
Guest house holiday rentals in Fire Island
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Top-rated guest house rentals in Fire Island
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Get Back to Nature at a Modern Wood Clad Getaway
WINTER IS HERE…Come and enjoy a wonderful cozy time in our guest house. The winter birds are easy to see and you can still hike along the ocean. Hawks, cardinals, blue jays, bluebirds, gold finches and more are here year round. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Great restaurants along the shore. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Detached bungalow w/ private bath
Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

Modern fully updated 2nd Floor apartment
Arrive to an apartment decorated to make you feel comfortable and at home. There is one bedroom with one queen bed, a dresser, a night table and a closet. One full bath with basic amenities for you. The kitchen has a microwave, blender, coffee machine, toaster, fridge, washer/dryer, full range electrical stove, dinnerware, silverware, glassware, pots, liquid dish soap and sponge. Living/dining room area: dining set for 4; queen sofa bed, Cable TV and closet. Wifi is available! no pets policy!

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 Sunshine House
Enjoy your stay and visit the Bayard Cutting Arboretum, SUSA Orlin & Cohen Sports Complex, Robert Moses Beach; centrally located between The Hamptons Vineyard Wine Tours & Manhattan. This unique home was originally built in 1921 and has since undergone renovations with additions added to the original structure, including the three bedroom / bath guest wing with a private entrance from the main house. We provide beverages and continental breakfast. Please email us for more details!

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.

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.

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!

Private Guest Studio
Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.

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.

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
A unique private and quiet 2 bedroom (1 double bed, two single full beds) totally self contained apt,with sitting room, bathroom ,mud room and full eat in kitchen, in Shaker Hollow, a classic 1795 colonial.Stone patio overlooking 3 1/2 acres of garden and a meadow along with a large fire pit.
Popular amenities for guest house rentals in Fire Island
Family-friendly guest house rentals

A Little House by the sea

Fully Renovated, Ocean Views, Fireplace & Beach

The Hide-A-Way

Adorable 1-Bedroom Guest Cottage in Rowayton

The Rising Tide Cottage

Adorable 1 bedroom beachside cottage

Beautiful Cottage in Greenwich CT

Serenity Haven: A Modern Retreat
Guest house rentals with a patio

The Ultimate Family & Friends Home

Quaint One-Bedroom Cottage with Private Entry

Romantic studio cottage; Walk to town

2 BR Private Suite w/Private Living Room & Kitchen

Cozy 2 BR guest suite very close to JFK, UBS Arena

Home away from home

Waterfront Getaway - Norwalk, CT

Quiet Family Guest Suite
Guest house rentals with a washing machine and dryer

White Cedar Cottage

Beautiful guesthouse - Larchmont

Pound Ridge Cottage

Carriage house flat near beach

Serene Stay Guest House

The Creekside Cottage

Peaceful cottage

The Perch, a luxe cottage in the woods 1h from NYC
Quick stats about guest house rentals in Fire Island

Total holiday rentals
Explore 30 holiday rentals in Fire Island

Nightly prices starting at
Fire Island holiday rentals start at £66 per night before taxes and fees

Verified guest reviews
Over 1,260 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Fire Island holiday rentals include wifi 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
- Plainview Holiday rentals
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- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- Grand Central Terminal
- New York Public Library Main Branch
- Brooklyn Bridge
- New York University
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Yale University
- Old Glory Park
- Ohel Chabad-Lubavitch
- Bronx Zoo
- Yankee Stadium
- Manhattan Bridge
- Jones Beach
- United Nations Headquarters
- Empire State Building
- Citi Field
- Statue of Liberty
- Radio City Music Hall
- Fairfield Beach




