Holiday rentals in Squantum

Spacious 1-Bed Apt. in Peaceful Weymouth W/Balcony

Spacious and sunlit 1-bedroom apartment in a peaceful Weymouth neighborhood, featuring a private balcony and relaxing views.Perfect urban retreat for relaxing or working from home, blending quiet natural beauty with excellent proximity to local seaside parks and easy Boston commuting.Open-concept layout featuring oversized windows that flood the apartment with natural light & connect directly to your private balcony offering quiet, peaceful views, perfect for morning coffee or evening unwinding.

New modern 2bd condo: free parking/near train

This newly renovated, modern unit on the 1st floor of a charming two-family house is situated on a quiet side street in Roslindale. Just under a mile from the commuter rail, only a quick 15-20min ride to downtown Boston. conEasy access to restaurants, shops, and some of Boston’s most stunning parks. The unit boasts a spacious kitchen, two cozy bedrooms, an open living, dining area, and two private entries. It’s the perfect retreat for both urban explorers and those seeking a peaceful getaway.

Extraordinary 1-Bedroom Apartment in South Boston!

Cozy, comfortable, centrally-located one-bedroom unit in Southie. Unbeatable location, steps from Carson Beach, L Street Bathouse, BCEC, Sail Boston, World Cup 2026! This property presents endless possibilities for creating your perfect getaway! Convenient private entrance ensures hassle-free coming and going. Whether commuting to work, enjoying a concert/game/event/the vibrant local scene, or simply indulging in the beach and parks nearby, you are sure to enjoy it at this very special home!

J&K's BnB .... Private studio Airbnb with parking

Our non-smoking private Studio Bnb is located by the airport in Point Shirley; a small safe seaside community. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free 5G wireless WiFi, RokuTV, one car off-street parking. Due to our severe medical health allergies to animal hair, fur & feathers, Airbnb has granted us an exemption not to host guests service or emotional support animals.

Boston Buccaneer Retreat

Modern Luxury Near Forest Hills Station – A Sophisticated Urban Retreat Experience unparalleled elegance in this brand-new, high-end residence, perfectly positioned just moments from Forest Hills Station. Designed for discerning travelers, this exquisite home blends sophisticated design, premium finishes, and state-of-the-art amenities. The Orange Line is just outside the porch . save on rental cars and enjoy a gateway to Northeastern University and all of Boston's top transit routes.

Spacious Beachfront Bliss, trails&walk Marina Bay

Beautiful renovated 2-bedroom apartment directly across from the beach with ocean views and coastal breezes.This is a private second-floor apartment in a two-family home. Spacious, stylish, and located in a quiet family-friendly area, perfect for a getaway. Enjoy scenic running and walking trails, walking distance to Marina Bay for waterfront dining, cafés, and marina views and close to the famous Tony’s Clam Shop. The perfect mix of comfort, location, and beachside charm.

Guest Suite in Milton

This private suite features 2 comfortable bedrooms with cozy bedding. The suite includes a fully equipped kitchenette stocked with essentials for preparing meals. A clean, modern bathroom is supplied with fresh towels and basic toiletries for your convenience. It’s perfect for small families, couples, or business travelers. Enjoy complete privacy with your own separate entrance from the main house, allowing you to come and go as you please without disturbance.

Winthrop Hideaway | Near Airport, Beaches & Boston

Escape to Get to the Point Boston, a cozy private studio in charming Winthrop just minutes from Logan Airport and downtown Boston. Enjoy free off-street parking, high-speed WiFi, premium linens, a Nespresso coffee station, complimentary snacks, and no cleaning fee. Walk to beaches, parks, restaurants, and stunning Boston skyline sunsets. Perfect for couples, business travelers, airline crews, and weekend explorers seeking comfort, convenience, and value.

Your own cottage in the city

Whether you need to relax, be productive, or have a safe home base for your adventures, the Sowden cottage has you covered. Nestled near the heart of Roslindale, the cottage is a short walk to shopping and dining and is near easy transportation to every part of Boston. It's the perfect place to call home while you work, visit family, or experience the city we love. Whatever brings you to Boston, we look forward to welcoming you at the cottage!

Perfectly Renovated Home w/ Private Outdoor Oasis

COMPLETELY PRIVATE - NO SHARED SPACE OTHER THEN WASHER/DRYER AREA IN BASEMENT! Enjoy a private kitchen, 2 bedrooms, 2 baths and private outdoor space. The Master Bedroom has a king Bed with an ensuite bathroom. The Second Bedroom has a queen bed, gas fireplace and is right across from the second full bath. PARKING IS NOT INCLUDED. **outdoor furniture will be put away for the Winter in November & reassembled mid-May*

Bayfront Retreat with Private Ramp &Stunning Views

Make some memories at this unique and family-friendly place. This is a peaceful single family home with a private boat ramp that can also be used as beach access. Beautiful views of the bay and sunrise, the house has 3 bedrooms (sleeps up to 7, or utilize the couch on the sunroom to accommodate more), sunroom, garage, wood burning stove and outdoor seating. NON-smoking property.

Curated Designer Retreat • Pool • Gym • Dining

Experience modern Everett living in this bright 2BR/2BA home! Enjoy a fully equipped kitchen with stainless steel appliances, in-unit laundry, and spacious sunlit living areas. Relax by the courtyard pool, stay active in the 24/7 fitness center, or unwind in the outdoor lounges and fire pits. Close to Encore, Assembly Row and major highways for easy access to Greater Boston.