Holiday rentals with a pool in Saugatuck

The exterior of a two-story gray and green house is showcased, featuring a stone-accented garage and white-trimmed windows. Lush shrubs line the entrance, and a gravel driveway leads to the garage, set against a backdrop of greenery and a clear blue sky.

5.0 out of 5 average rating, 252 reviews

Driftwood Shores-SH is a great fall getaway!

September and Fall is starting to book! Enjoy a trip to beautiful South Haven along the shores of Lake Michigan. Driftwood Shores is a charming 1,680 sq. ft. home in the Harbor Club Resort. It has everything you need to enjoy a peaceful family vacation, friends getaway, or girls weekend out. NOTE: AirBnb has changed its pricing structure so that now the host pays the 15.5% service fee (instead of the guest.) Your overall cost hasn't changed, but the nightly rate reflects this new payment system.

FamilyValueBeach

4.86 out of 5 average rating, 160 reviews

A charming historic home is nestled among lush greenery and mature trees. The front porch welcomes guests, leading to a warm interior illuminated by soft lighting. The property is surrounded by well-maintained grass and foliage, contributing to the peaceful ambiance.

Home in Douglas

Vintage Splendor Historic

My place is good for couples, solo adventurers, families (with kids), big groups, Girls night outs, and furry friends - with a pet cleaning fee. Vintage Splendor is a beautiful, charming historic home with all today's amenities. We are located in the Village of Douglas and are on The Historic Home Walking Tour. This large home boasts 3 formal bedrooms, 2-1/2 Bathrooms and a den that serves as a 4th bedroom. This Victorian home sleeps 10 with 6 beds (Two King, Two Queen, & a pull out Trundle.

FamilyValueTV

An inviting outdoor area is featured, showcasing a heated pool beside a vibrant garden filled with blooming flowers. Stylish lounge chairs are positioned near the pool, while a shaded bar area is adorned with ferns and colorful blossoms, creating a relaxing retreat.

4.93 out of 5 average rating, 132 reviews

The Oasis Retreat

The Oasis Retreat is a newly remodeled home with a private heated pool & hot tub, just 4 blocks from downtown South Haven & close to Lake Michigan beaches, marina, trails, restaurants, bars & shops. Perfect for families & groups, the private backyard has an outdoor bar, fire pit, gas grill, pizza oven, ping pong, outdoor shower & detached guest unit w/ seasonal bath/shower. Inside: kitchen, laundry, fast WiFi, Roku TVs, heat/AC, sleeper sofa & upstairs loft. Pool: May-Oct Hot tub: Year-round

ValueFamilyTV

4.97 out of 5 average rating, 115 reviews

A bedroom features a spacious bed adorned with white linens and a navy throw blanket. Exposed brick walls add character, complemented by framed ocean-themed art. A mirrored dresser and a closet with hanging space provide ample storage. Natural light filters through a nearby window.

Flat in South Haven

Walk everywhere: Bikes: Pool & hot tub: Beach gear

✨Upscale historic loft building 🚶WALK EVERYWHERE 🕑 2:00 PM CHECK-IN ⭐️Central Loft amenities⭐️ ♨️ Hot tub 🏊‍♂️ Indoor heated pool 🎬 2 movie theaters 💪 Workout room 🏖️ Beach necessities included 🌊 1/2 mile to Lake Michigan 🚲 4 beach cruiser bikes included 🛍️ A block from downtown SoHa 🍷 Near The Lakeshore Wine Trail 🍺 Close to several breweries 🧺 Washer & dryer in condo ☕️ Keurig & standard brewing coffee pot 🧑‍🍳 Fully stocked kitchen ⚡️ High speed inte

LocationFamilyHeating

4.82 out of 5 average rating, 175 reviews

A gated pool area is shown, featuring a vibrant blue swimming pool with floating toys. Surrounding the pool is a concrete deck and a green fence. A white chair and a basketball hoop are visible in the background, adding to the outdoor recreation space.

