
Holiday rentals with a pool in Sawyer
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Sawyer
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Fabulous designer owned home w/ heated pool & spa!
Fabulous designer owned home with heated pool & spa in the heart of Sawyer--the ultimate Harbor Country getaway. Renovation has been recently completed at this amazing 5 bedrooms, 5 bath home w/ heated pool and year-round spa. Wonderful, spacious residence with multiple living areas, two fireplaces, & fully stocked dream kitchen. Secondary family room in lower level. Newly landscaped yard designed w/ privacy in mind w/ fire pit, dining folly, and fully fenced yard w/multi-level deck. Perfection!

Anchors Away - Sawyer, MI
Welcome to our home! We are so excited to get to share our home with you! Our family-friendly has a cozy living room, fireplace and a full kitchen! On site is a heated pool, laundry mat, and it’s home to the Beach Bucket the best spot for amazing ice cream, homemade popcorn and fudge! Directly across the street is Warren Dunes State Park. The 3/4 mile walk, drive or bike ride gets you to the beach for a fun filled day! Climb the dunes, lay in the sand, go for a swim, relax-you’re on vacation!

Luxury home with pool.
Plan your next family gathering, winery tour, football weekend, or simply hang by the pool (seasonal) in this spacious and well-appointed home. Perfectly located in the charming town of New Carlisle, approx 16 miles to New Buffalo, Michigan, and approx 17 miles to Notre Dame. This spacious, tastefully decorated home features a gourmet kitchen, private office, large family room with gas fireplace. The outdoors boasts a heated in-ground pool (seasonal), bbq, and wood-burning fireplace.

Wabi Sabi Chic at The Flamingo Ranch in Lakeside
NOW BOOKING SUMMER 2026 at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. ONE WEEK RENTALS ONLY DURING SUMMER, FRIDAY CHECK IN. This designer-owned haven offers both deep seclusion + an open-format layout that invites connection, healing + memory-making. Whether you’re gathering with family, reuniting with old friends, or seeking a rejuvenating escape, we deliver an experience that’s as comfortable + stylish as it is energetically charged.

Willow Dunes – Hot Tub, Pool & Near Beach Fun
Soak, splash & explore! Unwind in private hot-tub, cool off in pool and reach Lake Michigan’s sandy beaches in minutes. 4 comfy bedrooms, open-concept living area, fast Wi-Fi, well-stocked kitchen. Year-round hot tub Seasonal pool access Smart TV & game room Washer/dryer Easy drive to wineries, breweries, and dunes. Plenty of parking and private bike storage—perfect for family meet-ups or friends’ getaways. Have questions? We respond quickly—book now before your dates disappear!

Designer Cottage Relax Pool Beach & Spa—Windjammer
Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, community pool, private 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! Create lasting memories!

Pool, Hot tub, Kayaks, Waterfront, SW Michigan
Waterfront property with a private hot tub, pool, and tennis court, making it an ideal destination for those seeking both relaxation and recreation. Visit beautiful Southwest Michigan and stay at the St. Joe Overlook. Take a swim in the pool, unwind in the hot tub, take the kayaks out for a river cruise, or sit by the fire. Enjoy this stunning location and top-notch amenities. A trip to the St Joe Overlook is the perfect place to gather & reconnect. Maximum Guest Count 16.

The Fern: 2BR, Hot Tub, Fire Pit, Walk to Beach
Presenting Townie 4 - The Fern, part of the unique Townie Cottages collection. This newly built lakeside luxury home was designed exclusively by Kate Marker Interiors (recognized by Architectural Digest and Luxe Home). Located in Union Pier, these exquisite cottages blend rustic charm and modern elegance for an unforgettable stay. Immerse yourself in a meticulously curated interior with high-end finishes and chic furnishings, creating a sophisticated yet homey atmosphere.

Casa Playa - Union Pier Home w/ Pool & Private Spa
This 4 bedroom getaway is located in the heart of Harbor Country and is just a 10 minute walk or 3 minute drive to the best beach in Union Pier! Casa Playa has EVERYTHING a vacation house can offer: an association POOL, a private HOT TUB, high speed internet that accommodates many people working from home, a cozy indoor fireplace, an outdoor fire pit, an outdoor deck & grill, 2 smart Tvs, ALL brand new appliances, and games for the whole family!

Cottage for two with hot tub near Swiss Valley!
Come for a relaxing getaway in the country. Cook in our small kitchenette or use our Blackstone or fire pit. Located in a small hobby farm setting with sheep roaming the pasture. We also have a couple cats that claim the pool area as their own. The long driveway and gravel road are perfect for a leisurely stroll to enjoy the great outdoors. Take a swim in the pool or a soak in the hot tub and let the worries of life melt away during your stay.

