
Guest house holiday rentals in Fire Island
Find and book unique guest house rentals on Airbnb
Top-rated guest house rentals in Fire Island
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

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.

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.

The Cozy Little Cottage
Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed. We have a twin air mattress for use in the living room.

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)

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.

★Tiny House Cottage 35 min to NYC on Hudson River★
Please read the entire listing to set expectations. Super charming, slightly quirky, never perfect private Shangri-La with backyard chickens in the artistic and quaint Rivertowns, 35 minutes from NYC along the Hudson River. The Tiny House escape is reminiscent of sleepaway camp (Rustic), yet tastefully curated with eclectic art and furnishings. Sleeping loft nest with 8-step ladder or pull-out sofa bed. Fenced-in yard. FREE 24/7 street parking. Read on…

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.

Peekskill Carriage House Downtown Studio
Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

The Unhampton
This Brookhaven Hamlet detached space (totally separate) is for people who love nature and preserved quiet spaces. Fire Island is a ferry ride away, Manhattan is one hour by train and the Hamptons are a 25 minute ride.15 minutes from the restaurants and coffee shops in Patchogue and just a couple of minutes from Bellport Village. Centrally located and truly peaceful!

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.

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.

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 guest house rentals in Fire Island
Family-friendly guest house rentals

Amazing Views & Rooftop Deck - Safe - Parking Incl

A Little House by the sea

The Hide-A-Way

White Cedar Cottage

Gorgeous Waterfront Getaway

Adorable 1 bedroom beachside cottage

Beautiful Cottage in Greenwich CT

True Artist Loft, 5 minutes to downtown Mystic
Guest house rentals with a patio

The Cottage in Greenwich

Private guesthouse

The Creekside Cottage

Home away from home

Guilford Lakes Cottage, with hot tub and fire pit.

Waterfront Getaway - Norwalk, CT

Quiet Family Guest Suite

The Perch, a luxe cottage in the woods 1h from NYC
Guest house rentals with a washing machine and dryer

Fully Renovated, Ocean Views, Fireplace & Beach

Chic Coastal Retreat: Modern Apt Steps from Beach

Cottage by the Sea

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

Your Modern Guest Wing Near NYC

Entire Guest House at Fox Pond Farm.

Modern fully updated 2nd Floor apartment

The Estate Private Guest House -Lake Ronkonkoma!
Quick stats about guest house rentals in Fire Island
Total rentals
30 properties
Nightly prices starting at
£67 before taxes and fees
Total number of reviews
1.3K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Philadelphia Holiday rentals
- Mount Pocono Holiday rentals
- Jersey Shore Holiday rentals
- Ocean City Holiday rentals
- The Hamptons Holiday rentals
- Rentals with beach access Fire Island
- Rentals with lake access Fire Island
- Rentals with a kayak Fire Island
- Waterfront rentals Fire Island
- Fitness-friendly rentals Fire Island
- Flat rentals Fire Island
- Rentals with a fireplace Fire Island
- Hotel rentals Fire Island
- Rentals with a firepit Fire Island
- Cottage rentals Fire Island
- House rentals Fire Island
- Rentals with a hot tub Fire Island
- Family-friendly rentals Fire Island
- Bungalow rentals Fire Island
- Rentals with a patio Fire Island
- Rentals with a washing machine and dryer Fire Island
- Beachfront rentals Fire Island
- Rentals with pools Fire Island
- Apartment rentals Fire Island
- Beach house rentals Fire Island
- Pet-friendly rentals Fire Island
- Rentals with breakfast Fire Island
- Private suite rentals Fire Island
- Rentals with outdoor seating Fire Island
- Smoking-friendly rentals Fire Island
- Guest house rentals Suffolk County
- Guest house rentals New York
- Guest house rentals United States
- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Empire State Building
- Columbia University
- MetLife Stadium
- Yale University
- Jones Beach
- Central Park Zoo
- Yankee Stadium
- Citi Field
- Fairfield Beach
- United Nations Headquarters
- Southampton Beach
- Rye Beach
- Cooper's Beach, Southampton
- Grand Central Terminal
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Canarsie Beach
- Gilgo Beach
- The Metropolitan Museum of Art