Holiday houses in City Island

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Top-rated holiday rentals in City Island

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Guest favourite
A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.
Home in Rye
4.91 out of 5 average rating, 144 reviews

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

Top Guest favourite
A cozy living room features a large flat-screen TV mounted on the wall, accompanied by a sleek entertainment unit. A comfortable couch is draped with a soft blanket, and an armchair is positioned nearby. Natural light enters through two windows, brightening the neutral decor.
Guesthouse in Mamaroneck
4.97 out of 5 average rating, 113 reviews

Spacious guest suite near water

Welcome to your perfect home away from home! Enjoy a spacious and newly renovated basement suite with windows and separate entrance in a private house, perfect for up to four guests. Ideal for couples, small families, or business travelers. This cozy retreat, combines privacy and comfort in a quiet neighborhood. Whether you’re here for a short trip or an extended stay, this apartment offers everything you need for a comfortable and relaxing experience. Book now and start planning your visit.

Top Guest favourite
Home in Greenwood Lake
5.0 out of 5 average rating, 220 reviews

Panoramic Lakeviews & Lush Garden | Beach Access

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features hundreds of plants and a seasonal waterfall cascading into a lily pond with fish and frogs. A shaded patio offers panoramic views and a gas grill. Guests get access to a private community beach. In winter, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy living room, with exposed wooden ceilings, fireplace, smart TV, record player and board games.

Guest favourite
An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.
Cottage in Greenwood Lake
4.97 out of 5 average rating, 387 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Guest favourite
Home in Centerport
4.95 out of 5 average rating, 176 reviews

The Harbor House: Beachfront Home 1 hour from NYC

FEATURED #1 on Refinery29's "11 Best Beach Houses Near NYC" Welcome to Long Island’s iconic Gold Coast! Wake up to sweeping waterfront views and, if you’re lucky, catch a glimpse of our local bald eagle family soaring overhead! Explore nearby gems like the Vanderbilt Mansion & Planetarium, Caumsett State Historic Park Preserve, Del Vino Vineyards, and the lively Paramount Theatre. Stroll through Downtown Huntington or Northport Village for boutique shopping, great restaurants.

Guest favourite
Home in Greenwich
4.97 out of 5 average rating, 68 reviews

Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC

Once home to actress Misty Rowe (Hee Haw, Brady Bunch, Love Boat), this historic riverside cottage blends rustic charm with modern luxury. Cozy up by the stone fireplace, cook in the chef's kitchen, or unwind on the river-facing deck. Splash in the heated pool, soak in the year-round hot tub, gather by the gazebo, or spot wildlife along the water. Two fire pits, river views, and pure tranquility — just 5 min to downtown Greenwich and 35 min to NYC. Your riverside escape awaits.

Guest favourite
Apartment in Yonkers
4.94 out of 5 average rating, 117 reviews

Modern 2BR Sleeps 6 | Free Parking | Near Metro

Welcome to our charming 2 bedroom apartment nestled in the heart of Yonkers, NY! This cozy haven boasts modern amenities and a serene ambiance, providing the perfect blend of comfort and convenience. Escape the hustle and bustle of the city while still being within easy reach. Experience the best of both worlds by residing in our suburban oasis with the exhilarating NYC just a stone's throw away. Book your stay today and make unforgettable memories in our home away from

Top Guest favourite
A two-story house features a modern design with gray siding and large windows. Soft outdoor lighting illuminates the exterior, highlighting the entryway with stone steps and an iron gate adorned with lush green plants and red flowers, creating a welcoming appearance.
Home in City Island
4.98 out of 5 average rating, 121 reviews

Large NYC Home! Close Proximity to Manhattan!

Have fun at this stylish place. You will enjoy a large backyard with patio, fire pit, deck, ping pong table and gas BBQ. The house has plenty of space and is in the center of town and walking distance to the beach and restaurants and 20 minutes to Manhattan. Enjoy this hidden gem of a neighborhood- City Island, the seaport of the Bronx! The basement is set up as a 2 bedroom space for additional use and privacy if needed at an additional charge!

Top Guest favourite
The lakeside property features a well-manicured lawn leading to the water's edge, complemented by a dock and a single kayak. Lounge chairs are arranged near a shaded gazebo, with a stone pathway guiding guests towards the house, which is framed by lush greenery.
Home in Greenwood Lake
4.97 out of 5 average rating, 110 reviews

Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC

Escape to our modern, year-round lakeside paradise on Greenwood Lake, just 1 hour from NYC. This bright, airy home offers stunning lake views, a private dock, and a sandy beach area. Perfect for families or couples, enjoy seasonal activities from swimming and kayaking in the summer to skiing just 10 minutes away in the winter. Relax by one of two fireplaces or on the spacious deck. A tranquil retreat for relaxation and adventure. Permit N. 23-225

Top Guest favourite
A detached studio with a charming exterior is surrounded by lush greenery and landscaped gardens. The structure features large windows framed in dark trim, allowing natural light to fill the interior. A stone pathway leads up to the entrance, enhancing the inviting appearance of the property.
Guesthouse in Larchmont Village
4.99 out of 5 average rating, 71 reviews

Beautiful guesthouse - Larchmont

Newly furnished 2nd floor detached studio with private entrance.  One large bedroom with queen-size bed, full bath with spacious shower, kitchenette, and armoire.  Lots of light and beautiful views overlooking luscious landscaping and the surrounding quiet Rouken Glen neighborhood.  Studio sits over garage.  Access to spare washer/dryer in our basement is also available.  4 min drive to Larchmont station (35 min train to Grand Central).

Top Guest favourite
Home in Riverdale
4.99 out of 5 average rating, 69 reviews

Stylish Guest Suite in The Heart of NYC

Experience luxury in the upscale Riverdale neighborhood in our spacious, sunlit guest suite. It features a beautifully designed private bathroom and a fully equipped kitchen. The queen-sized bed and dedicated workspace create an ideal setting for relaxing and unwinding in your perfect city retreat. The house is a charming Dutch Colonial home; the suite is on the second floor with a private entrance via a walk-up staircase.

Top Guest favourite
A spacious bedroom is presented, featuring a sizable bed dressed in soft white linens and accented by numerous decorative pillows. Two lamps provide gentle illumination on either side, while artwork adorns the walls. A wooden bench is positioned at the foot of the bed.
Apartment in New Rochelle
4.99 out of 5 average rating, 197 reviews

Woven Winds Retreat

Looking to escape the city for some much-needed rest and relaxation? Come and enjoy our spacious apartment, featuring two bedrooms, one bathroom, a fully equipped kitchen, and a large living and dining area. Want to spend time outdoors? Step outside to our sizable backyard with an enclosed pavilion with lounging furniture. An added bonus: we're only 10 minutes away from Orchard Beach!

Popular amenities for City Island holiday rentals

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  2. United States
  3. New York
  4. Bronx County
  5. Bronx
  6. City Island