Cottage holiday rentals in Anna's Retreat

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Top-rated cottage rentals in Anna's Retreat

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Top guest favourite
Cottage in Cruz Bay
4.91 out of 5 average rating, 118 reviews

SKIPPER COTTAGE unit number 1

Skipper is a stand alone cottage: a large 450 sq ft efficiency with 50 sq ft deck. Queen bed, mattress is a Marriott Silver Beauty Rest & full futon along with full kitchen & shower bathroom. The property is all fenced for Skipper, my Portuguese Water Dog. Skipper was the captain of our boat Skedaddle. The yard is very lush & green, seems like a mini rain forest in town. Our place is 'old' Caribbean, wooden cottages, no concrete. Skipper & Skedaddle are two identical cottages next to each other.

Superhost
Two director's chairs with vibrant yellow fabric displaying tropical floral patterns are positioned at a kitchen island. The warm wood of the cabinetry is visible in the background, enhancing the cheerful and inviting setting within the kitchen area.
Cottage in Charlotte Amalie
4.79 out of 5 average rating, 38 reviews

Island Life in Frenchtown, Centrally Located

We welcome you to the most authentic ISLAND LIFE that we hope you will fall in love with. Being on a hill, enjoy balmy breezes when you open your windows while also letting the charm of Frenchtown in. Wake up to church bells ringing on a Sunday morning; spy the seaplane landing in the bay; enjoy dinner on the patio with supplied amenities for cooking; walk to bars, restaurants & downtown shopping; take a $1 Safari bus to the beach; pack lightly knowing that we have thought of everything for you!

Top guest favourite
The bedroom features a spacious bed with a light-colored blanket, complemented by wooden furniture, including a nightstand and wardrobe. Natural light enters through multiple windows, illuminating the room with a serene ambiance. A rustic decor adds charm, while a pet dog rests on the floor.
Cottage in Central
4.99 out of 5 average rating, 166 reviews

Caribbean Style Cottage

The 500sq. Tortuga Cottage is located in Fish Bay, St. John in the US Virgin Islands. The property is privately owned and adjacent to the National Park. This charming cottage places you within a 5 minute walk to Reef Bay beach and gives you access to many of St. John's greatest hiking trails. By car, we are 3 miles from town (Cruz Bay), where you will find all of your necessities. This is the ideal cottage for a couple or two friends. We have a full kitchen, a king Casper mattress, and much more

Guest favourite
A cozy screen porch features a swinging chair and a round dining table set for four. Surrounded by lush greenery, a coffee table with a decorative wooden design sits nearby. Natural light filters through the screens, creating a serene atmosphere.
Cottage in Carolina, St. John
4.96 out of 5 average rating, 46 reviews

Verde Cottage (2BR/1BA) Peaceful Rainforest Oasis!

Nestled in the rainforest down a long stairway fringed with tyre palms and tree orchids, a newly remodeled 650 sqft Cottage sits enveloped by virgin St John flora and fauna. The main living areas and bedrooms are all tastefully appointed and fully air-conditioned. The efficiency kitchen is well-equipped. The large wraparound screen porch provides indoor/outdoor living with cozy seating and dining 'al fresco'. Welcome to the Verde Cottage - your peaceful island getaway on Bordeaux Mountain!

Top guest favourite
An outdoor patio features tiled stones surrounding a small salt-system plunge pool. Two lounge chairs with cushions are positioned nearby, while lush green banana plants fill the background. A beige umbrella provides shade, and the sky is bright with scattered clouds.
Cottage in Coral Bay
4.99 out of 5 average rating, 138 reviews

Sweet Spice: A Nifty Little Cottage. With A Pool!

This very small 1 BR cottage lives BIG with a screened porch, SOLAR POWER, valley views, ac, dishwasher, outdoor fitness, and plunge pool. With a clean modern vibe, Sweet Spice is more laidback getaway than luxury villa. It’s an ideal HQ for 2 active STJ adventurers - but with a few extra amenities! Located off the beaten path on the quiet side of STJ, it feels secluded but is only a 5 minute drive to the shops of Coral Bay. Note: road is rough and requires a 4WD and there are LOTS of stairs.