Home in Holland

Welcome Home *Near Lake Mi Beaches and Downtown*

With only 2 miles to the beach of Holland State Park and 3 miles to downtown Holland where you can enjoy shopping, breweries, restaurants, galleries, Farmers' market and more, this brick house is the perfect home for you and your group. Located on a large property with plenty of space inside and out, this house is comfortable and convenient to all Holland has to offer. We would love to have you stay at our "Home Away From Home"! Pool is open June-Sept. Heated only by sun.

ValueLocationIndoor spaces

A charming two-story building is framed by mature trees with vibrant green leaves and autumn accents. The front door, painted bright yellow, is flanked by decorative lanterns, while large windows with dark shutters provide a welcoming facade. Lush greenery surrounds the entrance.

4.89 out of 5 average rating, 148 reviews

Robyn's Chain Ferry Nest #2

Enjoy nesting in the heart of downtown Saugatuck with a view of the water, park & Chain Ferry, a designated parking spot, hardwood floors throughout, bedroom w KING bed adjoining full bathroom, 40”smart tv, w/ privacy door to living area, w/ sofa bed, 50” smart tv w/YOUTUBETV streaming access w/600MBPS WiFi service, equipped kitchen w/ cooktop, oven, microwave, full refrigerator, dishwasher, washer, dryer, coffee maker, SEASONAL access to Ship n Shore Hotel waterfront Pool &hot tub (May-Sept)

LocationValueDecor

5.0 out of 5 average rating, 113 reviews

The exterior of a two-story home is visible, featuring a welcoming front entrance. A large tree provides shade, with a swing hanging from one of its sturdy branches. Ferns line the landscape, creating a natural border around the property, complemented by a well-maintained lawn.

Home in St. Joseph

4 Bedroom home w/pool in St. Joseph

This home is all about having fun with the family. Open concept kitchen, living room & dining room. Deck off the dining for eating al fresco. Family room & game room area with large screen TV, Nintendo switch, game table with lots of board games & a dart board. Walkout to the pool (unheated) and fire pit area for fun in the sun and evening campfires to roast marshmallows. Outdoor games include bag toss, ladder ball, ring toss. Home is five miles to Silver Beach and downtown Saint Joseph.

FamilyValueHospitality

4.93 out of 5 average rating, 192 reviews

An outdoor heated swimming pool is surrounded by a secure fence, featuring multiple turquoise umbrellas and lounge chairs. Lush green lawns and trees provide a scenic backdrop, enhancing the tranquil atmosphere. The pool area is well-lit by the sun, inviting relaxation.

Home in Fennville

AlleganOrchardsSleeps25Pool,HotTubFireplaceFirepit

ALLEGAN ORCHARDS: Luxe private retreat 5min. to Saugatuck/Douglas/Fennville Lake MI beaches/sand dunes. - Open kitchen - Private heated pool (fees apply - see house rules) - Private outdoor hot tub (open 24/7/365, no fee) - Indoor fireplace - Outdoor fire pit - Screened porch - Game room: Ping pong, billiards, game table, arcade games - Blue tooth sound throughout - Local area: Saugatuck/Douglas ("Art Coast of MI"), award-winning destination: Restos/Antiques/Boat/Hike/Golf/Wineries/Breweries.

LocationFamilyGrill

A secluded in-ground pool is surrounded by lush greenery and landscaped gardens. Several lounge chairs are arranged near the pool, which reflects the sky above. Flowering plants and shrubs frame the scene, creating a peaceful outdoor retreat.

4.84 out of 5 average rating, 201 reviews

Experience Nature-Charming Cottage

Romantic getaway and/or family adventure Quiet updated farmhouse on a quiet road 5 miles from South Haven and Lake Michigan.The Black River runs along the property and there are 3 ponds.There is secluded in ground pool,woods and landscaped grounds for walks Great local markets A guest made a video about his time at the cottage that you can see on You Tube. GoozyVision Trip to South Haven,Michigan July 2017 The video also shows the beach and the town

ValueLocationView

4.97 out of 5 average rating, 173 reviews

The exterior of the Garden House Cottage is framed by lush greenery and landscaped gardens. A charming red barn-style structure features multiple large windows and a metal roof, inviting natural light into the interior spaces.

