Vacation rentals in Loblolly Bay

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Top-rated vacation rentals in Loblolly Bay

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Guest favorite

An expansive villa is shown from an elevated viewpoint, surrounded by vibrant tropical vegetation and flowers. A shimmering pool is visible in the foreground, cascading into the deep blue Caribbean Sea, with distant islands outlined against a clear sky.

Home in Virgin Gorda

5 out of 5 average rating, 13 reviews

Island Spice, 2 BRs, Free Tennis, Squash, Gym

Dramatically sited above the Caribbean Sea, Island Spice villa treats guests to a memorable island holiday. Two matching bedroom/bathroom suites, furnished in island décor, flank the greatroom and are separately accessed from the deck. All rooms offer full sea and garden views through large sliding windows and doors. Spend casual hours on the villa’s long, spacious shaded deck with spectacular 180 degree panoramic vistas of the Sir Francis Drake Channel and the British Virgin chain of islands.

Guest favorite

Villa in Marina Cay

5 out of 5 average rating, 6 reviews

Aloe House at Diamond Reef

Luxury 3BR old world waterfront estate w/ amazing views on a private island within a 100 steps to the sea. Sitting on the covered veranda, guests have views of 7 sisters islands, but not a house in site. Walk to the beach or snorkel Diamond Reef. The ultimate in privacy yet just 5 min to restaurants and beach bars for live music. Paddle boards & snorkel gear. There is a small SUV to get from beach to house, and a 18' boat that is used to take you to Scrub Island, Trellis Bay, or Marina Cay.

Superhost

Aerial view of the villa showcasing the circular covered deck and its inviting private plunge pool. Adjacent lounge chairs and a small table are visible on the wooden patio. Lush greenery surrounds the space, blending architecture with the natural environment.

Villa in Virgin Gorda

4.93 out of 5 average rating, 75 reviews

Sundowner romantic 1BR beachfrontvilla privatepool

Sundowner reigns as Virgin Gorda's most sought-after honeymoon villa. This majestic yet romantic beachfront villa, with a street address of 1 Paradise Lane within Nail Bay Estate, impresses guests with its royally inviting decor. Sliding glass doors on this villa's private patio lead to the inside dining and living areas, and the open-plan spacious gourmet kitchen. The view from the throne bed overlooks the turquoise sea and the cloud-strewn azure sky with colors custom-made in the Caribbean.

Guest favorite

A panoramic view captures the vibrant blues of the Caribbean Sea meeting the shoreline. Lush greenery frames the image, with rocks visible near the water's edge. In the background, distant islands emerge against a clear sky, scattered clouds providing texture.

Home in VG

4.86 out of 5 average rating, 81 reviews

Sunset Watch-Affordable luxury on a beachfront lot

A whimsical tropical mural hand painted by a local artist on the front wall welcomes you to Sunset Watch at Nail Bay. Incredible sunsets. Central air-conditioning. High speed fibre optic internet with 150 +/- tv channels. New modern gourmet kitchen. Large sundeck near a sparkling turquoise pool. Snorkeling equipment available. Complimentary access to Nail Bay Sports Club with a/c gym.Please note that Sunset Watch and 1 Paradise Lane share a pool when both villas are occupied. .

A bright living space features a blue sofa and wooden coffee table, surrounded by light-colored flooring. A dining table with a blue runner is set for four, while the kitchen area is visible in the background, showcasing modern appliances and cabinetry. Natural light filters through open doors.

Cottage in Loblolly Bay

4.76 out of 5 average rating, 21 reviews

2 bedroom cottage on the beach! Full kitchen & AC

“Purple Cottage” Caribbean cottage charm that is unique to Anegada, but now with beautiful modern amenities and a property with lots to do! Location is everything here. Step out of your cottage and into the sand at beautiful Loblolly Bay. We located on one of the most beautiful beaches and coral reefs in the Caribbean (and on most days you will have it all to yourself). Snorkeling, relaxing, walking to get a drink, stargazing, or taking an adventure tour. A private slice of heaven!

Guest favorite

An aerial view captures the serene landscape of Anegada, showcasing sandy beaches meeting clear, turquoise waters. The green vegetation surrounds several cottages set along the shoreline, with winding paths leading through the property, emphasizing the peaceful and remote atmosphere.

