Thimble Islands island rentals
Book unique islands, vacation rentals, and more on Airbnb
Top-rated island rentals in Thimble Islands
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Island in East Hampton
An Island for Rent for Up To 39 People
A Private Island for Rent It's all Lakefront Laurel Island is a five acre Island on a lake in Connecticut. Laurel Island is a perfect location to hold a retreat, reunion, or family group that combines the privacy and peacefulness of an Island and facilities for groups both large and small. Accoommodations include 5 private cottages and a large main Lodge for gathering. Local catering is available for group meals . The five acre Island has canopy trees, blueberry bushes, rocky outcrops
May 7 – 14
Island in East Hampton
Private Island on a Lake Sleeps 39
This private Island is available to rent. You can rent the entire Island or just a cabin or two. We take you to the Island on our pontoon boat and while on the Island you can share the use of our canoes, kayaks, standup boards or paddle boats. There is also volleyball, badminton, horseshoes on the Island. There are five cabins and a Lodge that can be rented together or separately.
Oct 3 – 10
Island in Westport
Island House on Mill Pond
Spend the night in the island house at the center of sherwood mill pond in Westport.
Sep 19 – 26
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Thimble Islands vacation rentals
Thimble Islands vacation rentals
Home in Branford
4.91 out of 5 average rating, 361 reviewsAdorable Beach House on the Long Island Sound
May 5 – 10
Guesthouse in Guilford
4.99 out of 5 average rating, 451 reviewsGet Back to Nature at a Modern Wood Clad Getaway
Aug 19 – 26
Home in East Haven
4.88 out of 5 average rating, 195 reviewsBeach Cottage by the Sea
Mar 16 – 23
Guest suite in Wallingford
5.0 out of 5 average rating, 495 reviewsWintergreen Gardens Suite @ William Becroft House
Jan 18 – 25
Cottage in Clinton
4.87 out of 5 average rating, 391 reviewsShalom Cottage with beach rights.
Mar 12 – 19
Guesthouse in New Haven
4.94 out of 5 average rating, 237 reviewsSquare 6ix
May 10 – 17
Apartment in Milford
4.97 out of 5 average rating, 505 reviewsWater front studio apartment with fireplace.
Aug 27 – Sep 3
Apartment in New Haven
4.89 out of 5 average rating, 465 reviewsFair Haven Heights Entire 1 Bedroom Apartment
Sep 19 – 26
Cottage in Riverhead
4.98 out of 5 average rating, 126 reviewsSavor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Mar 26 – Apr 2
Apartment in West Haven
4.9 out of 5 average rating, 412 reviews! ! ! entire apartment close to the beach ! !
Dec 9 – 16
Apartment in Brookfield
4.94 out of 5 average rating, 179 reviewsPeaceful apartment on 3.5 acres w/ Artist studio.
Nov 29 – Dec 6
Cottage in Guilford
4.96 out of 5 average rating, 157 reviewsLuxury cottage by the sea with hot tub and pool
Feb 11 – 18
Thimble Islands house rentals
Home in Branford
4.88 out of 5 average rating, 176 reviewsGorgeous 4BR Beach House - 250 ft to private beach
Feb 12 – 19
Home in Stony Brook
4.94 out of 5 average rating, 478 reviewsSpacious Studio Apartment- near SBU
Sep 30 – Oct 7
Home in New Haven
4.99 out of 5 average rating, 179 reviewsQ River House - 2 bdrm, minutes from Yale/Downtown
Dec 11 – 18
Home in Holbrook
4.91 out of 5 average rating, 232 reviewsCozy studio
Apr 12 – 19
Home in Centerport
4.95 out of 5 average rating, 111 reviewsThe Harbor House: Beachfront Home 1 hour from NYC
Jul 14 – 21
Home in Preston
4.96 out of 5 average rating, 595 reviewsEntire House Magical Waterfront Getaway
Dec 29 – Jan 5
Home in North Haven
5.0 out of 5 average rating, 122 reviewsLuxury Stay in Expansive Historical Home
Dec 7 – 14
Home in Milford
4.98 out of 5 average rating, 147 reviewsDesigner Beach Retreat on Exclusive Cedar Beach
Nov 21 – 28
Home in Wilton
4.94 out of 5 average rating, 158 reviewsMid Century Modern Cottage
Dec 13 – 20
Home in Lyme
4.97 out of 5 average rating, 185 reviews“The Answer” Tidal River-Kayaks Fire pit Fireplace
Sep 28 – Oct 5
Home in New Haven
4.97 out of 5 average rating, 117 reviewsLI Sound waterview! Take Wedding pics, Yale&Beach
Sep 24 – Oct 1
Home in Port Jefferson
4.95 out of 5 average rating, 133 reviewsThe Hidden Retreat ~ Family friendly Walk to Beach
Apr 8 – 15
Other great vacation rentals in Thimble Islands
Guest suite in Morris
4.99 out of 5 average rating, 340 reviewsLakeside Private Guest Suite
Feb 19 – 26
Apartment in New Haven
4.97 out of 5 average rating, 202 reviewsThe Pearl, New Haven
Aug 23 – 30
Tiny home in Guilford
4.94 out of 5 average rating, 202 reviewsStay in a Tiny House on a Small Sustainable Farm
Jul 28 – Aug 4
Guest suite in Cutchogue
4.88 out of 5 average rating, 582 reviewsWalk to Vineyards, Beaches, Farms & Town
Aug 27 – Sep 3
Apartment in Middletown
4.99 out of 5 average rating, 140 reviewsApartment Near Wesleyan, Downtown, Wedding Venues!
Aug 17 – 24
Cottage in Branford
4.86 out of 5 average rating, 195 reviewsCozy Home In Short Beach Community
Nov 4 – 11
Apartment in East Haddam
4.89 out of 5 average rating, 102 reviewsPenny Corner Airbnb
Jan 8 – 15
Cottage in Guilford
5.0 out of 5 average rating, 80 reviewsWaterfront Joshua Cove Cottage with private beach.
Dec 8 – 15
Guesthouse in Branford
4.79 out of 5 average rating, 47 reviewsStudio on the shore - Short Beach - Water Views
Sep 24 – Oct 1
Cottage in Guilford
5.0 out of 5 average rating, 15 reviewsWaterfront Cottage With Unforgettable Views
Feb 4 – 11
Cottage in Guilford
4.88 out of 5 average rating, 8 reviewsYour own Thimble Islands private cottage!
Aug 13 – 20
Vacation home in Guilford
4.98 out of 5 average rating, 59 reviewsSpacious Oceanfront Getaway with Spectacular Views
Feb 3 – 10
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Newark Vacation rentals
- Montauk Vacation rentals
- Hoboken Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom