South Side holiday rentals
We found 429 holiday rentals — enter your dates for availability
Discover a selection of 113 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:25 Dec - 1 Jan

Exceptional
(69 reviews)
AVERY STREET BEACH HOUSE. SLEEPS TWELVE! SIX BEDROOMS! FOUR BATHS!
South Haven
S$13,847
for 7 nights, 1 home
S$1,978 per night
includes taxes & fees

Exceptional
(32 reviews)
Casa de Sarno. Short Walk to Lake Michigan Beach. Dog Friendly.
South Haven
S$7,788
for 7 nights, 1 home
S$1,113 per night
includes taxes & fees

Exceptional
(55 reviews)
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
South Haven
S$6,358
for 7 nights, 1 home
S$908 per night
includes taxes & fees

Exceptional
(106 reviews)
INDIANA AVENUE BEACH HOUSE 5 BDRMS. 4 BATHS. ACCOMMODATES TWELVE GUESTS!
South Haven
S$5,183
for 7 nights, 1 home
S$740 per night
includes taxes & fees

Exceptional
(99 reviews)
Walk to Beach & Downtown • River + Lake Views • Huge 3-Level Home Sleeps 16
South Haven
S$4,638
for 7 nights, 1 home
S$663 per night
includes taxes & fees

Exceptional
(78 reviews)
5 minute walk to beach or town Sabinas Sandcastle
South Haven
S$5,148
for 7 nights, 1 home
S$735 per night
includes taxes & fees

Exceptional
(67 reviews)
Fun inside or out with game room, fenced yard and 1/2 mile to beach or town.
South Haven
S$2,275
for 7 nights, 1 home
S$325 per night
includes taxes & fees

Exceptional
(42 reviews)
❤️The Nest❤️ Shot Walk to Beach, Park, Riverfront & Downtown
South Haven
S$3,134
for 7 nights, 1 home
S$448 per night
includes taxes & fees

Exceptional
(203 reviews)
Overlook South Haven Harbor steps from South Beach and Downtown
South Haven
S$2,302
for 7 nights, 1 home
S$329 per night
includes taxes & fees

Exceptional
(108 reviews)
2 blocks from Lake Michigan family friendly
South Haven
S$2,790
for 7 nights, 1 apartment
S$399 per night
includes taxes & fees

Exceptional
(67 reviews)
Family friendly walk to the beach and town.
South Haven
S$2,790
for 7 nights, 1 apartment
S$399 per night
includes taxes & fees

Exceptional
(190 reviews)
Newly Renovated Cozy Efficiency
South Haven
S$1,892
for 7 nights, 1 apartment
S$270 per night
includes taxes & fees

Exceptional
(36 reviews)
321 Michigan Avenue Historic One Bedroom, One Full Bath Apartment!
South Haven
S$2,232
for 7 nights, 1 apartment
S$319 per night
includes taxes & fees

Exceptional
(18 reviews)
Beach Front, Pool, Short walk to Downtown. Look No more! Peaceful Paradise
South Haven
S$3,258
for 7 nights, 1 apartment
S$465 per night
includes taxes & fees

Exceptional
(97 reviews)
MICHIANA APARTMENT 3 ONE BDRM/ONE BATH BETWEEN DOWNTOWN AND SOUTH BEACH!
South Haven
S$1,971
for 7 nights, 1 apartment
S$282 per night
includes taxes & fees

Exceptional
(143 reviews)
Michiana Apartment #2: Two bedroom one bath apartment in downtown South Haven!
South Haven
S$2,091
for 7 nights, 1 apartment
S$299 per night
includes taxes & fees

Exceptional
(85 reviews)
Summer Fling 2nd Floor Downtown Suite
South Haven
S$2,290
for 7 nights, 1 apartment
S$327 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$5,310
for 7 nights, 1 home
S$759 per night
includes taxes & fees

Exceptional
(67 reviews)
Summer Fling 3rd Floor Downtown Studio
South Haven
S$2,290
for 7 nights, 1 apartment
S$327 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - South Side

Two Blocks from the beach & Kids Corner close to Riverwalk and Downtown
Sleeps 10 · 3 bedrooms · 3 bathrooms

Lakefront Home w/Pool, Hot Tub, Firepit & Private Beach!
Sleeps 12 · 5 bedrooms · 4 bathrooms

2 Blocks to Beach | Block to Kids Park | Fire Pit | Coffee Bar
Sleeps 8 · 4 bedrooms · 2 bathrooms

Bluffside Splendor: Pool, Hot Tub & Panoramic Lake Views
Sleeps 12 · 5 bedrooms · 5+ 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 113 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 Surfari Joe's Indoor Wilderness Water Park, 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.
