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Holiday houses in Smith Island

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Quick stats about holiday rentals in Smith Island

  • Total holiday rentals

    Explore 10 holiday rentals in Smith Island

  • Nightly prices starting at

    Smith Island holiday rentals start at $176 NZD per night before taxes and fees

  • Verified guest reviews

    Over 840 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Wi-Fi availability

    10 of Smith Island holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Smith Island rentals

  • 4.8 Average rating

    Smith Island stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated holiday rentals in Smith Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Smith Island

Visit the HH Ranch for our favorite season Autumn!

Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. Comfortable family room with seating for 5. Updated enclosed patio is ideal in the summer. Large kitchen fully stocked to cook your meals. New front deck. Large bathroom with dual rainhead shower. Easy access to the water. Bikes and SUP available in the shed. Kayaks are covered outside by shed. Island is only accessible by boat. Enjoy the tranquility of this unique place.

LocationBikingCleanliness

4.96 out of 5 average rating, 26 reviews
Top Guest favourite
Cottage in Smith Island

IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental

Unwind and relax after the busy life in the city. Get comfortable and enjoy plenty of extra space in this inviting retreat. Wake up refreshed and ready for a day of kayaking, bicycling and or exploring the island. Just four houses down, you'll find our deep-water dock--perfect for crabbing, launching kayaks, mooring your boat, or simply soaking in the peaceful surroundings. After a day of adventure, rinse off in our spacious hot and cold shower for a refreshing, nature inspired experience.

LocationFamilyAccess

5.0 out of 5 average rating, 70 reviews
Top Guest favourite
The image features a new white single-story home with a front porch, surrounded by greenery. Below, a sandy beach area is visible with a blue and white striped umbrella, leading to calm waters. A wooden pier extends into the bay.
Home in Reedville

Summer Breeze waterfront new home-Private Beach

FALL & WINTER RATES AT UP TO 50% OFF FOR 2026! Summer Breeze, located on the Chesapeake Bay in the fishing village of Reedville, is our new 3 Bedroom, 2 Bath home with waterfront shoreline and beach on a peaceful cove. The neighborhood beach, which is for residents and guests renting, fronts directly on the Chesapeake Bay and is just a few lots, and a short walk away. The gentle Bay beach with soft sand, gentle waves, and gently sloping bottom are perfect for fun and play for the whole family!

LocationFamilyCheck-in

4.94 out of 5 average rating, 89 reviews
Top Guest favourite
A wooden deck is shown overlooking a serene pond, framed by lush trees. A dining table with chairs is set for outdoor enjoyment, while soft natural light reflects off the water's surface, creating a peaceful ambiance.
Farm stay in Onancock

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

FamilyLocationPets

4.99 out of 5 average rating, 352 reviews
Top Guest favourite
A three-story home is showcased at sunset, reflecting beautifully in the calm water. Wraparound porches provide shaded areas, and nearby greenery enhances the natural setting. The tranquil surroundings suggest a serene atmosphere for relaxation.
Home in Smith Island

Island Time (whole house rental)

3 story home with 2 wrap around porches. One first floor room and three second floor rooms-including a master suite. The third floor is a loft with sleeping for 5 and a full bath. Breathtaking views of sunrises and sunsets. Life on the island is laid back. Visit us to get away from the fast pace life. We offer complimentary bikes, kayaks, fishing poles, crab nets, porch swings, hammock, hot tub, etc. Golf Carts available for rent. Breakfast and STEAMED CRABS are available for a charge.

ValueFamilyNearby

4.96 out of 5 average rating, 71 reviews
Top Guest favourite
Home in Heathsville

Luxury Beach Hs w/ 4 Suites, PrivateBeach & Htub

Escape to Cottage Serenity Shores, a peaceful, private beachfront retreat where the Potomac River meets the Chesapeake Bay, offering calm views and gentle shores. This modern coastal home is surrounded by pines and dunes for seclusion. Unwind on the massive deck with panoramic views, fire pit, and hot tub. Watch the sunrise on the private pier overlooking the beach. Enjoy your large private beach steps away. Sleeps 12-14. Pure tranquility—no crowds, just nature's calm.

FamilyLocationAmenities

5.0 out of 5 average rating, 18 reviews
Guest favourite
The exterior of a two-story house is shown, featuring a light-colored façade and multiple windows. A staircase leads to an entrance at the front. A well-maintained lawn surrounds the structure, and a friendly corgi is visible on the grass.
Guest suite in Crisfield

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

ValueLocationView

4.78 out of 5 average rating, 283 reviews
Top Guest favourite
An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.
Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

September 12-16 available. Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.

FamilyLocationPets

4.99 out of 5 average rating, 266 reviews
Top Guest favourite
The exterior of the cottage is shown, featuring a welcoming entryway with stairs and a blue door. Two blue adirondack chairs are positioned on the well-maintained lawn, with a glimpse of the waterfront visible through large windows. Surrounding greenery enhances the outdoor setting.
Cottage in Smith Island

Levering Creek Cottage with private dock

Levering Creek Cottage is a waterfront property with a deep water dock that you can see from the back door. We are located on Levering Creek where you can sit on the dock watching watermen arrive with their daily catch, see nesting bald eagles, watch beautiful sunrise, fish and crab. We are also just steps away from most everything including the ferry.

