Holiday rentals in Roslyn

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Top-rated holiday rentals in Roslyn

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Fairfield

5 out of 5 average rating, 8 reviews

Newly built twin beach house within steps to beach

Keep it simple at this peaceful and centrally-located home. Newly built in 2019! Premier beach living at its finest. Steps to Fairfield’s beaches and less than a mile to downtown restaurants, shops, and bars. Fenced backyard. Central air throughout. Decks off the front and back with a Weber grill. Furnished with luxury furniture, sheets, comforters, and pillows. Smart TVs in every bedroom and living room. Tesla charging station at the house. Identical home next door available for larger bookings

Superhost

Guest house in Milford

4.92 out of 5 average rating, 205 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Top guest favourite

Home in Northport

4.94 out of 5 average rating, 114 reviews

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

Superhost

Home in Baldwin

4.85 out of 5 average rating, 133 reviews

Clarissa's Paradise

RESERVE NOW: This ideally located five-bedroom totally renovated home is the perfect spot for a family fun vacation. Located within walking distance of the well known playground and spray ground. The home features a spacious patio, central air conditioning, baseboard heating, WiFi, and Cable tv. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. 4 full bathrooms . Sleeps 10. PLEASE NO PARTIES ARE STRICKLY PROHIBITED

Top guest favourite

Home in Ocean Beach

5 out of 5 average rating, 43 reviews

Sunny Spacious Pet Friendly Steps from the Beach

This ideally located four-bedroom home is the perfect spot for your family's vacation. The home features a spacious deck, central air conditioning, WiFi, 4 Smart TV's, a Sonos sound system and YouTube TV. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. There are 2 full bathrooms as well as an outdoor shower. Fully equipped including beach chairs, towels, 5 bikes, 2 wagons and beach toys for the kids. Sleeps 10.

Guest favourite

Home in Milford

5 out of 5 average rating, 5 reviews

Seaside Paradise

Welcome to our beach house in Milford! This getaway is just a short walk from the beach, making it the perfect vacation spot for families or groups of friends. Whether you're looking to soak up the sun on the sandy shores, explore the charming town of Milford, or simply relax in a comfortable beach house, our rental is the perfect choice. We can't wait to host you and make your beach vacation unforgettable. Book now and start counting down the days until your beachside getaway!

Top guest favourite

Home in Milford

5 out of 5 average rating, 101 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Top guest favourite

Cottage in Sea Bright

4.95 out of 5 average rating, 132 reviews

Pineapple Cottage 1 Block to beach sleeps 6!

RARE Off Street Parking for 4 compact cars or 3 SUVs This 3 bedroom beach cottage is a perfect, cost effective alternative to a hotel stay. Wifi, N64, HBO, Cable & board games for those rainy days. Fully furnished bedrooms, one bedroom has home office desk set up, living area, and kitchen, to our comfortable lounge area, BBQ, and outdoor shower. Perfect way to relax after a fun day at a beach, event, or exploring the beautiful town of SeaBright!

Top guest favourite

Flat in Long Beach

4.99 out of 5 average rating, 174 reviews

Incredible Long Beach Private Rental

True 5 star two bedroom rental. Newly renovated and professionally designed. Stunning ocean views from private second floor deck. You have your own barbecue and fully furnished outdoor space so you can enjoy the your stay on your terms. You are just a walk to the bars and restaurants of the West End. No car required! Walk or catch the bus from the train. Only 700 feet from the ocean. Due to allergies in the home we are unable to host any animals.

Guest favourite

Home in Milford

4.91 out of 5 average rating, 57 reviews

Modern Beach Getaway

This 4 bedroom, 3 bathroom vacation rental in Milford, CT, boasts beautiful hardwood floors, high ceilings, and an open-concept living area perfect for entertaining guests. Each bedroom is tastefully decorated, and the fenced-in private yard features a deck and firepit area. The rental is located across the street from a private beach and is a short drive from local shops and restaurants, making it the ideal spot for a summer getaway.

Guest favourite

Flat in Shippan Point

4.93 out of 5 average rating, 84 reviews

Seabreeze at the beach, west beach stamford, Ct

3 bedroom at the beach, free parking also free access to the beach, a cart with chairs, towels, and umbrella. and three adult bicycles, and boogie boards paddle boards. close to downtown and Harbor point, great for people coming to work in Stamford very close to all businesses. EV charging station. about 5 minutes to route 95. also a nice little Irish pub as you enter the beach. "GREAT FOOD AND DRINKS"

Superhost

Bungalow in Highlands

4.79 out of 5 average rating, 98 reviews

Little Haven (B)

A beautiful set of bungalows built in 1903 overlooking Sandy Hook and Manhattan on a private beach. Boat mooring space available. Unit B (beach): second floor, Fully furnished, kitchen fully equipped. 3 bedrooms, 1 bath, full kitchen, no living room. Your living room is the beach outdoors. Beach backyard, gas grills, firepit, and more.