
Pet-friendly holiday rentals in Grand Beach
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Top-rated pet-friendly home rentals in Grand Beach
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Popular amenities for Grand Beach pet-friendly home rentals
Pet-friendly house rentals

The Bright Yellow Retreat
We loved how close this cute little house was to the downtown area. It was clean and tidy, beds were firm, but ok. It has a nice big yard, with plenty of outdoor seating. Would recommend.

South Shore Studio Apartment {National Park}
We had a wonderful stay in Chesterton, IN! Robert was a fantastic host—friendly, responsive, and made us feel right at home. One of the highlights was the Sunday open mic night—such a great local vibe and community spirit. My wife and I are already planning to come back. We left a small gift—a door harp—as a token of our appreciation. There was already a nail on the bathroom door, and it just fits perfectly for this cozy getaway. Legend says it repels negative energy and welcomes the positive—hope it adds a little charm for future guests. Thanks again, Robert!

Anna's Cottage
We loved Rob’s house and would stay here again. The backyard and screen porch were wonderful. The house was clean and the beds were comfortable. It was a short walk to restaurants, shopping and the beach. Highly recommend!

Casa Gitana - Boutique Style Stay in Three Oaks
We thoroughly enjoyed our stay! The space is beautiful and we felt right at home. Brooke was so helpful and responsive to any questions we had. Highly recommend!

CASA TICA Serenity Amongst Nature Dog Friendly
We really enjoyed staying at Elena’s place. The location is great, it’s very peaceful and private, but at the same time close to the town. The house itself was clean and cozy. Elena was very nice to talk to, very helpful, friendly and responsive. A perfect place for a getaway.

Cozy House near Beach, Casino, Outlets, & Hiking
Very clean house, very close to the beach. Has everything you need for a short visit. We packed 7 people in without feeling too cramped.

Debs Michigan hot tub house, open all year
Thank you so much for opening your beautiful home to us for our getaway trip. It was the perfect place for an out of town trip. I’ll definitely be recommending your place to friends, and I hope to return in the future.

1 Block to Journeyman - Dog Friendly/Patio/Firepit
Kristin's spot was perfect for our family. We were in Three Oaks for a wedding. Both the welcome party and the reception were within easy walking distance. The house was clean and well equipped. It had everything we needed for a weekend long celebration!
Pet-friendly home rentals with a pool

Private 2 Bed/2 Bath Cottage, Pool, Beach Access
Wish there were a few games/books/activies in the unit other than that great place clean and modern.

Dunescape Beach Retreat, Downtown New Buffalo
We had a great stay! The house was perfect. It was nice and clean with a great rooftop deck and screened in porch. The location could not have been better, walking distance to everything in town. Everything was easy as far as check in and check out with a book explaining everything in the house. Mark was great at responding to questions. I would highly recommend staying here.

Private Cabin Retreat - Heart of Harbor Country
Loved our stay! The house was very nice and clean

Lakeside cottage w/htd pool/pvt beach 7 min walk
Amazing trip for our family. The home was clean, beautiful and the location was wonderful with walkable restaurants and places to get coffee, groceries. The pool was perfect for our kids. We felt right at home :) Our host was great and extremely responsive to any messages. Looking forward to a future trip.

The Keystone Ranch…The only house on the block!
Great stay! Loved the pool and lanai. Had fun playing the board games from the 80s and 90s. Great, well equipped kitchen - even a blender for smoothies! Linens were amazingly comfortable.

Pool, Hot tub, Kayaks, Waterfront, SW Michigan
We had a lovely family reunion at St Joe’s overlook. Kitchen came with literally everything- all sorts of cooking instruments (crock pot, air fryer, toaster etc), spices/oils, and zip lock bags for leftovers. All brand new appliances and ample prep space. We got the pool heated and it was wonderful! Very large size to fit all the family kids. The hot tub was a nice save for the adults who were freezing. Beautiful views from the living room of the river with ample and comfy seating. The home was perfect for a large gathering. We appreciate Evan and Claire hosting us they were always responsive and helpful.

Designer Cottage Relax Beach Pool & Spa—Windjammer
Lovely home, many well thought out perks like fans in upstairs rooms and beach toys for kids! Info said it was an easy short walk to beach so I spent a whole lot more than I usually would. With children it would not be pleasant and is really not a short walk (and is on a semi busy road) & beach is down a whole lot of steps. BUT there are parking spaces so it was fine. Within the house, the steps are fairly steep at parts & there are 2?big ones going into house &!these were hard for my 70 year old mom w knee issues. So if person reading reviews is one of those people, this might not be THE place. That being said, it is very short walk to community pool & host is very responsive & house is beautiful! My mom mostly stayed within first floor including an awesome bed/bath on ground floor. There are games (although I didn’t love the Ouija board 🫣😂) . This would be a great place for multiple family / friends to split cost ;) Its very beautiful & community pool & hot tub are great!

Perfect Get Away - Private Hot Tub - Lots of Room
This is our 5th year of vacationing in New Buffalo and have stayed at Missy's place on 3 of those visits! The house works beautifully for our family (7 adults and 4 kids under 6 yo) and you're never tripping over each other, which makes it so relaxing! We'll be back!!
Private, pet-friendly home rentals

Bright Scandinavian-style cottage w/ private yard
Loved this cute little cottage! Very well decorated and the accommodations were great. Great location as well. Alannah and Nick were extremely accommodating and responsive. I would definitely visit again!

SoulShine Inn • Pets Welcome•Fully fenced backyard
This place was super adorable. My friends and I needed a weekend away and this was the perfect place. Everything was super clean. There’s coffee, teas, all sorts of cookware to use, it was just super easy. It’s the name on the board when you walk in was a great touch. Hope to stay here again soon and highly recommend!!

The Luna Cottages - Unit 3 - Private Beach Access!
The most adorable cottage and getaway for my husband and I! I am picky and this one checked all the boxes. We loved being right across the street from the private access beach, walkable to Whistle Stop, comfortable and super clean accommodations - everything feels well thought out from the sheets to the design choices and we appreciated all of the details. We will definitely be back!

Charming Cottage - Hot Tub, Sauna, Large Yard
We loved our stay at Ashley and Bobby’s! The yard was great for our dogs and the beach, sauna and hot tub were great for us. Perfect spot for a peaceful week away. Bobby and Ashley were extremely accommodating and responsive to any needs. They have a beautiful home and I hope we can return!!

Lake Trail Cottage(NO Cleaning Fee!)
My family and I had a lovely summer Indiana Dunes weekend at Jill’s place. The house was clean, cozy, and well-stocked. We loved the bikes and covered back porch. It was nice to be right on the Calumet trail, in biking distance to beaches. We took a 25 minute drive to Garwood’s and came home with a boatload of strawberries, and took a beautiful sunset dip in Lake Michigan. Thanks for the fun weekend!

Spacious+2 Primary Bedrooms+Beach Access+GolfCart
We were 2 families staying at the house and it was the perfect place to make so many memories! The downstairs living space and bedroom with the 3 beds was a great spot for the kids to retreat to for late night movies and playing pool! The kitchen was well appointed with all necessary supplies. The living room couches were so unbelievably comfortable—many naps were taken there. The golf cart was extremely helpful since the beach was a little less than a mile away and the kids did not want to do the walk every day with all the beach stuff. I think our only wishes were that the golf cart was a 6 person and that there was at least another frying pan. Otherwise, amazing trip at an amazing house!

The Dune Den! Huge Yard/Firepit/Near Town+Dunes
This was ur second stay at Andrew’s and it didn’t disappoint. He worked with us last minute to make a reservation so we had somewhere to stay. A friend of ours passed away and we didn’t have a lot of planning time. We love that the place has a pack n play, high chair, and some kids toys & dishes. Things like that make a stay with children much smoother. Thanks again for another great experience.

Designer's Own Cozy Cottage
This place is small yet quaint! Looks like new construction, very updated, and comfy. Even a cute private patio just for us! The bathroom was large, expensive appliances in kitchen, and comfortable king size bed. It was perfect for the two of us!
Quick stats about holiday rentals that are pet-friendly in Grand Beach
Total rentals
10 properties
Total number of reviews
530 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Warren Dunes State Park
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- University of Notre Dame
- The Field Museum
- Lincoln Park
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Washington Park Zoo
- Potato Creek State Park
- The 606
- The Beverly Country Club
- Flossmoor Golf Club
- Chicago Cultural Center