Holiday rentals with a pool in Grand Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Grand Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Guest house in Valparaiso

4.96 out of 5 average rating, 161 reviews

Private Cottage in Gated Nudist Community

We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is mandatory. Pricing on club website. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area . The cottage is sanitized after every rental. Fresh baked muffins are available in the morning.

16–23 Jan

$86 SGD per night

Guest favourite

Home in Michiana Shores

4.93 out of 5 average rating, 85 reviews

Splash (Pool! Hot Tub!) at Aqua House by the Lake

Family fun in Michiana Shores. Situated on one-half acre, enjoy the private heated eco-friendly pool (open May-Sept), year-round hot tub, large yard with 2 pooldeck fire pits, Weber crafted grill, bball, ping pong, hammock, biking, and nearby tennis/pickle ball all surrounded by mature forested trees. Indoors relax with billiards, 2 flatscreens for gametime, 3 bedrooms plus pullout living room sofa, woodburning fireplace, mudroom for your stuff, and a serene enclosed patio for dining and hosting

10–17 Dec

$578 SGD per night

Superhost

Campervan/Motorhome in Porter

4.79 out of 5 average rating, 609 reviews

'Pool Barn Camper' w/Hot Tub near Indiana Dunes

Pool is open! Hot tub open all year! Fully equipped RV is parked in the driveway of our Pool Barn. RV sleeps 6, has bath w/shower, stove, microwave, heat & A/C, & running water all year. We are located minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hiking in the Indiana Dunes National Park along the Little Calumet River and the historic Bailley homestead is only 1 block away. You may also use our large pool, hot tub, grill, campfire, and playground area. No cleaning fee!

24–31 Dec

$228 SGD per night

Superhost

Home in Grand Beach

4.89 out of 5 average rating, 9 reviews

Amazing Grand Beach Vacay Home-Pool, Hot Tub,

This spacious, captivating 6BR/3.5BA home in a golf-cart friendly area has a huge back yard and pool, hardwood floors and a 2-story great room, plus a stone fireplace flanked by huge windows! The gourmet kitchen has a granite-top island and hi-end appliances. The upper-level Master suite features a gas fireplace and private balcony with Lake Michigan views. The lounge area has a Peloton bike. 3 main-floor BRs share 2 full baths. A screened porch overlooks the rear deck and a pool, fire pit and

11–18 Jan

$1,026 SGD per night

Superhost

Home in Michiana

4.78 out of 5 average rating, 18 reviews

Comfy Cottage-Heated Pool, 1 Block to Beach!

Instantly feel at home in this quintessential Classic Lake Cottage! So close to the lake you’ll catch a view of it from the front porch. Bring your family & friends as there’s plenty of space with 13 beds, kids area, extra family/TV room, & amazing screened in porch in the back overlooking the lush yard, pool, & fire pit. Imagine kids playing in the yard, days at the beach, sunsets over the lake, grilling on the BBQ, and S’mores & laughs around the fire. *Pool Open late April through Mid-Oct*

28 Oct – 4 Nov

$673 SGD per night

Guest favourite

Home in Michigan City

4.97 out of 5 average rating, 151 reviews

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Beautiful home in the heart of Beachwalk, across the street from Lake Kai, pools, basketball & tennis courts and 2 blocks to Lake Michigan. This home is bursting with charm. Front porch runs the width of the house. Dining area opens up to family room with a lovely fireplace. Stunning master bedroom w/walk-in closet and beautiful new bathroom with all the finishes. 3 more bedrooms upstairs, one with full bathroom attached and the other 2 sharing bathroom. 5th bedroom on the lower level.

13–20 Mar

$474 SGD per night

Guest favourite

Home in Three Oaks

4.9 out of 5 average rating, 103 reviews

Luxe Life | Heated Pool | Hot Tub| Sleeps 10

Important notes: - Home is in HARBERT by the lakefront, NOT in Three Oaks - Hot tub open all year - Pool closed from October 23, 2023 through Memorial Day 2024 After a day of exploring Lake Michigan, Warren Dunes, or New Buffalo (just a quick 10-minute drive away), find your sanctuary at Mae's Place. Recharge by soaking in the inviting hot tub, sizzle up a delicious meal on the grill or in the kitchen, and cap off the evening around the fire pit while toasting marshmallows.

6–13 May

$397 SGD per night

Guest favourite

Serviced apartment in New Buffalo

5.0 out of 5 average rating, 16 reviews

Charming 1BR/1BA Retreat with private beach access

This airy space holds warmth in the details — wooden accents, walls the color of pine and sage, the faint smell of a campfire. One king bed features a cushy Casper mattress topped with plush Sferra linens. The bathroom, complete with Malin+Goetz bath products, keep things fresh. A small but mighty kitchenette is home to your morning coffee thanks to a Moccamaster coffee machine, fridge + microwave. If you must remain connected to the real world, the WiFi and TV are solid.

2–9 Dec

$194 SGD per night

Guest favourite

Cottage in New Buffalo

4.94 out of 5 average rating, 140 reviews

Perfect Get Away - Private Hot Tub - Lots of Room

Gorgeous, New Buffalo cottage in the heart of New Buffalo. Perfect for families and friends ~ many areas for gathering within the home. Private hot tub off the back screened in porch and only ten steps away from large community pool. Walk to everything in NB - Whittaker is only 2 blocks away. Enjoy close proximity: beach, amazing restaurants in town (Stray Dog, Redamak's, etc.). The private hot tub makes this perfect place for social distancing with Family!

22–29 Apr

$916 SGD per night

Guest favourite

Cottage in Union Pier

4.96 out of 5 average rating, 173 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, pool, hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax and unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today and create lasting memories!

25 Dec – 1 Jan

$771 SGD per night

Guest favourite

Home in New Buffalo

4.91 out of 5 average rating, 266 reviews

Farmesque with a splash of modern

Turn back time with trough sinks and claw foot tub and cedar beams ,distressed floors and walls with a mix of modern. Galien river marsh across street full of nature and several bikes on property for your riding pleasure . Newly built 2019 , 3 blocks from Main Street downtown New Buffalo.6 blocks from beach , enjoy all local spots and coffee shop and grocery steps away . Dead end street in very quaint neighborhood, covered front porch enclosed rear porch .

9–16 Jan

$264 SGD per night

Superhost

Guest house in Michigan City

4.87 out of 5 average rating, 120 reviews

Lagunitas Coach House in Beachwalk, Lake Michigan

Lagunitas Coach House is a sought after location on the quaint Thomas blvd cul de sac. It is the coach house to Gooch Life. It is the perfect get away spot for a couple or small family wanting to escape to the beautiful beach of Lake Michigan. Lagunitas and Gooch Life share the property but are separate structures. Lagunitas has a private entrance, amenities, and parking. Lagunitas sleeps 6, see pictures for bed configuartion.

9–16 May

$176 SGD per night