Beachfront vacation rentals in Oak Beach-Captree

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Top-rated beachfront rentals in Oak Beach-Captree

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Guest favorite

Home in Shirley

4.98 out of 5 average rating, 208 reviews

Luxurious Waterfront Beach House On The Bay

Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

Superhost

Home in Fair Harbor, Fire Island

4.9 out of 5 average rating, 30 reviews

Chill Beachfront Cottage Amazing Bay/Sunset Views!

Charming, Classic Beach Cottage right on the BEACH! with Panoramic Views & Sunsets on the Great South Bay! Summer on Fire Island is truly paradise. The ocean is sensational, the weather is perfect, the sunrises & sunsets are spectacular, the residents are friendly & creative, & life is WONDERFUL. Our Cottage has 5 Bedrooms with 8 beds that sleep 11. Like Fair Harbor, it has a casual, laid back vibe that is comfortable & enjoyable for people of all ages. * KAYAKS are AVAILABLE! Ask Roberto

Top guest favorite

Home in North Fork

5 out of 5 average rating, 20 reviews

Hang by the (Chel)SEA

Enjoy a relaxing stay with family and friends at this cozy soundview beach house. Wake up to breathtaking views of the water, where you can go right into the back yard of your very own private beach! Have a morning coffee on the front balcony of the home that overlooks the beautiful marshlands and then spend the day relaxing on the beach, or kayaking in the water! End the evening with a glass of wine on the back deck, that overlooks the water with the most spectacular sunsets!

Superhost

Home in Suffolk County

4.83 out of 5 average rating, 42 reviews

Bay Front Upper Level Cottage 47E

Beach front on the water. This paradise hosts its own private beach located on the bay. The house is close to the ferry and easily accessible to restaurants and everything Fire Island has to offer. The house boasts an outdoor shower, 2 bedrooms, kitchen, an indoor full bathroom, half bath, and a grill. Located on the 2nd floor and has views of the bay, beach, and sunset from every direction. Perfect for a family get away or a couple looking to have a romantic trip.

Guest favorite

Home in Cherry Grove, Fire Island

4.97 out of 5 average rating, 93 reviews

Bayfront Fun - 3 BR & 3 Ensuite Bath with Hot Tub!

Location Location Location! This newly appointed modernist home resides directly on the Bay and is three blocks east of town...only five minutes from shopping and nightlife. The house is also on a direct 2 minute walk to the Ocean and its Bay views are spectacular! The unit features nine foot sliding glass doors that open sixteen feet wide leading you from the living space to the sprawling Bayfront cedar deck, it's an amazing indoor/outdoor experience.

Top guest favorite

Home in Miller Place

4.87 out of 5 average rating, 85 reviews

Glen Laurel on the Sound (w/private beach)

Glen Laurel on the Sound is located on the North Shore of Long Island. It's a colonial style home that sits in the middle of an expansive property, offering privacy and the ability to spread out and enjoy the endless possibility of sprawling lawns bounded in only by trees. Sitting atop a bluff that provides unimpeded views of the Sound and the Connecticut shoreline, is the home with a columned front porch that cannot be beat, particularly at sunset.

Guest favorite

Home in Shirley

4.95 out of 5 average rating, 41 reviews

Waterfront Designer Stay • Sunsets • Near Beach!

Welcome to The Swan House 🦢🏡 —your peaceful, designer retreat on Bellport Bay. Enjoy stunning sunsets, swans gliding by, and direct water access from the backyard. Relax on the spacious deck, fire up the grill, or take a short drive to Smith Point Beach. Inside, you’ll find an open, sun-filled layout with curated furnishings and a calming coastal vibe. This stylish escape offers serene waterfront living in any season—just 90 minutes from NYC.

Guest favorite

Home in Shirley

4.96 out of 5 average rating, 137 reviews

Beach Waterview, 3 KING Beds, Golf Putting Green

Take it easy at this 3 story waterview beach home with a putting green and fire pit. The Bellport Bay is across the street. Shirley Beach: 0.4 mile walk Smith Point Beach: 1.8 miles Featuring: 3 luxurious KING beds 👑 (and 2 fulls) Watch Netflix, Disney+ on the 70" living room TV and 3 50" bedroom TVs Fully equiped kitchen/dining room Enjoy BBQ Grill, fire pit on premium soft turf Highspeed mesh WiFi, keyless entry.

Superhost

Home in Bay Shore

4.78 out of 5 average rating, 49 reviews

The Bay Side House- Entire Home

Relax with the whole family or friends at this peaceful place to stay that’s close to it all!! 4 surrounding restaurants in walking distance. ( captain bills, Nicky’s on the bay, fat fish and swept away) Down town Bay Shore with tons of shopping, restaurants and night life. Fire Island- just a 1/2 hour boat ride away with ferries in walking distance or a short Uber ride. Robert Moses State Beach- 15 minute drive.

Guest favorite

Home in Arverne

4.95 out of 5 average rating, 84 reviews

Beach Front Escape - Rockaway Beach NYC

First floor apartment of a beachfront townhouse on NYC's premiere surf beach! Located right on the boardwalk and beach, and 5 min walk from the subway. 45mins to Manhattan and only 2 stops from JFK. Guest suite and shared back yard. 1300 sq ft 2 bedroom, 2 bath. Smart lock entrance + parking pass for private roads available. Come breathe the fresh salt air and avoid the normal NYC crowds. This is a hosted stay.

Guest favorite

Townhouse in Arverne

4.94 out of 5 average rating, 140 reviews

Incredible Beach House -Spectacular Ocean View!

We do have short-term rent permit from the OSE. Perfect house if you are looking to get away from the city for a few weeks, you are visiting NYC but don't want to stay in the urban chaos, or just want to treat yourself with a perfect vacation. This newly-renovated beach house IS THE NUMBER ONE LOCATION and most luxurious house in the community. RIGHT BEFORE THE WATER WITH THE MILLION DOLLAR VIEW!

Guest favorite

Apartment in Fire Island

5 out of 5 average rating, 11 reviews

Studio with Deck steps to the beach

Studio Apartment with private deck only a few steps from the beach at Dune Point Guesthouse. Located in Cherry Grove, Fire Island. Only accessible by Ferry! Adults Only Resort! Fully equipped kitchen, outdoor loveseat, table and chairs on you private deck... perfect for a few days stay, BBQ, cook, enjoy the beach