! ACCOMMODATES TEN GUESTS! 4 BDRMS/3 BATHS! NORTH BEACH!
South Haven
S$5,609
for 7 nights, 1 home
S$801 per night
includes taxes & fees
Exceptional
(76 reviews)
5 minute walk to beach or town Sabinas Sandcastle
South Haven
S$4,171
for 7 nights, 1 home
S$596 per night
includes taxes & fees
Exceptional
(65 reviews)
Fun inside or out with game room, fenced yard and 1/2 mile to beach or town.
South Haven
S$2,314
for 7 nights, 1 home
S$331 per night
includes taxes & fees
Exceptional
(201 reviews)
Overlook South Haven Harbor steps from South Beach and Downtown
South Haven
S$2,051
for 7 nights, 1 home
S$293 per night
includes taxes & fees
Exceptional
(107 reviews)
2 blocks from Lake Michigan family friendly
South Haven
S$2,848
for 7 nights, 1 apartment
S$407 per night
includes taxes & fees
Exceptional
(66 reviews)
Family friendly walk to the beach and town.
South Haven
S$2,848
for 7 nights, 1 apartment
S$407 per night
includes taxes & fees
Exceptional
(186 reviews)
Newly Renovated Cozy Efficiency
South Haven
S$1,919
for 7 nights, 1 apartment
S$274 per night
includes taxes & fees
Exceptional
(6 reviews)
Private, Firepit, Walk to Town & <1 Mi to Beach
South Haven
S$2,404
for 7 nights, 1 home
S$343 per night
includes taxes & fees
Exceptional
(141 reviews)
Michiana Apartment #2: Two bedroom one bath apartment in downtown South Haven!
South Haven
S$2,068
for 7 nights, 1 apartment
S$295 per night
includes taxes & fees
Exceptional
(18 reviews)
Beach Front, Pool, Short walk to Downtown. Look No more! Peaceful Paradise
South Haven
S$3,238
for 7 nights, 1 apartment
S$463 per night
includes taxes & fees
Exceptional
(97 reviews)
MICHIANA APARTMENT #3 ONE BDRM/ONE BATH BETWEEN DOWNTOWN AND SOUTH BEACH!
South Haven
S$1,867
for 7 nights, 1 apartment
S$267 per night
includes taxes & fees
Exceptional
(83 reviews)
Summer Fling 2nd Floor Downtown Suite
South Haven
S$2,267
for 7 nights, 1 apartment
S$324 per night
includes taxes & fees
Exceptional
(83 reviews)
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
South Haven
S$3,672
for 7 nights, 1 home
S$525 per night
includes taxes & fees
Exceptional
(65 reviews)
Summer Fling 3rd Floor Downtown Studio
South Haven
S$2,267
for 7 nights, 1 apartment
S$324 per night
includes taxes & fees
Exceptional
(42 reviews)
❤️The Nest❤️ Shot Walk to Beach, Park, Riverfront & Downtown
South Haven
S$3,156
for 7 nights, 1 home
S$451 per night
includes taxes & fees
Exceptional
(131 reviews)
MICHIANA #4: Second floor two bedroom one bath in downtown South Haven!
South Haven
S$3,385
for 7 nights, 1 apartment
S$484 per night
includes taxes & fees
Exceptional
(31 reviews)
321 Michigan Avenue Historic One Bedroom, One Full Bath Apartment!
South Haven
S$2,210
for 7 nights, 1 apartment
S$316 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
Lakefront Home w/Pool, Hot Tub, Firepit & Private Beach!
Sleeps 12 · 5 bedrooms · 4 bathrooms
Cozy Beach House: 1 Block to Lake.
Sleeps 8 · 3 bedrooms · 2 bathrooms
Two Blocks from the beach & Kids Corner close to Riverwalk and Downtown
Sleeps 10 · 3 bedrooms · 3 bathrooms
South Beach
Sleeps 12 · 4 bedrooms · 2 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 116 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.