Guesthouse vacation rentals in Fire Island

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Top-rated guesthouse rentals in Fire Island

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

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Top guest favorite
A private outdoor space is showcased with a wooden deck, featuring two lounge chairs and a dining table shaded by an umbrella. Potted flowers add color, while a path leads through the well-maintained garden, enhancing the serene atmosphere of the yard.
Guesthouse in The Hamptons
4.97 out of 5 average rating, 209 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.

Top guest favorite
A modest wooden house features large glass doors that lead to a spacious deck. The surrounding green lawn is complemented by well-kept shrubs and trees. Sunlight casts a warm glow on the exterior, highlighting the structure's simple charm.
Guesthouse in Rowayton
4.99 out of 5 average rating, 151 reviews

1BR full cottage, 1 min walk to private beach

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian and dog friendly town; you don't even need a car while here.

Guest favorite
The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.
Guesthouse in Waccabuc
4.98 out of 5 average rating, 117 reviews

French Guest House in Waccabuc

A mini Versailles just outside of NYC - located on a private and gated eight acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s equivalent to staying in a 5-Star European luxury hotel suite (house designed by David Easton) with its heated stone floors and heated towel rack, luxury linens, gold taps and serene private entrance. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train St)

Guest favorite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guesthouse in Pound Ridge
4.94 out of 5 average rating, 100 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Guest favorite
A spacious bedroom features a large bed with neutral bedding, complemented by a comfortable, modern seating area. Natural light fills the room through multiple windows, and built-in shelves showcase books and decorative items, adding functionality and style to the space.
Guesthouse in Mamaroneck
4.9 out of 5 average rating, 166 reviews

Your Modern Guest Wing Near NYC

Brand New Guest Wing in an exclusive private home with a separate entrance. One large bedroom, kitchenette, master bathroom, closet space & separate laundry closet. Steam shower with special steam light function and aroma therapy. High End Kitchenette. 4 minute drive to Mamaroneck train station. 35 minute train and/or drive to Grand Central (Manhattan). Close to the Village of Mamaroneck Avenue center. High speed internet. Outdoor CCTV.

Guest favorite
A cozy living area features mid-century modern furniture, including an orange armchair and a sleek glass coffee table. A gallery wall displays various artworks, complemented by natural light from two windows. A small dining area with a round table and four chairs contributes to the inviting layout.
Guesthouse in Westville
4.92 out of 5 average rating, 329 reviews

Square 6ix

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.

Top guest favorite
A spiral staircase with a sleek black railing leads to the loft bedroom. A mirror with a burgundy frame is mounted against the wall, reflecting the light. The open living area features a light-colored couch and a wooden dining table, visible through large windows offering views of the outdoors.
Guesthouse in Mystic
4.98 out of 5 average rating, 660 reviews

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Guest favorite
A bright sleeping area features a spacious bed with light bedding, positioned beneath a vaulted ceiling. Floor-to-ceiling windows provide views of the woods, while a small desk and chair are set against one wall for workspace. A television is mounted for entertainment.
Guesthouse in Greenwich
4.95 out of 5 average rating, 105 reviews

The Cottage in Greenwich

Brand new, light-filled private cottage guesthouse overlooking the woods in the heart of Greenwich, CT. Floor to ceiling windows, radiant heat bathroom floors, queen Casper mattress, a dedicated parking spot, Wi-Fi, TV, kitchenette with full fridge, Keurig coffee maker, microwave, toaster and induction stovetop and all utensils. Perfect for a weekend getaway or a quiet place to work.

Guest favorite
The interior space features a cozy living area with a sofa and coffee table, complemented by a vibrant area rug. A brick fireplace is located along one wall, while the kitchen area includes modern appliances and bar seating. Natural light floods through large windows.
Guesthouse in Mystic
4.97 out of 5 average rating, 306 reviews

True Artist Loft, 5 minutes to downtown Mystic

A Historic Artist’s Retreat Near Downtown Mystic Lovingly known as The Dacha for nearly 80 years, this one-of-a-kind gem was built in 1945 as a studio for the artist who once called the property home. Fully insulated for cozy winter stays, the unique structure is tucked away on a peaceful piece of land, just five minutes from downtown Mystic.

Guest favorite
A comfortable living area is featured, showcasing a brown sofa with colorful pillows and a small table. Large windows are adorned with checkered curtains, allowing natural light to fill the room. A light fixture hangs above a blue cabinet, adding a touch of charm.
Guesthouse in Sayville
4.96 out of 5 average rating, 215 reviews

Great South Bay Cottage

Fantastic private cottage on Long Island's South Shore. Great access to the best beaches in the world (walk to bay, ferries to ocean). Short train ride to/from NYC, Wineries & The Hampton's. Experience the Island’s charm and culture. Enjoy Long Island summers. We employ a professional cleaning regiment.

Top guest favorite
Guesthouse in Southport
4.97 out of 5 average rating, 204 reviews

Southport, CT across from BEACH

Located at Southport beach on Westport Line, this renovated 1 bedroom apartment totally private located above the garage and includes a full kitchen with new appliance and d/w and central air. Bdrm with queen, fine cotton sheets and towels, marble bath open living room w views.

Guest favorite
A private brick patio is depicted, featuring a round table with four white plastic chairs beneath a floral umbrella. Potted plants adorn the space, and a striped chair is positioned nearby, creating an inviting outdoor setting.
Guesthouse in East Meadow
4.93 out of 5 average rating, 168 reviews

Petite Cottage

Petite Cottage is quiet yet convenient to beautiful Long Island Beaches, North Fork Vineyards, South Fork, The Hampton's and fine eateries. Close to the excitement of Manhattan's Broadway Shows, Fine Dining, Central Park, Museums and Galleries.

Popular amenities for Fire Island guesthouse rentals

Quick stats about guesthouse rentals in Fire Island

  • Total vacation rentals

    Explore 30 vacation rentals in Fire Island

  • Nightly prices starting at

    Fire Island vacation rentals start at R1,559 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 1,260 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Fire Island vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Fire Island rentals

  • 4.9 Average rating

    Fire Island stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Fire Island's top spots, include Fire Island National Seashore, Islip Cinemas, and Plaza Cinema & Media Arts Center

Destinations to explore