1-2 Bedroom Rentals

$2950
per week

Attwood Barn ❄️

Simple 2 bedroom cottage on the northern end of Corn Neck Road, just south of Sachem Pond.
Across the street from the Sacred Labyrinth and a short walk from entrances to Nature Conservancy Trails. A/C!

$2000
per week

Beach Ave. Cottage

Very basic artist's cottage with beautiful views of Trim's Pond & the ocean.

$2950
per week

Butler Cottage

RE.01951-STR, STR-25197

Vintage island cottage with fantastic ocean views over the eastern Atlantic and north to Clay Hear. Walking distance to town and approximately 1 mile to Southeast Lighthouse.

$3100
per week

Dupont Cottage

RE.00182-STR, STR-25086

One of three houses on 17+ acres off Beacon Hill Road. Overlooking lush countryside.

$3200
per week

Ferraro Condo, #1 🐾❄️🏊

RE.01810-STR, STR-25260

Convenient ground-floor dog-friendly condo at Salt Pond Settlement in New Harbor with Great Salt Pond views and a community pool.

$2000
per week

Flounder In

RE.02574-STR, STR-25143

Charming and simple cottage with ocean views and a spacious yard.

$3200
per week

Harbor Pond Cottage

RE.02563-STR, STR-25357

Perfect location to walk to Old Harbor and New Harbor areas with ease. The property is shared by the Harbor Pond Cape. Enjoy water views from every room and direct access to the back of the Great Salt Pond.

$2600
per week

Kentuck Meadow

RE.00547-STR, STR-25261

Adorable two bedroom burger cottage with fantastic views and a large yard on Coast Guard Road. Walk to 3 beaches and New Harbor.

$2720
per week

Knapp

RE.06640-STR, STR-25372

This is a whimsical, simple artist cottage with an enclosed porch and phenomenal ocean views on the quiet West Side.

$2600
per week

Knous

RE.02527-STR, STR-25135

Quaint home located in a residential neighborhood just a short bike ride to town.

$3150
per week

Luna

RE.02217-STR, STR-25138

Rustic home with open floor plan and nice second story deck.

$2410
per week

Ocean Echoes Apartment

RE.00599-STR, STR-25064

Lovely second floor apartment close to Old Harbor, New Harbor and beautiful sandy beaches.

$4230
per week

Swain Cottage

RE.06318-STR, STR-25110

Simple, fisherman's cottage with water views from every window. Beautiful ocean views to the west and expansive Cormorant Cove and Great Salt Pond views to the east. Private access to Charleston Beach and a quick walk from the Coast Guard Station and Coast Guard Beach, a family favorite for watching all the boats come and go from the pond.

3 Bedroom Rentals

$4500
per week

Bayberry Cottage

RE.01388-STR, STR-25167

Private, Corn Neck home surrounded by stone walls and Greenway Trails with peeks of the North Lighthouse. A large yard with wrap around decking is perfect for entertaining!

$4700
per week

Beacon Hill House

RE.02544-STR, SRT 25081

Beautifully maintained home with great kitchen & yard for entertaining. Comfortable house in a quiet area yet just over a mile from the beach & town!

$12,750
per week

Bluff Beachouse

RE.03516-STR, STR-25466

Beautifully updated home, dramatically perched atop the Mohegan Bluffs with sprawling ocean views. Features an impressive staircase down to the beach below, a favorite for fisherman and surfers alike. Coastal living at its best!

$3500
per week

Calypso

RE.02481-STR, STR-25204,

Light and airy summer home overlooking Fresh Pond with a spacious yard and deck for outdoor enjoyment.

$4800
per week

Cindy’s Meadows 🐾

STR-25446

Great location right at the end of Mansion Road, walking distance to Mansion Beach!

$4100
per week

Desantis 🐾

RE.06475-STR, STR-25320

Delightful island cottage in a remote area down a dirt road with a big yard and beautiful ocean and sunset views.

$3950
per week

Dunn Cottage 🐾

RE.00182-STR, STR-25086

Large home on the west side with ocean and sunset views. 5 minute walk to Gracie's Cove Beach.

$5150
per week

Francis Sprague

RE.06639-STR, STR-25351

Privately located on a long dirt road between Gracie's and Dorrie's Coves. New kitchen, nice outdoor deck space with a large open yard, sunset and ocean views.

$4,650
per week

Havenhood 🐾

RE.04758-STR, STR-25073

This charming, pet-friendly home is nestled on the quiet west side of the island, offering a spacious yard and pretty sunsets. Just a 15 minute walk to Cooneymus Beach or Rodman's Hollow.

$3800
per week

Hill House ❄️

RE.03864-STR, STR-25094

Sweet and simple 3 bedroom cottage nestled atop a hill with ocean views in the distance.

$3100
per week

Hilltop Cottage 🐾

RE.01549-STR, STR-25190

Rustic and simple cottage on the southwest side with old-Block Island charm. Pretty ocean views, walking distance to Cooneymus Beach.

