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:11 Dec - 18 Dec

Bedroom #2, 2nd floor, primary bedroom-Queen memory foam mattress, and futon
Pass through from kitchen to dining room
Dining room
Brand new wraparound deck and railings
9.6/10Exceptional (47 reviews)

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

South Haven

8% off
S$4,072
S$582 per night
includes taxes & fees
Prime location! Dog friendly; close to beach, restaurants, shops! New kitchen!
The Avery Street Beach House accommodates twelve (12) guests maximum.
Custom natural oak wood trim on the fireplace surround.
Living area
Dining
10/10Exceptional (68 reviews)

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

South Haven

9% off
S$13,893
S$1,985 per night
includes taxes & fees
AVERY STREET BEACH HOUSE. SLEEPS TWELVE! SIX BEDROOMS! FOUR BATHS!
Front Sitting Room
Back Deck
Stairs down to Main Level
Front Sitting Room
10/10Exceptional (32 reviews)

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

South Haven

8% off
S$7,773
S$1,110 per night
includes taxes & fees
Casa de Sarno. Short Walk to Lake Michigan Beach. Dog Friendly.
Sitting room beyond the family room.
Wide and gentle stairs from the driveway to the side door.
There is parking for three cars on the driveway as well as on street parking.
Natural travertine tile flooring is installed throughout the kitchen.
9.8/10Exceptional (106 reviews)

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

South Haven

8% off
S$5,150
S$736 per night
includes taxes & fees
INDIANA AVENUE BEACH HOUSE 5 BDRMS. 4 BATHS. ACCOMMODATES TWELVE GUESTS!
Sunset from third level
Back deck, firepit/chairs (on left), dining table, grill, bench seating
River view from ground level deck back of house
View of kitchen and dining from large family sitting area
9.4/10Exceptional (98 reviews)

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

South Haven

8% off
S$4,680
S$669 per night
includes taxes & fees
Walk to Beach & Downtown • River + Lake Views • Huge 3-Level Home Sleeps 16
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
10/10Exceptional (53 reviews)

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

South Haven

8% off
S$3,798
S$543 per night
includes taxes & fees
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
Outdoor dining
Private kitchen
Dining
Private kitchen
10/10Exceptional (39 reviews)

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

South Haven

8% off
S$5,641
S$806 per night
includes taxes & fees
THE OAKLAND NORTH! ACCOMMODATES TEN GUESTS! 4 BDRMS/3 BATHS! NORTH BEACH!
Front Porch
Kids Corner - Park
Kitchen - new stainless steal appliances
Front of home . 224 Monroe
10/10Exceptional (76 reviews)

5 minute walk to beach or town Sabinas Sandcastle

South Haven

8% off
S$4,165
S$595 per night
includes taxes & fees
5 minute walk to beach or town Sabinas Sandcastle
Interior
Property grounds
Property grounds
Exterior detail
9.8/10Exceptional (65 reviews)

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

South Haven

8% off
S$2,307
S$330 per night
includes taxes & fees
Fun inside or out with game room, fenced yard and 1/2 mile to beach or town.
TV area
Marina
Interior
Living area
10/10Exceptional (85 reviews)

Newly Remodeled Apartment in Downtown South Haven

South Haven

8% off
S$1,205
S$172 per night
includes taxes & fees
Newly Remodeled Apartment in Downtown South Haven
Property grounds
Living area
Interior
Private kitchen
10/10Exceptional (42 reviews)

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

South Haven

8% off
S$3,182
S$455 per night
includes taxes & fees
❤️The Nest❤️ Shot Walk to Beach, Park, Riverfront & Downtown
Private kitchen
Property grounds
Terrace/patio
Dining
10/10Exceptional (201 reviews)

Overlook South Haven Harbor steps from South Beach and Downtown

South Haven

9% off
S$2,044
S$292 per night
includes taxes & fees
Overlook South Haven Harbor steps from South Beach and Downtown
Master Bath Entrance
Beautiful backyard
Exterior
Screened in porch
10/10Exceptional (107 reviews)

2 blocks from Lake Michigan family friendly

South Haven

9% off
S$2,840
S$406 per night
includes taxes & fees
2 blocks from Lake Michigan family friendly
Front of house
Kitchen
Kitchen
Property grounds
10/10Exceptional (66 reviews)

Family friendly walk to the beach and town.

South Haven

9% off
S$2,840
S$406 per night
includes taxes & fees
Family friendly walk to the beach and town.
Interior
Outdoor dining
Exterior detail
Dining
10/10Exceptional (7 reviews)

Private, Firepit, Walk to Town & <1 Mi to Beach

South Haven

11% off
S$2,466
S$352 per night
includes taxes & fees
Private, Firepit, Walk to Town & <1 Mi to Beach
studio kitchen
back yard
Back of the house
apartment c
10/10Exceptional (186 reviews)

Newly Renovated Cozy Efficiency

South Haven

9% off
S$1,913
S$273 per night
includes taxes & fees
Newly Renovated Cozy Efficiency
Living area
South Haven has several beautiful parks and incredible flowers in the Summer.
Kitchen with dishwasher, self cleaning gas range and space maker microwave.
South Bedroom with queen bed.
9.8/10Exceptional (141 reviews)

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

South Haven

8% off
S$2,070
S$296 per night
includes taxes & fees
Michiana Apartment #2: Two bedroom one bath apartment in downtown South Haven!
lake view
Totally Remodeled Kitchen
View From the Patio
View of Lake Michigan from the Living room
10/10Exceptional (18 reviews)

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

South Haven

8% off
S$3,225
S$461 per night
includes taxes & fees
Beach Front, Pool, Short walk to Downtown. Look No more! Peaceful Paradise
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.
9.8/10Exceptional (97 reviews)

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

South Haven

8% off
S$1,863
S$266 per night
includes taxes & fees
MICHIANA APARTMENT 3 ONE BDRM/ONE BATH BETWEEN DOWNTOWN AND SOUTH BEACH!
Interior
Interior
Living area
Private kitchen
9.8/10Exceptional (83 reviews)

Summer Fling 2nd Floor Downtown Suite

South Haven

8% off
S$2,260
S$323 per night
includes taxes & fees
Summer Fling 2nd Floor Downtown Suite
Kitchen leads to the sunroom with overlooks the heated pool in the backyard.
The riverwalk is great for viewing the many boats visiting the harbor.
Kitchen was fully updated in 2018.
Easy moving between pool and hot tub to warm up and cool off!
10/10Exceptional (83 reviews)

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

South Haven

8% off
S$3,661
S$523 per night
includes taxes & fees
Perfect for Family - HEATED POOL thru early Oct, WALK to Downtown/Beach, HOT TUB
Room
Interior
Interior
Living area
10/10Exceptional (65 reviews)

Summer Fling 3rd Floor Downtown Studio

South Haven

8% off
S$2,260
S$323 per night
includes taxes & fees
Summer Fling 3rd Floor Downtown Studio
The Michiana Apartment #4 with beautiful new sectional sofa in 2024.
Aerial view of South Haven and the Black River as it meets Lake Michigan.
Welcome to the Michiana Apartment #4 in beautiful South Haven, Michigan!
Relax on the sun soaked second floor deck at the Michiana Apartment #4!
9.8/10Exceptional (131 reviews)

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

South Haven

8% off
S$3,370
S$481 per night
includes taxes & fees
MICHIANA #4: Second floor two bedroom one bath in downtown South Haven!
Living area
Spacious Entry Foyer with the laundry closet behind the six panel oak door.
Private kitchen
Terrace/patio
10/10Exceptional (31 reviews)

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

South Haven

8% off
S$2,210
S$316 per night
includes taxes & fees
321 Michigan Avenue Historic One Bedroom, One Full Bath Apartment!

  • 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 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.