New buffalo Farmstead main home pool hot tub
5 bedroom 2 bath 2200 sq ft modern farmstead , 2 minutes to new buffalo and beach and all its offerings , 18x36 new heated shared pool and hot tub. Property on 6 acres with plenty of room for kids to play , 26 apple trees and woods , ride host bikes to new buffalo .. Best of both worlds in country , close to town .There’s 2 new homes on 6 acre property, this home and 1 guest home ( rented separately) .

Just Updated in Lakeside | Pool + Hot Tub + Porch!
Enjoy a newly updated cottage with unique finishes, an enormous screened porch, and a private pool and hot tub. Located just down the street from central Lakeside in Harbor Country, Michigan. A five-minute bike ride to the lake and a 10-minute drive from downtown Sawyer, New Buffalo, and Three Oaks - Lakeside Landing is a relaxing escape in any season to enjoy all that Southwest Michigan has to offer.
Popular amenities for Sawyer rentals with a pool
House rentals with a pool

Beautiful home in Beachwalk/Notre Dame weekends

Modern Lake House w/ Private Pool near New Buffalo

5 Bedroom Luxury Home In Heart of Beachwalk Resort

The Keystone Ranch…The only house on the block!

4 Bedroom home w/pool in St. Joseph

New Buffalo Pool/Hot-tub/Firepit

Modern 5-Bedroom New Buffalo Lakeside Escape

Hot Tub | Backyard Oasis | Game Room | |Coffee Bar
Apartment rentals with a pool

Large 3BR w/ pool and parking - near everything

Union Pier Condo with Association Heated Pool.

(2026 OPEN!) Union Pier Condo With Heated Pool.

Idyllic New Buffalo Condo: Walk to Beach & Shops!

Fall 2 nt min Perfect Location Condo Pools Walk to

Amazing Beach Condo with pool and great sunsets!

New Buffalo Condo with Association Pool and Beach!

Nightingale Dunes - Modern beach town retreat
Other holiday rentals with a pool

Rosie’s Cottage close to Warren Dunes (w pool)

Luxe by the Lake - Pool Access - Walk to Beaches

Heart of Notre Dame|King Bed|WiFi|Gym|Shuttle Bus

Beautiful, sunny 4 BR home with pool and hot tub

Hot tub open year round and pvt association beach!

Marina Sunset: Marina Lights & Holiday Nights

Woodside

Secluded Escape Hot Tub Heated Pool 24 Acre Villa
When is the best time to visit Sawyer?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $536 SGD | $498 SGD | $440 SGD | $522 SGD | $665 SGD | $779 SGD | $836 SGD | $771 SGD | $659 SGD | $504 SGD | $578 SGD | $578 SGD |
| Avg. temp | -4°C | -3°C | 3°C | 9°C | 15°C | 20°C | 22°C | 22°C | 18°C | 11°C | 4°C | -1°C |
Quick stats about holiday rentals with a pool in Sawyer

Total holiday rentals
Explore 30 holiday rentals in Sawyer

Nightly prices starting at
Sawyer holiday rentals start at $206 SGD per night before taxes and fees

Verified guest reviews
Over 1,590 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Sawyer holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Sawyer rentals

4.9 Average rating
Sawyer stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Cabin rentals Sawyer
- Cottage rentals Sawyer
- House rentals Sawyer
- Rentals with lake access Sawyer
- Rentals with outdoor seating Sawyer
- Rentals with a firepit Sawyer
- Rentals with a hot tub Sawyer
- Pet-friendly rentals Sawyer
- Rentals with a washing machine and dryer Sawyer
- Rentals with a fireplace Sawyer
- Rentals with beach access Sawyer
- Flat rentals Sawyer
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- Family-friendly rentals Sawyer
- Rentals with pools Berrien County
- Rentals with pools Michigan
- Rentals with pools United States
- University of Notre Dame
- Warren Dunes State Park
- Washington Park Zoo
- Silver Beach Carousel
- Potato Creek State Park
- Deep River Waterpark
- Point O' Woods Golf & Country Club
- Woodlands Course at Whittaker
- Culver Academies Golf Course
- Elcona Country Club
- The Dunes Club
- Lost Dunes Golf Club
- South Bend Country Club
- Indiana Dunes State Park
- Warren Golf Course
- Kennedy Water Park
- Cogdal Vineyards
- Shady Creek Winery
- Dablon Winery and Vineyards
- 12 Corners Vineyards
- Four Winds Casino