$9250
per week

Horsieville ❄️🏊

RE.02567-STR, STR-25405

Private home off of Lewis Farm with inground pool, just a short walk to Rodman’s Hollow and close to the best West side beaches. Watch the sunset from the porch of the stone patio or while floating in the pool. Relax in the jetted tub in the master bathroom after a long hike through Rodman’s Hollow.

$3200
per week

Ives – Cole Cottage

RE.00681-STR, STR-25125

A waterfront cottage on the Mohegan Bluffs with great views with an updated kitchen.

$4250
per week

La Dolce Vita 🐾

RE.01267-STR, STR-25346

Pretty ocean and Southeast Lighthouse views from this open and airy home. Located on Mohegan Trail just under half a mile from the Mohegan Bluff stairs and half a mile to Southeast Lighthouse.

$4500
per week

Lewis Farmhouse

RE.06472-STR, STR-25121

Walking distance to Nature Conservancy trails, this lovely restored farmhouse was just completely redone in '22-'23 & features beautiful water views off the SW side of the island.

$5050
per week

M.O.D.Y.C.

RE.06629-STR, STR-25252

Charming, classic Block Island home with spectacular views of the ocean and Cormorant Cove. Direct beach access down a private path.

$3850
per week

McPhee 🐾

RE.02552-STR, STR-25425

Comfortable, and quiet, desirable Southwest Point location with a fabulous yard surrounded by mature trees and stone walls. Fantastic sunsets!

$4200
per week

Meadows

RE.06356-STR, STR-25089

Private, serene cape surrounded by stone walls and conservancy land, with peeks of ocean.

$4700
per week

Ocean Sunset Cottage

RE.00205-STR, STR-25325

Charming cottage with great ocean and sunset views, just a short walk to Cooneymus Beach.

$4500
per week

Olives

RE.06541-STR, STR-25169

Home with large deck and yard with fantastic ocean and sunset views located just off Corn Neck Road, approximately 1 mile to Mansion Beach and North Light.

$5980
per week

Osprey Nest

RE.06270-STR, STR-25378

Unparalleled location right on Sachem Pond with a shared private path right to the waters edge. Bring your kayak and enjoy the serenity of the area.

$4300
per week

Peg’s House ❄️

RE.02453-STR, STR-25377

Enjoy a private property on Cooneymus Road with a sunny wrap around porch and central AC. Just a short walk to Cooneymus Beach or Rodman's Hollow!

$3780
per week

Pheasant’s Crossing

STR-25366

Sweet, updated West Side cottage with distant ocean views and sprawling yard.

$5150
per week

Purple Wave ❄️

RE.00663-STR, STR-25338

Quiet and private neighborhood. Walking distance to the ferry and downtown. Spacious yard and home with AC.

$4030
per week

Raphael 🐾

STR-25350

Former artist's home, this west side location has privacy, ocean and sunset views. Walking distance to Cooneymus Beach.

$5000
per week

Rule

RE.06351-STR, STR-25447

Spacious home located on the quiet and peaceful West Side off of Cooneymus road with fantastic, long-range ocean views. Includes private decks off 2 bedrooms and a large yard.

$3980
per week

Schlesinger

RE.04759-STR, STR-25254

Walk to Mansion Beach on private right-of-way from this spacious, relaxed yet stylish house. A bright spacious home with beautiful gardens and art by local artists. Inspired by the beauty and tradition of New England farm barns.

$5250
per week

Sunset View (previously Hollrock)

RE.25124-STR, STR-25124

Beautiful three story home with an inverted floor plan and multiple decks. Enjoy sweeping westerly views from Montauk Point, NY to the RI & CT coastline. Spectacular sunset views! Located on the desirable Corn Neck Road side of the island just a short walk from the beaches.

$3500
per week

West Side Cape 🐾

RE.06022-STR, STR-25337

Quiet retreat on the west side with large yard and deck with spacious bedrooms and comfortable living spaces.

4 Bedroom Rentals

$6300
per week

A&A Tea Room 🐾❄️

RE.02478-STR, STR-25091

Updated iconic West Side home with lovely private yard and pretty, distant ocean views.

$4710
per week

Battyville

RE.02566-STR, STR-25356

Located off of Corn Neck Road in a small neighborhood that shares a private path to Mansion Beach. Leave the car at the rental and walk to and from the beach all day in 8-10 minutes. A balcony off the master bedroom provides beautiful, island, pond, and distant ocean views.

$4600
per week

Cheers *newly renovated

RE.06810-STR, STR-25403

Located in the much coveted Sheep's Meadow off Corn Neck Road with shared private access to Mansion Beach walking distance from house. This cottage is currently undergoing renovations, photos will be updated as they become available.

$5400
per week

Cypress Glen 🐾

RE.00176-STR, STR-25308

Peaceful & relaxing setting, over 2 acres, tucked away from the hustle & bustle of town yet less than a mile from the center of town!
Added bonus of 2 separate dwellings: a 3 bedroom house and a 1 bedroom cottage!

