1-2 Bedroom Rentals

$3050
per week

Butler Cottage

RE.01951-STR, STR-25197

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

$3300
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, A/C and a community pool.

$3500
per week

Harbor Master Cottage 🐾❄️

RE.020096STR, STR-26064

This 2 bedroom (1 king, 1 queen, 1 single) home is conveniently located off Old Town Road, walking distance from town and beaches.

$3370
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.

$2750
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.

$2770
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.

$3260
per week

Luna

RE.02217-STR, STR-25138

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

$2510
per week

Ocean Echoes Apartment ❄️

RE.00599-STR, STR-25064

Lovely second floor apartment with A/C close to Old Harbor, New Harbor and beautiful sandy beaches.

$3300
per week

Ripple

STR-26061

Updated condo on the top floor of the historic Masonic Hall Building. Five minute walk to / from the ferry terminal, shops, and the beach.

$3550
per week

Saltside, Unit 6 🐾❄️🏊

RE.08114STR, STR-25538

This renovated condo at the popular Salt Pond Settlement offers comfort, A/C, and beautiful views of the Great Salt Pond.

$4430
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.

$3295
per week

Wilson Spring Lot 🐾

RE.06908-STR, STR-25387

This rental off of Cooneymus Beach Road offers a cozy retreat with 2 bedrooms, 1 bathroom, and an outdoor shower for a refreshing experience.

3 Bedroom Rentals

$4300
per week

Allen’s Cottage 🐾

RE.06474-STR, STR-25329

Enjoy beautiful views and a short walk to a west side beach, perfect for watching sunsets!

$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.

$4700
per week

Beacon Hill House

RE.02544-STR, SRT 25081

Nicely maintained home featuring a stylish kitchen and spacious yard—perfect for entertaining.

$12,950
per week

Bluff Beachouse

RE.03516-STR, STR-25466

Beautifully updated home, dramatically perched atop the Mohegan Bluffs with sprawling ocean views.

$3450
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!

$4050
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.

$5250
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.

$4,850
per week

Havenhood 🐾

RE.08171-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.

$4150
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.

$3300
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.

$3570
per week

Ives – Cole Cottage

RE.00681-STR, STR-25125

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

$4910
per week

La Dolce Vita 🐾

RE.01267-STR, STR-25346

Stunning ocean and Southeast Lighthouse views from this inverted, open and airy home.

$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.

$5175
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.

$4050
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!

$4600
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.

$4600
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.

$6730
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.

$5180
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.

$3650
per week

Radigan Star

STR-25359,

Private coastal farmhouse with water views, wood interiors, wraparound deck, and unforgettable sunsets over Grace’s Cove.

$4230
per week

Raphael 🐾

STR-25350

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

$3,650
per week

Rolling Knolls

RE. 0200155-STR,

Cozy 3-bedroom, 1.5-bath home with a first-floor bedroom, large private yard, and inviting deck.

$5270
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.

$5750
per week

Sunset View

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!

$3650
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

$6800
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.

$4910
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.

$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.

$4300
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.

$6150
per week

Edward Ball House ❄️🐾

This is the oldest house on the island, set in a private pastoral setting while still being centrally located for easy access to town and beaches.

$5350
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.

$6700
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.

$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.

$4700
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.

$5680
per week

Moby Rock 🐾

RE.01687-STR, STR-25096

Spacious deck and large yard with ocean views overlooking the iconic Spring House.

$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.

$4800
per week

Russinoff

Spacious four-bedroom home located directly across from Mansion Beach Road.

$5900
per week

Seawatch

STR.25371

This newly updated rental home sits just off Grace’s Cove, offering a quiet retreat with beautiful ocean views.

$5900
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.

$5250
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.

$5,500
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

$12,400
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.

$5800
per week

Cypress Glen 🐾

RE.00176-STR, STR-25308

Peaceful 2-acre retreat just a mile from town, featuring a 3-bedroom house and a cozy 1-bedroom cottage.

$6000
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.

$6500
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.

$6550
per week

Georgian Farmhouse 🐾

Lovely 4 bedroom house with 1 bedroom cottage conviently located right off Corn Neck Road across from Andy's Way. Beautiful views of the Great Salt Pond and the ocean.

$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.

$6405
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. 

$8920
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.

$10,400
per week

Turning Point

RE.06271-STR, STR-25379

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

$8950
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.

$5770
per week

Vail

RE.01679-STR, STR-25267

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