Vacation rentals with a pool in Sawyer, Weesaw Township

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Top-rated rentals with a pool in Sawyer, Weesaw Township

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Top guest favorite

Cottage in New Buffalo

4.95 out of 5 average rating, 39 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 favorite

Guesthouse in Michigan City

4.99 out of 5 average rating, 115 reviews

“Treetops” Charming Country Coach House

Second-floor comfortably furnished coach house. Stylish and airy space with full kitchen. Great views. Private in-ground 20' x 40' swimming pool reserved exclusively for you and your guests. Basketball half-court. Softball diamond. Bocce court. Great for bicyclists. 20 acres of woods. Hiking trails on property and pond with wildlife. Centrally located between New Buffalo, MI, and Michigan City, IN. Close to the Indiana Dunes, and Lake Michigan. 70 minutes to Chicago, 45 minutes to South Bend.

Top guest favorite

Home in New Buffalo

4.99 out of 5 average rating, 192 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

Top guest favorite

Home in Three Oaks

5 out of 5 average rating, 33 reviews

Private! Cherry Beach Pool House

2025 Summer: July 4-11, Aug 15-22, Aug 22-29 Get away to Harbor County on this private ¾ acre, open concept home two blocks from Cherry Beach with a large PRIVATE heated pool and hot tub! This home has an open floor plan with natural light filling the spacious living areas. Relax in the 3 seasons room or go for a swim in a ‘15x45’ heated saltwater pool, soak in the hot tub, or roast marshmallows by firepit. New - Universal EV charger. Check our NEW listing - Warren Woods Pool Retreat!

Superhost

Home in Three Oaks

4.8 out of 5 average rating, 5 reviews

Gray Haven: Stunning Woodland Retreat w/ Pool

Set on a 1.25-acre wooded lot less than two miles from Townline Beach, this luxurious home is a vacation dream! The open design of the living room, dining room, and kitchen, high ceilings, majestic stone fireplace, and natural light draw you in. Elegant furnishings and stylish decor, plus a pool, huge deck, and screened gazebo invite you to relax. Gather around the kitchen’s large center island or breakfast nook for coffee. Relax by the outdoor fireplace and count the stars. Boom.

Guest favorite

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!

Superhost

Home in Union Pier

4.84 out of 5 average rating, 170 reviews

New Buffalo / Union Pier Pool Hot tub 6 Bedroom

Relax with the whole family at this peaceful home with Classic European style meets Lake Michigan! This astonishing turnkey home is the perfect escape from life in the busy city. The home is ideal for entertaining Famliy . 5 bed , 4 bath , hot tub and gas grille and( pool opens June 6) close to union pier beaches and wine country . Property is nestled in a quaint country road location 1/2 mile off re arrow highway. Room for 10 cars,blue stone patios,ping pong table .

Superhost

Home in Bridgman

5 out of 5 average rating, 4 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 favorite

Cottage in Union Pier

4.96 out of 5 average rating, 200 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!

Guest favorite

Cottage in New Buffalo

4.96 out of 5 average rating, 104 reviews

Casa Playa New House in Union Pier w/ 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!

Superhost

Home in New Buffalo

4.75 out of 5 average rating, 4 reviews

New Buffalo Pool/Hot-tub/Firepit

Your family will be close to everything when you stay at this centrally-located place. This five bedroom 3 bath home has it all including pool, hot-tub, firepit, fenced yard. Steps from a the association beach (small beach currently) walking distance to the large public beach, town, and marina. Renovated in 2023.

Superhost

Home in Union Pier

4.97 out of 5 average rating, 32 reviews

Private Heated Pool and Hot Tub!

This three-bedroom, 2.5 bathroom home sits within a very large fenced-in yard and has lots of privacy. Your group will love the large, private heated pool (16x40) and hot tub to soak your cares away! The backyard fire pit is great for s'mores and starry nights (marshmallow sticks and firewood included)!