Guest favourite
A round table is set on a patio overlooking the ocean, adorned with a vibrant bouquet of orange flowers in a clear vase. Sunlight glistens on the water, while shaded cups and a sun hat rest on the table, highlighting a serene outdoor ambiance.
Cottage in Northside
4.92 out of 5 average rating, 37 reviews

Serenity Breeze: Ocean View Retreat

Welcome to Serenity Breeze, your island paradise nestled in the heart of Peterborg. - 1-bedroom retreat with stunning ocean views - Tranquil atmosphere enhanced by cooling trade winds - Air conditioning for ultimate comfort - Breathtaking sunsets to enjoy every evening - Spacious design that promotes relaxation - Experience the tranquility of island life at Serenity Breeze. - Close to Magen's Bay Beach and vibrant dining in Charlotte Amalie and Red Hook

Guest favourite
The entrance to the cottage is framed by lush tropical plants and palm trees, creating a vibrant atmosphere. A decorative stone archway leads to a white door with a glass panel, which is set against warm orange exterior walls.
Cottage in Saint John
4.95 out of 5 average rating, 21 reviews

Private, Perfect for Couples Retreat-Ocean Views

Nestled on St. John’s spectacular South Shore, this tastefully decorated one-bedroom cottage is the ideal home-away-from-home island getaway! Solar panels and back up batteries to fully power the house. The bedroom features a King bed, A/C, & flat-screen TV. The kitchen features granite countertops, stainless steel appliances & island with seating for 4. The cozy living area has A/C, comfortable seating, flat screen tv, dvd player & Bose surround sound speaker.

Guest favourite
A serene pool area is depicted with a clear turquoise pool reflecting the sky. A graceful statue stands nearby, enhancing the tranquil setting. The distant view of the harbor is visible under a partly cloudy sky, framed by a decorative railing and outdoor seating.
Cottage in Northside
4.9 out of 5 average rating, 102 reviews

Caribia Cottage-Elegant Villa w/Private Pool

Caribia Cottage is located in a private Estate with access only through an electronic gate. The spectacular panoramic view of the St. Thomas Harbor is unforgettable and one which many a famous star toasted to when the property was formerly owned by a celebrated Broadway Producer. Walk just two steps from the Cottage into the spacious swimming pool. Enjoy gazing at the busiest Harbor in the Caribbean, as the mega yachts, seaplanes and cruise ships come and go.

Guest favourite
The cottage is set within a vibrant garden, with lush tropical plants and colorful shrubs surrounding the property. Tall palms provide shade, while a covered patio is visible through the greenery. A gated entrance adds a sense of privacy to the peaceful setting.
Cottage in Cruz Bay
4.92 out of 5 average rating, 37 reviews

Seabreeze Cottage with private pool in Cruz bay

The cottage is conveniently located two minutes to the town of Cruz bay and five minutes to National Park. It’s surrounded by lush landscape and gated property. The cottage is fully AC, covered patio, a private pool, outdoor bbq covered patio. AN ENTIRE COTTAGE BACK UP GENERATOR FOR POWER OUTAGES one of a few offer on the island. It will be helpful when the grid goes down of which occurs quite often. You can still have the comfort without any interruption.

Top guest favourite
A charming studio home, surrounded by lush greenery, features a welcoming porch with steps leading to the entrance. Stone pathways are lined with various plants, complemented by seating areas designed for relaxation. The building is highlighted by large windows that invite natural light.
Cottage in Cruz Bay
4.98 out of 5 average rating, 95 reviews

Sol~Azul Cozy Studio Cottage w/ Pool & Ocean View

Fully equipped, spacious studio with full kitchen. Beautiful view of the sea and St Thomas in a peaceful neighborhood near Cruz Bay. Easy to navigate roadways with flat driveway and plenty of parking. Enjoy a nice evening on the pool deck to watch the sunset. Conveniently located 10 min from beaches and shopping. Beach Chairs & Towels provided. Laundry on-site. Shared Grill and Pool area w/ the Main Villa on property. Perfect for a couples getaway.

Superhost
The cottage is surrounded by lush greenery, featuring a striking orange metal roof. The exterior includes several windows and a porch area shaded by vibrant tropical plants, creating a serene and natural setting amidst the mountain landscape.
Cottage in St. John
4.86 out of 5 average rating, 106 reviews

Coral Bay Farm Cottage

Enjoy paradise with this beautiful, newly remodeled cottage as your home away from home. This gem shares the same property, and overlooks, the only organic farm on the island. The farm produces all of the local salad greens, vegetables, herbs, and fruits for all the best restaurants and grocery stores. If you are planning on cooking at the property, let us know and we will bring you some fresh produce.

Top guest favourite
A wrap-around balcony features a round table with a glass of a refreshing drink. A comfortable lounge chair is positioned for optimal views of the lush greenery and serene bay. The distant hills and blue sky create a peaceful backdrop.
Cottage in Cruz Bay
4.87 out of 5 average rating, 71 reviews

Two Bay View: Perfect for a private getaway

Two Bay View is an octagonal cottage set on three private acres between Great Cruz Bay and Chocolate Hole. The home offers both privacy and convenience to Cruz Bay (approximately 2 mile drive). Facing north-east on St. John's north side, it gets the famous trade-wind breezes nearly all year long. The cottage has an 180 degree view with expansive decks on the two upper levels.

Popular amenities for cottage rentals in Anna's Retreat