Vacation 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.

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Guest favourite

Guesthouse 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.

Mar. 20 – 27

$97 CAD per night

Superhost

Cabin in Benton Harbor

4.91 out of 5 average rating, 288 reviews

Cozy Cabin by Nature

We deep clean and sanitize after every guest. Enjoy social distancing in this completely renovated cabin in a picturesque setting with 2 ponds. Dog friendly. A full kitchen to cook your own meals. Xbox one is provided to watch movies and relax. Enjoy outdoors with the fire pit. We are dog friendly. We do ask 3 things if you bring your furry family with you. Please keep them off the furniture, clean up after their business and keep them leashed when around other guests as the property is shared

May 22 – 29

$480 CAD per night

Superhost

Camper/RV 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!

Jan. 27 – Feb. 3

$257 CAD per night

Guest favourite

Tiny homes in Sawyer

4.92 out of 5 average rating, 61 reviews

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!

Jan. 18 – 25

$350 CAD per night

Guest favourite

Home in Sawyer

5.0 out of 5 average rating, 7 reviews

Las Moras, 6 Acres & Large Pool

Come and enjoy Nature at Las Moras (“The Berries” in Spanish) with rows of blueberry bushes, watch the deer prance through the front yard, see the wild turkeys in the woods, watch the turtles in the pond as you enjoy the 25x30 salt water heated pool, surrounded by a beautiful forest and flowering shrubs, in a stunning setting. The renovated cottage is in a secluded 6 acres, surrounded by an open land preserve, all of this is close to Downtown Sawyer and Cherry Beach, 90 minutes from Chicago

Feb. 4 – 11

$895 CAD 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.

May 6 – 13

$471 CAD per night

Guest favourite

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.

Dec. 14 – 21

$224 CAD 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!

Feb. 2 – 9

$1,031 CAD 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!

Nov. 29 – Dec. 6

$696 CAD 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 .

Jan. 9 – 16

$313 CAD per night

Guest favourite

Tiny homes in Sawyer

4.97 out of 5 average rating, 35 reviews

Sandy Feet Retreat

Welcome to Sandy Feet Retreat! We are excited for you to visit our family-friendly home with a cozy living room, fireplace and a full kitchen! There is a shared heated pool on site. 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! Due to space limitations we have a 2-car maximum for parking.

Apr. 7 – 14

$481 CAD per night

Guest favourite

Guesthouse in Cassopolis

4.97 out of 5 average rating, 100 reviews

2 person cottage with pool and hottub

Come for a relaxing getaway in the country. Cook in our small kitchenette or use our pellet grill or fire pit. Located in a small hobby farm setting with cows, sheep, & chickens roaming the pasture. We also have 3 kittens 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 soak in the hot tub and let the worries of life melt away during your stay.

Aug. 27 – Sep. 3

$279 CAD per night