$4100
per week

duPont Farmhouse 🐾

RE.02526-STR, STR-25345

Lovely antique farmhouse filled with old Block Island charm. Private location with rolling hills, winding trails and distant ocean views. Dog-friendly!

$5150
per week

Harbor Pond Cape

RE.02563-STR, STR-25357

This perfect location offers an easy walk to both Old Harbor and New Harbor. The property is shared by the Harbor Pond Cottage. With direct access to the back of the Great Salt Pond, bring your kayaks, or just enjoy the water views from the deck.

$6250
per week

Isaac’s Corner 🐾❄️

RE.06345-STR, STR-25107

Enjoy distant ocean views and close proximity to Fresh Pond from this spacious 4 bedroom home with comfortable living areas and a large yard. A/C in living room and primary bedroom.

$3650
per week

Kurz Cottage

RE.01964-STR, STR-25157

Walk to mansion beach from this simple 4 bedroom house in private setting with spacious yard.

$4600
per week

Mid-Century Modern House

RE.05036-STR, STR-25326

Unique home on the West Side, owner/architect indoor/outdoor design. Pretty meadow, pond &180 degree ocean views.

$5380
per week

Moby Rock 🐾

RE.01687-STR, STR-25096

Spacious deck and large yard with ocean views over the iconic Spring House. Conveniently located right off Pilot Hill, near the BI School, under 1 mile from the ferry and downtown.

$10100
per week

Morning Glory ❄️

RE.01143-STR, STR-25333

Dramatic location overlooking Mohegan Bluffs, 5 minute walk to the beach. Impressive and pristine home.

$5650
per week

Szabo

RE.00179-STR, STR-25170

Spacious home in a pretty country setting with pond views. Very private but close to town and beaches.

$4150
per week

Tangney Cottage

RE.01240-STR, STR-25328

Lovely recently renovated cottage, walking distance to Old Harbor with pretty water views over town

$5150
per week

The View 🐾

RE.01872-STR, STR-25244

Amazing ocean and island views from this hidden gem off Gracie's Cove Road on the west side.

$5300
per week

Weisbroat 🐾

RE.03569-STR, STR-25382

Spacious 3 bedroom house with a bonus bedroom, full bathroom and living room area above the garage on the west side.

5+ Bedroom Rentals

$12400
per week

Bamboo Grove 🐾

RE.06245-STR, STR-25268

What was once a BnB, this large, refurbished home combines old world appeal with modern comfort, nestled amidst lush greenery and surrounded by stone walls. With two distinct wings to the building, this property is ideal for two families or large groups looking to unwind and enjoy each other's company. The brand new kitchen is sure to impress guests and become the heart of the home during their stay!

$5550
per week

Dupont Middle House

RE.02517-STR, STR-25222

One of three houses on 17+ acres off Beacon Hill Road. Enjoy lovely pastoral views from the convenient screened-in porch of this charming house.

$6150
per week

Dupont Parsonage

RE.02483-STR, STR-25099

One of three houses on 17+ acres off Beacon Hill Road. Spacious yard, small screened-in porch and old island charm.

$6250
per week

Georgian Farmhouse 🐾

Lovely 4 bedroom house with 1 bedroom cottage conviently located right off Corn Neck Road across from Andy's Way. Shares a private walking path to Mansion Beach with neighboring homes.

$6550
per week

Hardy Smith House

RE.01227-STR, STR-25383

Large, former BnB located steps from town with private yard and pretty views of Old Harbor.

$6250
per week

Marchesi 🐾

RE.00193-STR, STR-25343

Sun drenched, tastefully decorated Post and Beam home with 3 levels of living space, close to town and the Southeast Lighthouse, with beautiful distant ocean views and a private, lush yard. 

$8320
per week

Sunset Hill 🐾❄️

RE.02900-STR, STR-25334

Large home just a short walk from town with plentiful sleeping space! Walking distance to town!

$9500
per week

The Holiday Haven

RE.06573-STR, STR-25259

This historic B&B converted into a single-family rental offers an exciting vacation opportunity for a large family. Fabulous views a short bike ride away from beaches and restaurants!

$6200
per week

The Islander

RE.06658-STR, STR-25385

Historic B&B, the Islander embodies vintage island charm & convenience of walking distance to town, the ferry & the beach.

$9400
per week

Turning Point

RE.06271-STR, STR-25379

Beautiful family compound with uninterrupted views of the ocean, wildlife, and the North Lighthouse.

$8750
per week

Tweedy

RE.01176-STR, STR-25362

Located directly on Great Salt Pond with stairs to beach on Cormorant Cove. Beautiful views of the cove, Great Salt Pond and the ocean.

$5570
per week

Vail

RE.01679-STR, STR-25267

Wonderful summer rental with fantastic ocean views and shared stairway to the Vail Beach.