Holiday rentals in Thimble Island

New Spacious Home in Boston

Welcome to our spacious urban retreat in the heart of Boston. This well maintained 4 bedroom unit is conveniently located near many city attractions. Enjoy quiet patio, backyard and free coffee bar. Great for a quick getaway or special gathering. 5 min walk to access bus and train 10 min drive to UMass Boston and JFK Library 20 min drive to Fenway Park and TD garden sports 10 min drive to the famous Franklin Park Zoo/Golf Course 20 min drive to Historical Downtown Boston and Prudential Shopping

Value · Location · Amenities

Top guest favourite

Guest favourite

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!

Value · Family · Air conditioning

🎖The Ashmont Suite | Close to Subway + Downtown🎖

This high end & unique 3 bed / 2 bath unit is brand new, along with all the furnishings. It includes 1 King, 1 Double, & 1 Single size private bedrooms. The unit is extremely clean and remarkably decorated. Only a 5 minute walk to Ashmont station (red line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. There’s also plenty of parking available in front of the property. As well as a local coffee shop & a Dunkin just across Ashmont T station.

Location · Family · Kitchen

Timeless Stay | Freedom Trail. Fitness Center

Explore a beautifully reimagined luxury hotel, The Newbury Boston, where the bustle of the Back Bay is your playground and the idyllic Boston Public Garden your front yard. Attractions just nearby: ✔Boston Expressionist paintings and Chinese ceramics at Museum of Fine Arts ✔Deep dive into history at Boston’s Tea Party Museum ✔Sharks, rays, penguins at New England Aquarium ✔400 years of Boston’s history and the story of nation’s pursuit of liberty, Freedom Trail ✔Downtown Boston

Family · Value · Bathroom

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Guest favourite

219 on the Ocean with Private Bath

An old Boston home in Savin Hill. My place is close to The T, overlooks Malibu and Savin Hill Beaches, easy to get here from the airport, and easy to get downtown. We are close to restaurants, the JFK Museum, and the Harbor-walk. You’ll love my place because of the quiet and beauty. You will have your solitude and privacy. My place is good for solo adventurers, business travelers, medical people. All walks of life welcomed here. Registered with the City of Boston #STR383505

Family · Value · Laundry

Seaport Hotel® Boston, Deluxe room king bed

Deluxe room one king bed features a king bed with a pillowtop mattress, local artwork, and city or Boston Harbor views. Enjoy a 55-inch HDTV, complimentary wifi, Keurig coffee maker, mini refrigerator, laptop-sized safe, and a beautifully appointed bathroom with Gilchrist and Soames BeeKind toiletries, fog free mirror, and walk-in shower or tub. Additional amenities include complimentary bottled water, rolling desk, Tivoli audio system, and access to the Wall Street Journal.

Value · Location · Condition

Top guest favourite

Guest favourite

4br SouthBoston free parkg nrBeach, 6 min>BCEC

Bring the whole family or team -- you'll love our quiet, safe, beachside neighborhood. Our location on the South Boston peninsula means more peace and less traffic, yet a short scenic walk up K Street brings you to great restaurants. <5min walk to a great grocery store, the legendary L St Tavern and L St Bathhouse. <1.5 mi to Convention Center & Seaport. 3 BRs w queen beds and 1 sm BR w bunks, large kitchen, liv & dining rooms, & bonus sunroom w/desk. Call us today -- we'd

Location · Value · Parking

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.

Value · Family · Accuracy

Top guest favourite

Guest favourite

Bright Near Boston, Airport & Beach | Free Parking

Enjoy a spacious and peaceful room just a 2-minute walk from the beach. A variety of restaurants, supermarkets, banks, and other conveniences are just a few minutes away. Relax in a comfortable queen bed, work at the dedicated desk, and enjoy the quiet neighborhood. Just a 14-minute walk to the MBTA Red Line, with easy access to Downtown Boston. Perfect for business or leisure stays.

Location · Value · Parking

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.

Value · Family · Access

enVision Hotel Boston - Everett, Boutique room ki.

Boutique room king bed features a plush king bed, a button tufted lounge chair, and a luggage bench for a touch of luxury. Enjoy a hospitality center with fridge, flat screen tv, single cup keurig coffee maker, and convenient wifi. The reclaimed wood work desk and comfortable desk chair create a unique and inviting atmosphere for both relaxation and productivity.

Location · Family · Access

Top guest favourite

Guest favourite

Light-Filled Luxury Apartment with View

Beautiful top floor luxury apartment in stately Victorian home. Extraordinary views of historic park as your front yard! Your own entrance through a private garden. Apartment is a studio-style open living space with full kitchen, living area, and bedroom bay with queen bed. Also includes loft bedroom with 2 twin beds.

Value · Location · Air conditioning