Villa in Anegada

4.94 out of 5 average rating, 78 reviews

Loblolly Beach Cottages: GREEN (1 bedroom/1 bath)

“Green Cottage” Caribbean cottage charm that is unique to Anegada, but now with beautiful modern amenities and a property with lots to do! Location is everything here. Step out of your cottage and into the sand at beautiful Loblolly Bay. We located on one of the most beautiful beaches and coral reefs in the Caribbean (and on most days you will have it all to yourself). Snorkeling, relaxing, walking to get a drink, stargazing, or taking an adventure tour. A private slice of heaven!

An outdoor view of the villa showcases a spacious terrace with lounge chairs and a horizon-edge saltwater pool. Surrounding mountains and the sea are visible in the background, while multiple outdoor seating areas invite relaxation.

Home in south sound

5 out of 5 average rating, 4 reviews

Secluded Waterfront Villa

Anam Cara Villa is a luxurious 5-bedroom, 6-bathroom retreat on the waterfront in Virgin Gorda's South Sound. Each en-suite bedroom features a private balcony with stunning views of the sea, marine life, and lush hillsides. The villa spans nearly 5,000 sq. ft., with a gourmet kitchen and seamless indoor-outdoor spaces. Outside, enjoy the horizon-edge saltwater pool with a swim-up bar, sunken kitchen, and multiple decks. Just minutes from North Sound's world-class dining and activities!

Top guest favorite

An open living area features retractable sliding glass doors that offer stunning views of the blue Caribbean Sea and nearby sailboats. Natural wood ceilings complement sleek concrete floors. Comfortable seating arrangements include a sofa, chairs, and a workspace, enhancing the inviting atmosphere.

Villa in Leverick Bay

4.98 out of 5 average rating, 114 reviews

Seascape Guest House, Leverick Bay, Virgin Gorda

Seascape Guest House is an exquisitely designed one bedroom villa on Virgin Gorda in the British Virgin Islands. Just completed, the spacious 650 SF villa is sustainably designed and features an open plan kitchen and living area with master bedroom and ensuite bathroom. The screened in patio and roof deck provide additional outdoor space to relax and take in the stunning ocean views. A short walk from all the amenities of Leverick Bay Resort, Seascape is a one of a kind BVI retreat.

Superhost

The expansive rooftop deck features plush synthetic grass carpeting and is adorned with comfortable outdoor furniture. A large dining table accommodates eight, surrounded by two lounge areas and a giant chess set. Retractable awnings provide shade, enhancing the space for relaxation or entertainment.

Villa in Nail Bay

4.76 out of 5 average rating, 17 reviews

1 Paradise Lane-A Modern Tropical Beachfront Oasis

Our street address is indeed 1 Paradise Lane. This centrally air-conditioned 2-BR 2.5 bath villa is situated within a lush tropical garden bordering the private Nail Bay Golf Course & the sea. Our 1,000+/- sq. ft roof top deck with glass railings is perfectly situated to capture the best sunset views and the never-ending boating traffic on the Sir Francis Drake Channel. Please note that Sunset Watch and 1 Paradise Lane share a pool and they can be rented together as a 3 BR villa.

A sparkling pool features gently sloped steps leading into the clear water. Colorful floatation device rests on the water's surface. Two separate villas are visible in the background, nestled within green landscaping under a bright blue sky.

Hotel room in Anegada

Four Diamonds Park Villas - Villa Gabrielle

Four Diamonds Park Villas consists of four separate villas each with two bedrooms, bath, living and dining areas, balcony and fully equipped kitchen. The villas are conveniently located near beaches, restaurants, and shops. They are great for individuals, couples, families or corporate stay. Each villa can comfortably accommodate four persons.The main amenities include the pool, elevated gazebo, Wi-Fi, Barbeque grill and air conditioned bedrooms.

Top guest favorite

A private deck is surrounded by lush greenery, featuring two wicker chairs with yellow cushions and a small glass table. The view showcases distant hills under a partly cloudy sky, highlighting the natural beauty of the landscape.

Home in Great Camanoe

5 out of 5 average rating, 8 reviews

Private Hilltop Villa with Boat

Enjoy our gorgeous hilltop paradise with easy access to beautiful swimming beaches, fantastic snorkeling reefs, and almost every form of water recreation imaginable. With a sweeping 280-degree panoramic view, the villa is designed to showcase the extraordinary beauty of the surrounding islands. An SUV and boat are included in the rental, ideal for exploring Camanoe and the surrounding islands.