A pier extending into the water at sunset with a lighthouse in the distance.

South Side holiday lettings

We found 435 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:22 Jan - 29 Jan

Easy moving between pool and hot tub to warm up and cool off!

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.

Living room transitions to the kitchen with a peninsula with 4 bar stools.

Exceptional

(84 reviews)

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

South Haven

8% off

£2,135

for 7 nights, 1 home

£305 per night

includes taxes & fees

Pass through from kitchen to dining room

Corner house, this side faces Kalamazoo Street

Bedroom #2, 2nd floor, primary bedroom-Queen memory foam mattress, and futon

Exceptional

(47 reviews)

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

South Haven

8% off

£2,381

for 7 nights, 1 home

£340 per night

includes taxes & fees

Natural travertine tile flooring is installed throughout the kitchen.

Wide and gentle stairs from the driveway to the side door.

Aspiring and seasoned cooks have reason to rejoice in the beautiful kitchen!

There is parking for three cars on the driveway as well as on street parking.

Exceptional

(106 reviews)

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

South Haven

8% off

£6,838

for 7 nights, 1 home

£977 per night

includes taxes & fees

Back deck, firepit/chairs (on left), dining table, grill, bench seating

View of kitchen and dining from large family sitting area

Exceptional

(100 reviews)

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

South Haven

8% off

£2,441

for 7 nights, 1 home

£349 per night

includes taxes & fees

Colorful Living Room with Comfortable Modular Sofa

Lower Level TV space with sofa bed (full-size futon)

Exceptional

(17 reviews)

FALL SPECIAL! Sweet Haven-3 B/2 B Cottage-Close 2 Downtown & Lake w/ Hot Tub

South Haven

8% off

£2,019

for 7 nights, 1 home

£288 per night

includes taxes & fees

Kitchen - new stainless steal appliances

Exceptional

(78 reviews)

5 minute walk to beach or town Sabinas Sandcastle

South Haven

8% off

£2,446

for 7 nights, 1 home

£349 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

9% off

£1,338

for 7 nights, 1 home

£191 per night

includes taxes & fees

The half acre property offers a private space.

Exceptional

(8 reviews)

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

South Haven

7% off

£1,112

for 7 nights, 1 home

£159 per night

includes taxes & fees

Exceptional

(43 reviews)

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

South Haven

8% off

£1,854

for 7 nights, 1 home

£265 per night

includes taxes & fees

Above a storefront is where you’ll find The Nest. It’s a pretty cool spot.

Exceptional

(69 reviews)

Located in the heart of Downtown, just a few minute walk to South Beach.

South Haven

8% off

£1,824

for 7 nights, 1 apartment

£261 per night

includes taxes & fees

Exceptional

(191 reviews)

Newly Renovated Cozy Efficiency

South Haven

9% off

£1,112

for 7 nights, 1 apartment

£159 per night

includes taxes & fees

Exceptional

(86 reviews)

Newly Remodeled Apartment in Downtown South Haven

South Haven

16% off

£689

for 7 nights, 1 apartment

£98 per night

includes taxes & fees

Exceptional

(204 reviews)

Overlook South Haven Harbor steps from South Beach and Downtown

South Haven

9% off

£1,336

for 7 nights, 1 apartment

£191 per night

includes taxes & fees

Kitchen with dishwasher, self cleaning gas range and space maker microwave.

South Haven has several beautiful parks and incredible flowers in the Summer.

Exceptional

(144 reviews)

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

South Haven

8% off

£1,211

for 7 nights, 1 apartment

£173 per night

includes taxes & fees

Vintage Victorian details have been preserved of the exterior front entry.

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!

Michiana #3 kitchen includes all major appliances and cooking utensils.

Exceptional

(98 reviews)

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

South Haven

9% off

£1,542

for 7 nights, 1 apartment

£220 per night

includes taxes & fees

Exceptional

(69 reviews)

Family friendly walk to the beach and town.

South Haven

9% off

£1,661

for 7 nights, 1 apartment

£237 per night

includes taxes & fees

Exceptional

(110 reviews)

2 blocks from Lake Michigan family friendly

South Haven

9% off

£1,661

for 7 nights, 1 apartment

£237 per night

includes taxes & fees

New patio added in 2018 connecting garage to pool to back yard to side yard.

Heated Pool and Yard (views from master bedroom)

Exceptional

(57 reviews)

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

South Haven

12% off

£2,103

for 7 nights, 1 home

£300 per night

includes taxes & fees

Find spaces that suit your style

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Cottage

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Chalet

Find the best place to stay - South Side

Premier Host

2 Blocks to Beach | Block to Kids Park | Fire Pit | Coffee Bar

Sleeps 8 · 4 bedrooms · 2 bathrooms

Premier Host

Lakefront Home w/Pool, Hot Tub, Firepit & Private Beach!

Sleeps 12 · 5 bedrooms · 4 bathrooms

Family Friendly Lake Cottage

Sleeps 8 · 3 bedrooms · 2 bathrooms

Premier Host

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

Victorian Painted Lady --- A Stroll from South Beach

Sleeps 12 · 5 bedrooms · 3 bathrooms

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.