South Side holiday lettings
We found 434 holiday rentals — enter your dates for availability
Discover a selection of 115 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:11 Dec - 18 Dec
Exceptional
(47 reviews)
Prime location! Dog friendly; close to beach, restaurants, shops! New kitchen!
South Haven
£2,313
for 7 nights, 1 home
£330 per night
includes taxes & fees
Exceptional
(68 reviews)
AVERY STREET BEACH HOUSE. SLEEPS TWELVE! SIX BEDROOMS! FOUR BATHS!
South Haven
£8,353
for 7 nights, 1 home
£1,193 per night
includes taxes & fees
Exceptional
(32 reviews)
Casa de Sarno. Short Walk to Lake Michigan Beach. Dog Friendly.
South Haven
£4,563
for 7 nights, 1 home
£652 per night
includes taxes & fees
Exceptional
(106 reviews)
INDIANA AVENUE BEACH HOUSE 5 BDRMS. 4 BATHS. ACCOMMODATES TWELVE GUESTS!
South Haven
£3,000
for 7 nights, 1 home
£429 per night
includes taxes & fees
Exceptional
(98 reviews)
Walk to Beach & Downtown • River + Lake Views • Huge 3-Level Home Sleeps 16
South Haven
£2,647
for 7 nights, 1 home
£378 per night
includes taxes & fees
Exceptional
(53 reviews)
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
South Haven
£2,147
for 7 nights, 1 home
£307 per night
includes taxes & fees
Exceptional
(39 reviews)
THE OAKLAND NORTH! ACCOMMODATES TEN GUESTS! 4 BDRMS/3 BATHS! NORTH BEACH!
South Haven
£3,341
for 7 nights, 1 home
£477 per night
includes taxes & fees
Exceptional
(76 reviews)
5 minute walk to beach or town Sabinas Sandcastle
South Haven
£2,404
for 7 nights, 1 home
£343 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
£1,323
for 7 nights, 1 home
£189 per night
includes taxes & fees
Exceptional
(85 reviews)
Newly Remodeled Apartment in Downtown South Haven
South Haven
£684
for 7 nights, 1 apartment
£98 per night
includes taxes & fees
Exceptional
(201 reviews)
Overlook South Haven Harbor steps from South Beach and Downtown
South Haven
£1,181
for 7 nights, 1 home
£169 per night
includes taxes & fees
Exceptional
(107 reviews)
2 blocks from Lake Michigan family friendly
South Haven
£1,631
for 7 nights, 1 apartment
£233 per night
includes taxes & fees
Exceptional
(66 reviews)
Family friendly walk to the beach and town.
South Haven
£1,631
for 7 nights, 1 apartment
£233 per night
includes taxes & fees
Exceptional
(8 reviews)
Private, Firepit, Walk to Town & <1 Mi to Beach
South Haven
£1,408
for 7 nights, 1 home
£201 per night
includes taxes & fees
Exceptional
(187 reviews)
Newly Renovated Cozy Efficiency
South Haven
£1,099
for 7 nights, 1 apartment
£157 per night
includes taxes & fees
Exceptional
(18 reviews)
Beach Front, Pool, Short walk to Downtown. Look No more! Peaceful Paradise
South Haven
£1,851
for 7 nights, 1 apartment
£264 per night
includes taxes & fees
Exceptional
(142 reviews)
Michiana Apartment #2: Two bedroom one bath apartment in downtown South Haven!
South Haven
£1,174
for 7 nights, 1 apartment
£168 per night
includes taxes & fees
Exceptional
(97 reviews)
MICHIANA APARTMENT 3 ONE BDRM/ONE BATH BETWEEN DOWNTOWN AND SOUTH BEACH!
South Haven
£1,054
for 7 nights, 1 apartment
£151 per night
includes taxes & fees
Exceptional
(84 reviews)
Summer Fling 2nd Floor Downtown Suite
South Haven
£1,295
for 7 nights, 1 apartment
£185 per night
includes taxes & fees
Exceptional
(65 reviews)
Summer Fling 3rd Floor Downtown Studio
South Haven
£1,295
for 7 nights, 1 apartment
£185 per night
includes taxes & fees
Exceptional
(83 reviews)
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
South Haven
£2,071
for 7 nights, 1 home
£296 per night
includes taxes & fees
Exceptional
(131 reviews)
MICHIANA #4: Second floor two bedroom one bath in downtown South Haven!
South Haven
£1,895
for 7 nights, 1 apartment
£271 per night
includes taxes & fees
Exceptional
(31 reviews)
321 Michigan Avenue Historic One Bedroom, One Full Bath Apartment!
South Haven
£1,237
for 7 nights, 1 apartment
£177 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
Two Blocks from the beach & Kids Corner close to Riverwalk and Downtown
Sleeps 10 · 3 bedrooms · 3 bathrooms
Cozy Beach House: 1 Block to Lake.
Sleeps 8 · 3 bedrooms · 2 bathrooms
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
Top rated rentals - South Side
Weekend Get Away
We enjoyed our stay. The house was new and centrally located. We would recommend this property.
Timothy D.
Stayed Jan 2025
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, 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 115 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.