Vacation rentals in Loblolly Bay

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Loblolly Bay

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

0 of 0 items showing

1 of 3 pages

Top 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.

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 lush garden area offers a view of the turquoise sea and sandy beach beneath a partly cloudy sky. Green foliage and colorful flowers frame the scene, creating a vibrant contrast against the water's varying shades.

Apartment in Road Town

4.89 out of 5 average rating, 232 reviews

Trunk Bay Spring - downstairs self-contained room

Hi! We paused this listing after being badly damaged by Hurricane Irma, and then due to Covid 19, but we're back – repaired and upgraded! The outdoor shower that our guests loved is still there, only now it has hot water. There's also a new kitchen made of hardwood we were able to salvage after Irma. Great news! The beach is still there, too, and still a just ten minute walk away. Always popular for being simple and beautiful in a fantastic location, now it's the same, but even better!

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!

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.

Guest favorite

A spacious pool area is surrounded by lounge chairs, with lush greenery and hills in the background. The pool features distinct sections, including a shallow area. Bright blue skies and scattered clouds add to the inviting atmosphere.

Apartment in Tortola

4.95 out of 5 average rating, 20 reviews

Orchid Bloom pool/beach nest

Orchid bloom is privately owned nestled on the premises of the magnificent Wyndham Resort Hotel on Lambert Beach. This unit boast a comfortable, private, first floor, garden view, poolside side apartment. Fine dining Restaurant on premises as well as, gym in a picturesque environment which lends itself to relaxation and rejuvenation. Just ten minutes drive from the airport, with magnificent hill and ocean views. Make Orchid Bloom the place for your next BVI vacation.

Guest favorite

An inviting plunge pool is situated on a wooden deck, surrounded by lush greenery and offering panoramic views of the turquoise waters below. The horizon showcases distant islands under a bright blue sky dotted with fluffy clouds.

Villa in Brewers Bay

4.86 out of 5 average rating, 70 reviews

Villa Matija

Villa Matija is nestled comfortably into the hillside overlooking Brewers Bay on Tortola in the British Virgin Islands. Allow yourself a little luxury and be eco-friendly at the same time! Villa Matija (pronounced ma-TEE-ya) sits above Brewers Bay with an outstanding view of Jost Van Dyke and several other smaller cays & islands. On a clear day you can see Puerto Rico (about 70 miles away)!

Superhost

A spacious bedroom features a large king-size bed with crisp white linens and a decorative throw. Soft natural light fills the room through a window adorned with sheer curtains, while a bedside lamp provides additional illumination. A small seating area is also visible.

Hotel room in Leonards

4.82 out of 5 average rating, 17 reviews

Cozy Beach Front Room In Cane Garden

Welcome to ELM Beach Suites in Cane Garden Bay! Our little slice of paradise is right on the beachfront, where you can hear the waves crashing on the shore right from your room's balcony. Special Offer: Get 20% OFF: Book 5+ nights in October to get 20% off your stay. Book anytime from August 1 and September 30 2025, and get our 100% refund guarantee for bad weather cancellation.

Guest favorite

A small, charming shack is nestled among large boulders, showcasing a wooden deck with seating. Light blue shutters frame the windows, allowing natural light to enter. Lush greenery surrounds the structure, while the sky is a bright blue with scattered clouds.

Hut in Tortola

4.95 out of 5 average rating, 168 reviews

Tiny Cozy Shack 8 minutes from Beef Island airport

Located in a breezy valley on the East End of Tortola overlooking Beef Island & Virgin Gorda. Nestled among boulders where you can enjoy the sun rise. Simple tiny room (8’x10’) with full size bed has a private bathroom + outdoor shower, no hot water.. Outdoor kitchenette with mini fridge, stove, kettle, toaster. Electricity, solar lights and WiFi available.

Guest favorite

A covered deck presents a large wooden dining table surrounded by mismatched chairs, offering panoramic views of the turquoise waters and nearby islands. The serene atmosphere is complemented by soft clouds drifting overhead and the expansive horizon.

Home in Tortola

4.94 out of 5 average rating, 150 reviews

Private One Bedroom Villa, HotTub, Amazing Views

Nestled on top of Cooten Bay in Tortola, British Virgin Islands, Cooten House has amazing views that will take your breath away. Whether you are looking for a romantic getaway, a place to relax and soak up the sun or all of that plus close proximity to great surfing spots, Cooten House will exceed your expectations.

Top guest favorite

An outdoor area features a private pool surrounded by a deck with lounge chairs. Lush greenery and rocky landscaping create a natural setting, while the two-story house offers large glass windows that showcase scenic views of the hillside.

Villa in Wesley Will

5 out of 5 average rating, 51 reviews

Villa Naku, escape and relax.

Naku is a fantastic place to escape the hustle and bustle and really get back to nature. We are developing our guide book, but we have extensive knowledge and friends on island , so please let us know what your interests are and we will do our best to help. Please enjoy and let yourself escape.

Guest favorite

A spacious studio with a ceiling fan and a cozy bed near large windows offering ocean views. A kitchen area features a stove and a dining space with green chairs. Light-colored walls and natural materials create a bright and airy atmosphere.

Cottage in Virgin Gorda

4.98 out of 5 average rating, 48 reviews

Cachette Cottage - Studio Villa/private pool

Part of the larger villa, La Cachette, the Cottage can be rented separately for only two people. You have a private entrance, private pool, and plenty of privacy from the main house. Located on the Atlantic side of the island you get great breezes and beautiful sunrises.