South Side holiday rentals
We found 437 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:15 Jan - 22 Jan
Exceptional
(6 reviews)
Beautiful North Beach Home! Private pool! Outdoor recreation area! 12 guests!
South Haven
S$22,738
for 7 nights, 1 home
S$3,248 per night
includes taxes & fees
Exceptional
(84 reviews)
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
South Haven
S$3,702
for 7 nights, 1 home
S$529 per night
includes taxes & fees
Exceptional
(47 reviews)
Prime location! Dog friendly; close to beach, restaurants, shops! New kitchen!
South Haven
S$4,117
for 7 nights, 1 home
S$588 per night
includes taxes & fees
Exceptional
(106 reviews)
INDIANA AVENUE BEACH HOUSE 5 BDRMS. 4 BATHS. ACCOMMODATES TWELVE GUESTS!
South Haven
S$11,606
for 7 nights, 1 home
S$1,658 per night
includes taxes & fees
Exceptional
(100 reviews)
Walk to Beach & Downtown • River + Lake Views • Huge 3-Level Home Sleeps 16
South Haven
S$4,270
for 7 nights, 1 home
S$610 per night
includes taxes & fees
Exceptional
(17 reviews)
FALL SPECIAL! Sweet Haven-3 B/2 B Cottage-Close 2 Downtown & Lake w/ Hot Tub
South Haven
S$3,531
for 7 nights, 1 home
S$504 per night
includes taxes & fees
Exceptional
(78 reviews)
5 minute walk to beach or town Sabinas Sandcastle
South Haven
S$4,210
for 7 nights, 1 home
S$601 per night
includes taxes & fees
Exceptional
(8 reviews)
Private, Firepit, Walk to Town & <1 Mi to Beach
South Haven
S$2,836
for 7 nights, 1 home
S$405 per night
includes taxes & fees
Exceptional
(68 reviews)
Fun inside or out with game room, fenced yard and 1/2 mile to beach or town.
South Haven
S$2,357
for 7 nights, 1 home
S$337 per night
includes taxes & fees
Exceptional
(43 reviews)
❤️The Nest❤️ Shot Walk to Beach, Park, Riverfront & Downtown
South Haven
S$3,217
for 7 nights, 1 home
S$460 per night
includes taxes & fees
Exceptional
(68 reviews)
Located in the heart of Downtown, just a few minute walk to South Beach.
South Haven
S$3,077
for 7 nights, 1 apartment
S$440 per night
includes taxes & fees
Exceptional
(191 reviews)
Newly Renovated Cozy Efficiency
South Haven
S$1,935
for 7 nights, 1 apartment
S$276 per night
includes taxes & fees
Exceptional
(86 reviews)
Newly Remodeled Apartment in Downtown South Haven
South Haven
S$1,213
for 7 nights, 1 apartment
S$173 per night
includes taxes & fees
Exceptional
(38 reviews)
321 Michigan Avenue Historic One Bedroom, One Full Bath Apartment!
South Haven
S$1,820
for 7 nights, 1 apartment
S$260 per night
includes taxes & fees
Exceptional
(204 reviews)
Overlook South Haven Harbor steps from South Beach and Downtown
South Haven
S$2,304
for 7 nights, 1 apartment
S$329 per night
includes taxes & fees
Exceptional
(144 reviews)
Michiana Apartment #2: Two bedroom one bath apartment in downtown South Haven!
South Haven
S$2,092
for 7 nights, 1 apartment
S$299 per night
includes taxes & fees
Exceptional
(98 reviews)
MICHIANA APARTMENT 3 ONE BDRM/ONE BATH BETWEEN DOWNTOWN AND SOUTH BEACH!
South Haven
S$2,673
for 7 nights, 1 apartment
S$382 per night
includes taxes & fees
Exceptional
(69 reviews)
Family friendly walk to the beach and town.
South Haven
S$2,902
for 7 nights, 1 apartment
S$415 per night
includes taxes & fees
Exceptional
(108 reviews)
2 blocks from Lake Michigan family friendly
South Haven
S$2,902
for 7 nights, 1 apartment
S$415 per night
includes taxes & fees
Exceptional
(56 reviews)
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
South Haven
S$3,645
for 7 nights, 1 home
S$521 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
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Chalet
Find the best place to stay - South Side
2 Blocks to Beach | Block to Kids Park | Fire Pit | Coffee Bar
Sleeps 8 · 4 bedrooms · 2 bathrooms
Victorian Painted Lady --- A Stroll from South Beach
Sleeps 12 · 5 bedrooms · 3 bathrooms
Bluffside Splendor: Pool, Hot Tub & Panoramic Lake Views
Sleeps 12 · 5 bedrooms · 5+ 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
Family Friendly Lake Cottage
Sleeps 8 · 3 bedrooms · 2 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.