Guesthouse vacation rentals in Fire Island
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Top-rated guesthouses in Fire Island
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Fire Island guesthouses
Family-friendly guesthouses
Guesthouse in Southampton
4.95 out of 5 average rating, 411 reviewsTiny Home in Prime Spot in Southampton Village
Oct. 6 – 13
Guesthouse in South Salem
4.93 out of 5 average rating, 220 reviews1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
Jan. 18 – 25
Guesthouse in Atlantic Highlands
4.87 out of 5 average rating, 303 reviewsPrivate cabin
Aug. 20 – 27
Guesthouse in Asbury Park
4.98 out of 5 average rating, 226 reviewsPeaceful Guesthouse
Dec. 18 – 25
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Jul. 28 – Aug. 4
Guesthouse in Beacon
4.94 out of 5 average rating, 367 reviewsCozy Mountainside Suite - Minutes from Beacon
Dec. 19 – 26
Guesthouse in Jamesport
4.97 out of 5 average rating, 107 reviewsWalk to Beautiful Beach in Heart of Wine Country
Feb. 23 – Mar. 2
Guesthouse in Yonkers
4.76 out of 5 average rating, 104 reviewsSt James Guest House
Sep. 24 – Oct. 1
Guesthouses with a patio
Guesthouse in Shirley
4.97 out of 5 average rating, 34 reviewsLa little house J place
May 13 – 20
Guesthouse in Hempstead
4.86 out of 5 average rating, 80 reviewsPrivate Guest house with pool access.
Apr. 12 – 19
Guesthouse in Newtown
5.0 out of 5 average rating, 44 reviewsFarm Cottage
Oct. 22 – 29
Guesthouse in Massapequa
5.0 out of 5 average rating, 15 reviewsModern Custom Studio: 50 mins to NYC
Aug. 31 – Sep. 7
Guesthouse in Hampton Bays
4.91 out of 5 average rating, 43 reviewsQuaint One Bedroom Cottage with Private Entrance
Nov. 27 – Dec. 4
Guesthouse in Highlands
4.89 out of 5 average rating, 56 reviewsThe Bungalow at Sandy Hook House
Oct. 7 – 14
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
Jul. 13 – 20
Guesthouse in North Castle
4.98 out of 5 average rating, 43 reviewsMagical 1700's 1 bedroom cottage
Jul. 31 – Aug. 7
Guesthouse rentals with a washer and dryer
Guesthouse in Brewster
5.0 out of 5 average rating, 290 reviewsThe Cottage by the Lake: Hudson Valley Indulgence
Aug. 1 – 8
Guesthouse in Stonington
4.99 out of 5 average rating, 188 reviewsSuper Adorable Cottage + Fire pit + King Bed!
Jan. 30 – Feb. 6
Guesthouse in Bedford Hills
4.91 out of 5 average rating, 112 reviewsBarrett's Sanctuary
Aug. 18 – 25
Guesthouse in Mamaroneck
4.94 out of 5 average rating, 127 reviewsYour Modern Guest Wing Near NYC
Aug. 20 – 27
Guesthouse in Madison
5.0 out of 5 average rating, 58 reviewsThe Barn by the Sound
Jan. 28 – Feb. 4
Guesthouse in Cold Spring
4.99 out of 5 average rating, 95 reviewsBright/modern forest escape. Near village & train
Dec. 11 – 18
Guesthouse in Southold
4.95 out of 5 average rating, 40 reviewsSouthold- Adorable 1 Bedroom Cottage
May 7 – 14
Guesthouse in Pound Ridge
4.95 out of 5 average rating, 66 reviewsA Lovely Cottage in the Woods
May 4 – 11
Quick stats about guesthouse rentals in Fire Island
Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Total number of reviews
1K reviews
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