Thimble Islands island rentals

Book unique islands, vacation rentals, and more on Airbnb

Popular amenities for Thimble Islands vacation rentals

Thimble Islands vacation rentals

Guest favorite

Home in Branford

4.91 out of 5 average rating, 361 reviews

Adorable Beach House on the Long Island Sound

May 5 – 10

$175 per night
Guest favorite

Guesthouse in Guilford

4.99 out of 5 average rating, 451 reviews

Get Back to Nature at a Modern Wood Clad Getaway

Aug 19 – 26

$254 per night
Superhost

Home in East Haven

4.88 out of 5 average rating, 195 reviews

Beach Cottage by the Sea

Mar 16 – 23

$136 per night
Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 495 reviews

Wintergreen Gardens Suite @ William Becroft House

Jan 18 – 25

$73 per night
Superhost

Cottage in Clinton

4.87 out of 5 average rating, 391 reviews

Shalom Cottage with beach rights.

Mar 12 – 19

$88 per night
Guest favorite

Guesthouse in New Haven

4.94 out of 5 average rating, 237 reviews

Square 6ix

May 10 – 17

$109 per night
Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 505 reviews

Water front studio apartment with fireplace.

Aug 27 – Sep 3

$175 per night
Guest favorite

Apartment in New Haven

4.89 out of 5 average rating, 465 reviews

Fair Haven Heights Entire 1 Bedroom Apartment

Sep 19 – 26

$99 per night
Guest favorite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Mar 26 – Apr 2

$650 per night
Guest favorite

Apartment in West Haven

4.9 out of 5 average rating, 412 reviews

! ! ! entire apartment close to the beach ! !

Dec 9 – 16

$98 per night
Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 179 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Nov 29 – Dec 6

$110 per night
Guest favorite

Cottage in Guilford

4.96 out of 5 average rating, 157 reviews

Luxury cottage by the sea with hot tub and pool

Feb 11 – 18

$293 per night

Thimble Islands house rentals

Guest favorite

Home in Branford

4.88 out of 5 average rating, 176 reviews

Gorgeous 4BR Beach House - 250 ft to private beach

Feb 12 – 19

$259 per night
Guest favorite

Home in Stony Brook

4.94 out of 5 average rating, 478 reviews

Spacious Studio Apartment- near SBU

Sep 30 – Oct 7

$90 per night
Guest favorite

Home in New Haven

4.99 out of 5 average rating, 179 reviews

Q River House - 2 bdrm, minutes from Yale/Downtown

Dec 11 – 18

$157 per night
Guest favorite

Home in Holbrook

4.91 out of 5 average rating, 232 reviews

Cozy studio

Apr 12 – 19

$87 per night
Guest favorite

Home in Centerport

4.95 out of 5 average rating, 111 reviews

The Harbor House: Beachfront Home 1 hour from NYC

Jul 14 – 21

$679 per night
Guest favorite

Home in Preston

4.96 out of 5 average rating, 595 reviews

Entire House Magical Waterfront Getaway

Dec 29 – Jan 5

$160 per night
Guest favorite

Home in North Haven

5.0 out of 5 average rating, 122 reviews

Luxury Stay in Expansive Historical Home

Dec 7 – 14

$854 per night
Guest favorite

Home in Milford

4.98 out of 5 average rating, 147 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Nov 21 – 28

$302 per night
Guest favorite

Home in Wilton

4.94 out of 5 average rating, 158 reviews

Mid Century Modern Cottage

Dec 13 – 20

$121 per night
Guest favorite

Home in Lyme

4.97 out of 5 average rating, 185 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

Sep 28 – Oct 5

$296 per night
Guest favorite

Home in New Haven

4.97 out of 5 average rating, 117 reviews

LI Sound waterview! Take Wedding pics, Yale&Beach

Sep 24 – Oct 1

$533 per night
Superhost

Home in Port Jefferson

4.95 out of 5 average rating, 133 reviews

The Hidden Retreat ~ Family friendly Walk to Beach

Apr 8 – 15

$387 per night

Other great vacation rentals in Thimble Islands

Guest favorite

Guest suite in Morris

4.99 out of 5 average rating, 340 reviews

Lakeside Private Guest Suite

Feb 19 – 26

$82 per night
Guest favorite

Apartment in New Haven

4.97 out of 5 average rating, 202 reviews

The Pearl, New Haven

Aug 23 – 30

$140 per night
Guest favorite

Tiny home in Guilford

4.94 out of 5 average rating, 202 reviews

Stay in a Tiny House on a Small Sustainable Farm

Jul 28 – Aug 4

$155 per night
Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 582 reviews

Walk to Vineyards, Beaches, Farms & Town

Aug 27 – Sep 3

$141 per night
Guest favorite

Apartment in Middletown

4.99 out of 5 average rating, 140 reviews

Apartment Near Wesleyan, Downtown, Wedding Venues!

Aug 17 – 24

$112 per night
Superhost

Cottage in Branford

4.86 out of 5 average rating, 195 reviews

Cozy Home In Short Beach Community

Nov 4 – 11

$166 per night
Guest favorite

Apartment in East Haddam

4.89 out of 5 average rating, 102 reviews

Penny Corner Airbnb

Jan 8 – 15

$90 per night
Guest favorite

Cottage in Guilford

5.0 out of 5 average rating, 80 reviews

Waterfront Joshua Cove Cottage with private beach.

Dec 8 – 15

$364 per night
Superhost

Guesthouse in Branford

4.79 out of 5 average rating, 47 reviews

Studio on the shore - Short Beach - Water Views

Sep 24 – Oct 1

$99 per night
Guest favorite

Cottage in Guilford

5.0 out of 5 average rating, 15 reviews

Waterfront Cottage With Unforgettable Views

Feb 4 – 11

$395 per night
Superhost

Cottage in Guilford

4.88 out of 5 average rating, 8 reviews

Your own Thimble Islands private cottage!

Aug 13 – 20

$895 per night
Guest favorite

Vacation home in Guilford

4.98 out of 5 average rating, 59 reviews

Spacious Oceanfront Getaway with Spectacular Views

Feb 3 – 10

$500 per night

Destinations to explore