Barn in Hamilton

The Garden House Cottage at Redbud Farm

It's summer at Redbud Farm! The Garden House Cottage is a beautifully remodeled old farm barn. Modern boho farmhouse style. This place has charm galore. You'll love the peace and quiet of the country and the gardens are professionally landscaped and maintained. Enjoy the views of the English potager style garden right out the window while relaxing on the queen bed. Traveling with friends/family? Check out my other listing The Granary at Redbud Farm.

ValueLocationKitchen

4.97 out of 5 average rating, 268 reviews

Apartment in Douglas

Fun condo perfect for summer and fall fun.

Beautifully updated vacation condo with association pool perfect for spring summer or fall vacation. Close to Lake Michigan and all of the fun activities Saugatuck-Douglas has to offer. Less than 1 mile to Lake Michigan. Close to Douglas and Oval Beaches. Enjoy a drink on your own front porch. One bedroom one bath with a cozy gas fireplace. Additional sleeping for two on pull out couch in the living room. Close to bike path to downtown.

ValueLocationSleep quality

The exterior of the cottage is framed by lush green lawns and vibrant flower beds. A spacious two-car garage is visible on the right. Mature trees and shrubs create a serene atmosphere, while a blue sky with scattered clouds provides a picturesque backdrop.

5.0 out of 5 average rating, 37 reviews

Dogwood Creek, in-town, luxury cottage, pool-sauna

Pool, hot-tub, and outdoor luxury sauna open year round! Relax and unwind with friends and family at Dogwood Creek Cottage. Cozy yet spacious with a walk-to-town location and a five-minute drive to Oval or Douglas beach. Have fun with friends and the whole family in our fabulous space. Enjoy the amazing screened porch and large firepit, and flower gardens. In the fall and winter, cozy up by the fireplace after a long hike or day skiing.

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Popular amenities for Saugatuck rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 123 reviews

Beach-Themed Game Room & Pool Near Lake Michigan

FamilyValueAccess

5.0 out of 5 average rating, 16 reviews

Christine's Cottage | Special Summer Weekday Price

LocationFamilyLayout

A heated saltwater pool is framed by a sunlit deck with multiple lounge chairs overlooking a lush, tree-lined area. Surrounding greenery adds a sense of privacy, creating a tranquil outdoor space for relaxation.

5.0 out of 5 average rating, 53 reviews

Renovated Golf Course Home | Private Pool/Hot Tub

FamilyLocationGrill

5.0 out of 5 average rating, 17 reviews

Heated Pool Open through Oct | Theater | Fire Pit

LocationFamilyAccuracy

A small wooden table with two glasses of red wine is situated on a balcony. Four white stools surround the table. The background displays a serene waterfront view with a colorful sky at sunset, enhancing the outdoor setting.

4.98 out of 5 average rating, 44 reviews

Luxury Lakeview Retreat | Pool | Walk Downtown

ValueLocationCleanliness

5.0 out of 5 average rating, 21 reviews

The modern home is seen from the pool area, showcasing its dark exterior and large windows. A spacious deck is accessed from the rear, surrounded by landscaped greenery, while the inviting blue pool reflects the clear sky above.

Home in Fennville

NEW! Two Oaks: Pond-side oasis with pool/hot tub

FamilyLocationCondition

The exterior of a charming two-story farmhouse is surrounded by vibrant autumn foliage. A gravel driveway leads to the entrance, flanked by colorful landscaping. The house features a mix of dark siding and white trim, complemented by a welcoming front porch adorned with seasonal decorations.

4.79 out of 5 average rating, 19 reviews

Allegan Gardens

ValueFamilyCleanliness

A charming exterior view of a two-story cottage is framed by greenery. The entrance features a covered porch with a bench, welcoming guests. Bright sunlight highlights the warm tones of the house, and a landscaped path of stones leads up to the front door.

5.0 out of 5 average rating, 3 reviews

The Cottage at Forest Inn

FamilyLocationBeach

Apartment rentals with a pool

4.98 out of 5 average rating, 121 reviews

Apartment in South Haven

SunKissed Sanctuary + Pool + Hot Tub +CentralLofts

LocationValueCheck-in

4.96 out of 5 average rating, 45 reviews

Waterfront couples getaway near beach and trails

ValueLocationComfort

4.93 out of 5 average rating, 70 reviews

The open-layout living area features a cozy sofa facing a gas fireplace, with two green armchairs positioned nearby. Large windows allow natural light to fill the space. A colorful wall art piece adds a touch of design, complemented by a coffee table with magazines.

Apartment in Douglas

Northern Lights 2 Bed 2 Bath With Pool

FamilyLocationCheckout

4.9 out of 5 average rating, 41 reviews

Bird's Nest | 2BR | Downtown Saugatuck | Walkable

FamilyLocationComfort

4.92 out of 5 average rating, 13 reviews

Apartment in Douglas

Love the Sun, MI Condo in Douglas, MI

FamilyLocationNearby

A bright living space features a striped couch adorned with decorative pillows. A light wooden coffee table displays a book, and two wooden stools are positioned near a bright kitchen area equipped with white cabinetry and modern appliances.

4.97 out of 5 average rating, 30 reviews

Holiday Hill Apartment 701

FamilyLocationBeach

5.0 out of 5 average rating, 26 reviews

A studio condo features a queen-size Murphy bed with a light-patterned blanket and a cozy futon nearby. A small dining area with a table is positioned adjacent to the fully equipped kitchenette. Soft blue walls and natural light create a relaxed ambiance.

Apartment in South Haven

Private Beach/Pool on Lake MI Condo

ValueFamilyIndoor spaces

5.0 out of 5 average rating, 49 reviews

An aerial view captures a marina lined with boats, surrounded by lush greenery and residential buildings. The water reflects the sky, with scattered clouds and distant hills visible. The scene showcases a vibrant community atmosphere alongside the waterfront.

Apartment in Spring Lake

Luxury Two-Bedroom Condo on the Marina

ValueFamilyKitchen

Other holiday rentals with a pool

5.0 out of 5 average rating, 21 reviews

Cabin in Fennville

Lux Cabin Twin Peaks East • Private Pool & Hot Tub

FamilyLocationAmenities

4.96 out of 5 average rating, 25 reviews

A serene view of a heated association pool surrounded by lush landscaping. The pool area includes lounge chairs and umbrellas, with a scenic backdrop of Lake Kalamazoo. The American flag is visible, fluttering near the water's edge, enhancing the tranquil setting.

Townhouse in Saugatuck

Water views and pool! Walk to downtown!

FamilyLocationPool

5.0 out of 5 average rating, 45 reviews

Flat in Douglas

Summerset Cottage & Suites, King Suite

FamilyLocationBack garden

5.0 out of 5 average rating, 24 reviews

Flat in South Haven

Downtown Loft: Firepit, Pool/Hot Tub, Theater, Gym

FamilyLocationBeach

4.82 out of 5 average rating, 11 reviews

Flat in Saugatuck

Simply Saugy - A Relaxing Saugatuck Getaway!

LocationFamilyRiver

4.87 out of 5 average rating, 54 reviews

An outdoor deck offers a dining area with a round table and four metal chairs, providing views of Kalamazoo Lake. Large glass doors lead into the interior space, while a welcome mat complements the light-colored wooden floor.

Villa in Saugatuck

Mermaid townhouse shared pool walk to Saugatuck!

LocationFamilyNearby

The outdoor area features a sparkling pool surrounded by lounge chairs and umbrellas. A spacious patio is equipped with a large dining table and additional seating, offering a perfect setting for relaxation in a beautifully landscaped backyard.

4.97 out of 5 average rating, 30 reviews

Lamb Guest | Private Pool, Hot Tub, Cabana, Dogs

LocationValueComfort