
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.

Amazing Views & Rooftop Deck - Safe - Parking Incl
PRIVATE ROOF DECK SAFE NEIGHBORHOOD PRIVATE PARKING ****30 Minutes to Time Square/Rockefeller Center**** Kick back and relax in this calm, stylish space. **** 3 Positive reviews are required to book this unit **** Enjoy the panoramic city views while having a BBQ or get some work done in the dedicated office area. A perfect getaway for a couple or a small family. Latest check in available is 10 pm, anything after that is subject to a $50-$100 late check in fee subject to availability.

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.

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.

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.

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.

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.

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.

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.

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.
Popular amenities for Fire Island guesthouse rentals
Family-friendly guest house rentals

Private guesthouse

Historic 1 bedroom home in Cold Spring, NY

The Barn by the Sound

Southold- Adorable 1 Bedroom Cottage

Private Studio w/Full Kitchen & Bath

Cozy in laws suite in the woods

Tennis & Sea Escape - Hydrangeas in the Hamptons

Modern+bright forest escape - near village & train
Guest house rentals with a patio

White Cedar Cottage

The Creekside Cottage

Home away from home

The Private Guest House -Lake Ronkonkoma!

Guilford Lakes Cottage, with hot tub and fire pit.

Waterfront Getaway - Norwalk, CT

The Perch, a luxe cottage in the woods 1h from NYC

New Haven Pizza Cozy Guest House 1 mile to yale
Guest house rentals with a washer and dryer

Fully Renovated, Ocean Views, Fireplace & Beach

Chic Coastal Retreat: Modern Apt Steps from Beach

Your Modern Guest Wing Near NYC

Entire Guest House at Fox Pond Farm.

Modern fully updated 2nd Floor apartment

Super Adorable Cottage + Fire pit + King Bed!
Tiny Home in Prime Spot in Southampton Village

A Bright Spot In Brooklyn
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 G$18,824 GYD 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
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- Fitness-friendly rentals Fire Island
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- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Columbia University
- Yale University
- Central Park Zoo
- MetLife Stadium
- Jones Beach
- Yankee Stadium
- Fairfield Beach
- Citi Field
- United Nations Headquarters
- Empire State Building
- Southampton Beach
- Grand Central Terminal
- Statue of Liberty
- Rye Beach
- Cooper's Beach, Southampton
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Canarsie Beach
- The Metropolitan Museum of Art
- Gilgo Beach




