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

Living room transitions to the kitchen with a peninsula with 4 bar stools.
The riverwalk is great for viewing the many boats visiting the harbor.
Kitchen leads to the sunroom with overlooks the heated pool in the backyard.
Kitchen was fully updated in 2018.
Exceptional
(82 reviews)

Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB

South Haven

8% off
S$3,691
for 7 nights, 1 home
S$527 per night
includes taxes & fees
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
Stairs down to Main Level
Back Deck
Front Sitting Room
Front Porch
Exceptional
(32 reviews)

Casa de Sarno. Short Walk to Lake Michigan Beach. Dog Friendly.

South Haven

8% off
S$7,773
for 7 nights, 1 home
S$1,110 per night
includes taxes & fees
Casa de Sarno. Short Walk to Lake Michigan Beach. Dog Friendly.
Brand new wraparound deck and railings
Pass through from kitchen to dining room
Bedroom #2, 2nd floor, primary bedroom-Queen memory foam mattress, and futon
Dining room
Exceptional
(46 reviews)

Prime location! Dog friendly; close to beach, restaurants, shops! New kitchen!

South Haven

8% off
S$4,079
for 7 nights, 1 home
S$583 per night
includes taxes & fees
Prime location! Dog friendly; close to beach, restaurants, shops! New kitchen!
View from top of sundeck on poohouse
Entrance to patio
Living area
Pool
Exceptional
(188 reviews)

1-bedroom cottage steps to Lake Michigan Beach fire pit

South Haven

10% off
S$2,740
for 7 nights, 1 cottage
S$391 per night
includes taxes & fees
1-bedroom cottage steps to Lake Michigan Beach fire pit
Dining
Custom natural oak wood trim on the fireplace surround.
The foyer and master suite are located adjacent to the Living Room.
Living area
Exceptional
(67 reviews)

AVERY STREET BEACH HOUSE. SLEEPS TWELVE! SIX BEDROOMS! FOUR BATHS!

South Haven

9% off
S$14,001
for 7 nights, 1 home
S$2,000 per night
includes taxes & fees
AVERY STREET BEACH HOUSE. SLEEPS TWELVE! SIX BEDROOMS! FOUR BATHS!
Gourmet kitchen with bar seating for 6
Back deck, firepit/chairs (on left), dining table, grill, bench seating
Sunset from third level
River view from ground level deck back of house
Exceptional
(97 reviews)

Walk to Beach & Downtown • River + Lake Views • Huge 3-Level Home Sleeps 16

South Haven

8% off
S$4,699
for 7 nights, 1 home
S$671 per night
includes taxes & fees
Walk to Beach & Downtown • River + Lake Views • Huge 3-Level Home Sleeps 16
lake view
Totally Remodeled Kitchen
View From the Patio
Comfortable living room with View of Lake Michigan
Exceptional
(18 reviews)

Beach Front, Pool, Short walk to Downtown. Look No more! Peaceful Paradise

South Haven

8% off
S$3,254
for 7 nights, 1 apartment
S$465 per night
includes taxes & fees
Beach Front, Pool, Short walk to Downtown. Look No more! Peaceful Paradise
Outdoor dining
Private kitchen
Beach
Private kitchen
Exceptional
(39 reviews)

THE OAKLAND NORTH! ACCOMMODATES TEN GUESTS! 4 BDRMS/3 BATHS! NORTH BEACH!

South Haven

8% off
S$5,636
for 7 nights, 1 home
S$805 per night
includes taxes & fees
THE OAKLAND NORTH! ACCOMMODATES TEN GUESTS! 4 BDRMS/3 BATHS! NORTH BEACH!
There is parking for three cars on the driveway as well as on street parking.
Wide and gentle stairs from the driveway to the side door.
Natural travertine tile flooring is installed throughout the kitchen.
Sitting room beyond the family room.
Exceptional
(106 reviews)

INDIANA AVENUE BEACH HOUSE 5 BDRMS. 4 BATHS. ACCOMMODATES TWELVE GUESTS!

South Haven

8% off
S$5,198
for 7 nights, 1 home
S$743 per night
includes taxes & fees
INDIANA AVENUE BEACH HOUSE 5 BDRMS. 4 BATHS. ACCOMMODATES TWELVE GUESTS!
Living area
Property grounds
Property grounds
Exterior detail
Exceptional
(63 reviews)

Fun inside or out with game room, fenced yard and 1/2 mile to beach or town.

