Holiday rentals with a pool in South Haven

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in South Haven

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

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Top Guest favourite

Cottage in New Buffalo

4.95 out of 5 average rating, 40 reviews

Luxury Cottage with pool; summer will book fast

The madrona cottage is the perfect vacation home. You will fall in love with the cottage and the location, New Buffalo is amazing. The home has 4 full bedrooms and 3.5 baths. It will sleep 8 guests easy. Everything you need to enjoy a nice vacation is included in the place. The cottage has been completely rehabbed with all spaces being brand new. It's has a heated pool and is close to the beach. Relax by the fire or enjoy the game room with a pool table, card table and games. Great for families.

Top Guest favourite

Home in Stevensville

5 out of 5 average rating, 55 reviews

Guest favorite! Quiet setting w/heated pool & more

Welcome to our SW Michigan retreat! This freshly updated home in a quiet country setting feels far away from it all but is close to everything Harbor Country has to offer including beaches, dunes, breweries & shopping. With 5 bedrooms & 3.5 baths, there's enough space for your large family or multiple families to relax & enjoy plentiful amenities including heated pool (seasonal), hot tub, trampoline, fire pit, large yard, multiple outdoor dining areas, woods with paved walking path, WiFi & more!

Guest favourite

Home in South Haven

4.88 out of 5 average rating, 67 reviews

The Oasis Retreat

The Oasis Retreat, located right outside downtown South Haven, is perfect for year round adventures & only 4 block walk from downtown. It boasts a heated pool, hot tub, outdoor bar, backyard, 2nd unit, & fire pit. Ideal for families it includes Wi-Fi, kitchen, laundry, patio, outdoor bar, outhouse, & more. Hot tub: All Year Pool: May - October *weather permitting* If unavailable, consider our nearby properties: 1) https://www.airbnb.com/slink/PSGEaadD 2) https://www.airbnb.com/slink/R5t9UwVUk

Guest favourite

Home in Holland

4.96 out of 5 average rating, 114 reviews

The Splash Pad- a secluded pool/hot tub oasis

The Splash Pad is a perfect getaway for families and groups. Our goal is to bring people together for quality time so we created spaces that everyone will love: the (non heated) pool, hot tub, patio, volleyball net and horse shoes, fire pit, indoor gas fireplace, and a spacious living room with a 55in TV. We hope you explore all the local attractions like: beaches, shops, restaurants, breweries, and hiking trails- all within 4 miles of The Splash Pad! Just added a Level 2 EV charger!! Available

Guest favourite

Condo in Saugatuck

4.93 out of 5 average rating, 102 reviews

Robyn's Mt.Baldhead Nest #3 WaterView of Mt.Baldy

Located at the heart of downtown Saugatuck, this top floor, king bed, nesting spot with river view of Mt. Baldhead, surrounds you with the best of Saugatuck! Enjoy being steps away from the water, park, rentals, Chain Ferry, Star of Saugatuck, restaurants, bars, galleries and shops! RNR nesters also enjoy included seasonal access (Memorial-Oct/7/2024) to the Ship n Shore Hotel waterfront pool & hot tub! RNR is minutes from Lake Michigan, Oval Beach, outstanding wineries, breweries and orchards!

Top Guest favourite

Home in New Buffalo

4.99 out of 5 average rating, 193 reviews

Designer Cottage - walking distance to downtown

Dream cottage getaway just over an hour from downtown Chicago. Walking distance from the beach, restaurants and all of downtown New Buffalo. Close to the casino, wineries and breweries. Whether driving in or taking the train, The Bradford is a relaxing yet sophisticated getaway. Eat, drink, and enjoy the beach, the pool, the shops and incredible summer sunsets, all within walking distance! Please note pool/bathhouse open late May - September and is shared with our association.Permit C22-0051

Guest favourite

Home in West Olive

4.97 out of 5 average rating, 143 reviews

July 5-12&19-26 Open Mini Resort Indoor Pool&Sauna

JULY 5-12 Available!! Current Open May 11-23 June 26-28 July 5-12, 19-26 Aug 9-17 Aug 20-30 3 night min *NO PARTIES &no persons outside of your originally contracted group may visit the property during your stay.* This property is a perfect getaway situated between Holland, Grand Haven & Grand Rapids right on Lakeshore Dr. Our home sits up on a hill overlooking a beautiful 6 acre pond. You will feel as though you are at your own personal resort w/private heated indoor pool & sauna for 6!

Top Guest favourite

Apartment in Douglas

4.96 out of 5 average rating, 23 reviews

Douglas/Saugatuck Duplex Heated Pool Open Now!

Welcome to the Cabana on Blue Star! You'll feel like you're in paradise with our tropical decor.🌴 Relax by the HEATED POOL (spring and summer months) or our 2nd floor deck. Explore the surrounding quaint towns and beaches in Saugatuck and Douglas. Oval Beach is 7 minutes away. Saugatuck Dunes State Park is within walking or biking distance. We have 2 bicycles 🚲 on site for your use. Visit our local Wineries, Distilleries, and Breweries as well as Virtue Cider. Great times are waiting!❤️

Guest favourite

Cottage in South Haven

5 out of 5 average rating, 26 reviews

Pool & hot tub, Lake MI access, theatre room

Amazing home built in 2020 has so many qualities in a great location. Lake Michigan private neighborhood beach access by a tram (elevator to beach), heated pool & hot tub surrounded by a deck & patio. Check out the 5 bedrooms with 2 master suites, 2 living areas, 4 flat screens, a spectacular screened in porch that includes dining & fire table with sectional seating. Enjoy a stocked kitchen, game, theatre & bunk rooms, swing set, fire pit make this home an easy pick!

Guest favourite

Home in Saint Joseph

4.96 out of 5 average rating, 24 reviews

Poolside Oasis - Private Heated Pool + Fun Games

Escape to our stunning 4-bed, 1.5-bath home with a private in-ground pool! Bright living spaces, a fully equipped kitchen, cozy bedrooms, and an amazing heated pool await. Conveniently located near charming Saint Joseph, Michigan, with Lake Michigan's sandy shores and vibrant downtown nearby. Indulge in local cuisine, explore nature trails, then return to the comfort of our inviting home. Your ultimate vacation experience awaits! Book now for an unforgettable getaway!

Guest favourite

Home in Bridgman

5 out of 5 average rating, 5 reviews

The Poolside Escape | Hot Tub | Arcade | Ping Pong

Welcome to "The Poolside Escape" brought to you by Book N Gather vacation rentals. Discover a beautifully renovated single-story ranch with a finished basement, just minutes from Southwest Michigan’s best beaches, state parks, and wineries. Perfect for families or friends, The Poolside Escape offers modern amenities, including a private pool, hot tub, and entertainment options, to make your getaway truly unforgettable. Pool open Memorial Day to September 15th

Top Guest favourite

Cottage in Union Pier

4.96 out of 5 average rating, 202 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!