LocationValueIndoor spaces

4.97 out of 5 average rating, 274 reviews
Top Guest favourite
A one-story white house is surrounded by a green lawn and is enclosed by a fence. The home features a peaked roof and small front porch, with large windows allowing natural light. A decorative sign is positioned in front, marking the property.
Home in Tangier

Island Oasis, Tangier Island, Virginia

Island Oasis is a one story, waterfront, newly renovated home situated in the heart of town. The tour boat docks are directly behind property with a gift shop on site. Restaurant, ice cream/sandwich deck, grocery store, church, museum , etc are all within walking distance. Guests will have full access to home and a nice deck overlooking harbor.

LocationFamilyView

5.0 out of 5 average rating, 172 reviews
Top Guest favourite
A wooden boardwalk leads to a charming beach cottage, flanked by sandy beach and lush greenery. The cottage features large front steps, a light-colored exterior, and multiple windows offering views of the surroundings. The peaceful shoreline setting enhances the inviting entrance.
Cottage in Deal Island

Private Beachfront Cottage with 2 Bedrooms + Loft

Relax and enjoy your own private beach with panoramic views of the Chesapeake Bay! Our cottage is in a quiet strip of Deal Island shoreline, but still boasts high speed internet - so you don't have to completely disconnect while you're here ...unless you want to, of course. We won't tell.

LocationFamilyBarbecue

4.94 out of 5 average rating, 100 reviews
Guest favourite
Home in TYLERTON

3 bedroom/2.5 bath Smith Island bungalow with dock

The Quietness of the island and the beautiful scenery around the waters edge. You will hear the birds and the waves and the wind. The island is void of loud noises, mostly nature. The home was built around 1860 and fully restored 2008. its perfectly imperfect!

FamilyLocationAir conditioning

4.95 out of 5 average rating, 153 reviews

Popular amenities for Smith Island holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Smith Island

Top Guest favourite
A charming two-story cottage features a traditional white exterior with black shutters framing multiple windows. A welcoming front porch is accessed by a brick pathway, while a mailbox stands at the edge of the neatly maintained lawn. Stately trees provide a backdrop.
Home in Crisfield

Cozy Crisfield Cottage

FamilyLocationNearby

4.93 out of 5 average rating, 69 reviews
Top Guest favourite
A serene swimming pool is illuminated in soft purple hues against a twilight backdrop. Two individuals can be seen enjoying the water. Tall trees surround the area, and a glimpse of the waterway is visible beyond the pool, enhancing the tranquil atmosphere.
Home in Heathsville

Waterfront home-225' pier kayak firepit pool beach

FamilyLocationBathroom

5.0 out of 5 average rating, 27 reviews
Guest favourite
A light-colored couch with striped black and white pillows is positioned in a spacious living area. A round, dark wood coffee table sits in front of the couch, accompanied by a soft area rug. Natural light enters through two nearby windows, illuminating the room.
Home in Crisfield

Catch of the Bay

ValueLocationParks

4.95 out of 5 average rating, 81 reviews
Top Guest favourite
The exterior of a three-story house is displayed, featuring a white facade with blue accents on the roof. A bay window is visible on the second level, framed by lush greenery, while a small flower bed is positioned in front. The property is surrounded by a well-maintained lawn.
Home in Deal Island

The Tangier Escape

LocationFamilyIndoor spaces

4.97 out of 5 average rating, 31 reviews
Top Guest favourite
Home in Reedville

The Haven On The Chesapeake Bay

FamilyLocationWi-Fi

5.0 out of 5 average rating, 94 reviews
Guest favourite
The two-story farmhouse is surrounded by a spacious yard, highlighted by a prominent American flag flying in front. Large windows allow natural light, while the earthy green exterior blends with the surrounding trees. A charming white bench adds to the inviting outdoor space.
Home in Deal Island

Rusty Anchor

FamilyValueBackyard

4.94 out of 5 average rating, 51 reviews
Guest favourite
A cozy living area features a brown leather sofa and an armchair, both adorned with decorative pillows. A woven coffee table sits in the center, while a side table with a lamp provides soft lighting. Natural light filters in through large windows, enhancing the warm ambiance.
Cottage in Reedville

Bayberry - awesome Solo Stove Fire Pit

LocationValueHospitality

4.88 out of 5 average rating, 89 reviews
Guest favourite
An aerial view depicts a private above-ground pool surrounded by a spacious wooden deck. Multiple seating areas with umbrellas offer shade, and lush greenery borders the property, adding a natural ambiance. The outdoor kitchen and grill area are visible, enhancing the deck's recreational space.
Cottage in Marion Station

Pool/HotTub/RecRoom/Pvt. Dock YearRoundPlayground

FamilyLocationHot tub

4.81 out of 5 average rating, 59 reviews

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Smith Island?

    Smith Island has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Smith Island?

    Experience the best of Smith Island with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Smith Island have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Smith Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Smith Island have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Smith Island. Enjoy a tailored experience with all the comforts you desire.