South Haven

8% off
S$2,325
for 7 nights, 1 home
S$332 per night
includes taxes & fees
Fun inside or out with game room, fenced yard and 1/2 mile to beach or town.
Room
Beautiful backyard
Master Bath Entrance
Exterior
Exceptional
(106 reviews)

2 blocks from Lake Michigan family friendly

South Haven

9% off
S$2,578
for 7 nights, 1 apartment
S$368 per night
includes taxes & fees
2 blocks from Lake Michigan family friendly
Dining
Property grounds
Private kitchen
Crimson Sun, 
Where the Sidewalk Ends!
Exceptional
(197 reviews)

Overlook South Haven Harbor steps from South Beach and Downtown

South Haven

9% off
S$2,061
for 7 nights, 1 home
S$294 per night
includes taxes & fees
Overlook South Haven Harbor steps from South Beach and Downtown
Front Porch
Kids Corner - Park
1st Flr living rm with
flat screen tv
Front of home . 224 Monroe
Exceptional
(74 reviews)

5 minute walk to beach or town Sabinas Sandcastle

South Haven

8% off
S$4,192
for 7 nights, 1 home
S$599 per night
includes taxes & fees
5 minute walk to beach or town Sabinas Sandcastle
Interior
Marina
Living area
View
Exceptional
(82 reviews)

Newly Remodeled Apartment in Downtown South Haven

South Haven

8% off
S$1,377
for 7 nights, 1 apartment
S$197 per night
includes taxes & fees
Newly Remodeled Apartment in Downtown South Haven
Property grounds
Kitchen
Kitchen
Front of house
Exceptional
(64 reviews)

Family friendly walk to the beach and town.

South Haven

9% off
S$2,491
for 7 nights, 1 apartment
S$356 per night
includes taxes & fees
Family friendly walk to the beach and town.
studio kitchen
back yard
studio bedroom
Back of the house
Exceptional
(185 reviews)

Newly Renovated Cozy Efficiency

South Haven

9% off
S$1,698
for 7 nights, 1 apartment
S$243 per night
includes taxes & fees
Newly Renovated Cozy Efficiency
Exterior
South Haven has several beautiful parks and incredible flowers in the Summer.
Living area
Kitchen with dishwasher, self cleaning gas range and space maker microwave.
Exceptional
(139 reviews)

Michiana Apartment #2: Two bedroom one bath apartment in downtown South Haven!

South Haven

8% off
S$2,210
for 7 nights, 1 apartment
S$316 per night
includes taxes & fees
Michiana Apartment #2: Two bedroom one bath apartment in downtown South Haven!
Michiana #3 kitchen includes all major appliances and cooking utensils.
Aerial photo of South Haven showing the Black River opening into Lake Michigan.
Michiana Apartment #3 Living Room with tall cathedral ceilings and great light!
Vintage Victorian details have been preserved of the exterior front entry.
Exceptional
(96 reviews)

MICHIANA APARTMENT #3 ONE BDRM/ONE BATH BETWEEN DOWNTOWN AND SOUTH BEACH!

South Haven

8% off
S$2,266
for 7 nights, 1 apartment
S$324 per night
includes taxes & fees
MICHIANA APARTMENT #3 ONE BDRM/ONE BATH BETWEEN DOWNTOWN AND SOUTH BEACH!
Farmhouse style dining table
The riverwalk is great for viewing the many boats visiting the harbor.
New patio added in 2018 connecting garage to pool to back yard to side yard.
Remodeled kitchen has stunning quartz countertops and stainless steel appliances
Exceptional
(52 reviews)

Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB

South Haven

8% off
S$3,829
for 7 nights, 1 home
S$547 per night
includes taxes & fees
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
Interior
Interior
Private kitchen
Living area
Exceptional
(81 reviews)

Summer Fling 2nd Floor Downtown Suite

South Haven

8% off
S$2,279
for 7 nights, 1 apartment
S$326 per night
includes taxes & fees
Summer Fling 2nd Floor Downtown Suite
Living area
Spacious Entry Foyer with the laundry closet behind the six panel oak door.
Living area
Private kitchen
Exceptional
(30 reviews)

321 Michigan Avenue Historic One Bedroom, One Full Bath Apartment!

South Haven

8% off
S$2,221
for 7 nights, 1 apartment
S$317 per night
includes taxes & fees
321 Michigan Avenue Historic One Bedroom, One Full Bath Apartment!
Living area
Interior
Interior
Private kitchen
Exceptional
(63 reviews)

Summer Fling 3rd Floor Downtown Studio

South Haven

8% off
S$2,279
for 7 nights, 1 apartment
S$326 per night
includes taxes & fees
Summer Fling 3rd Floor Downtown Studio
Property grounds
Living area
Private kitchen
Interior
Exceptional
(42 reviews)

❤️The Nest❤️ Shot Walk to Beach, Park, Riverfront & Downtown

South Haven

8% off
S$3,172
for 7 nights, 1 home
S$453 per night
includes taxes & fees
❤️The Nest❤️ Shot Walk to Beach, Park, Riverfront & Downtown
Relax on the sun soaked second floor deck at the Michiana Apartment #4!
Aerial view of South Haven and the Black River as it meets Lake Michigan.
The Michiana Apartment #4 with beautiful new sectional sofa in 2024.
Welcome to the Michiana Apartment #4 in beautiful South Haven, Michigan!
Exceptional
(128 reviews)

MICHIANA #4: Second floor two bedroom one bath in downtown South Haven!

South Haven

8% off
S$2,704
for 7 nights, 1 apartment
S$386 per night
includes taxes & fees
MICHIANA #4: Second floor two bedroom one bath in downtown South Haven!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More 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.