
Guesthouse holiday rentals in Anna's Retreat
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Top-rated Guesthouses in Anna's Retreat
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

Garden Suite at Sapphire Beach Retreat
Very comfortable guest suite with direct access to Sapphire Beach. The garden suite boasts a queen bed in the main room and 3 twin beds in the bunk room... 2 bunks and a trundle. The Suite has a refrigerator, microwave and coffee maker. In addition, there is a private patio for your enjoyment. The location is premium. The home is just 5 minutes from Red Hook. You'll enjoy the ability to walk unto Sapphire Beach and enjoy all of Sapphire's offerings... coffee shop, restaurants and bars.

Oceanfront Clifftop Escape Guest Suite
Maridadi Clifftop is perched atop Boatman Point, offering sweeping, south-facing views, and is located just under a 10-minute drive (2 miles) from Cruz Bay. The clifftop boasts a stunning outdoor terrace perched just above the crashing waves, surrounded by lush tropical vegetation. Inside, a modern, air-conditioned unit features a king-size bed, smart TV, ceiling fan, his and hers nightstands, a walk-in closet, a full bathroom, and a living area, creating the perfect romantic Caribbean escape.

Take your Breath Away Views Upper Cottage
OUTSTANDING views of BVI's, ST John & Caribbean Blues! Spacious, tranquil & breezy Cottage perched on the top of Harmony Hill! Newly remodeled with YOU in mind & all the comforts of home. Privacy, million dollar views from all rooms, designated office/work area and 2 private decks and abundant closet spaces for all your needs. Indoor & outdoor dining. Centrally located on island & less than 10 min Magen's, Coki, Lindquist, Sapphire Beach. Take it easy at this unique and tranquil getaway.

Sunrise Cottage - Secluded, Romantic, Private
Sunrise cottage is located on the cool & breezy north side of St. Thomas. A relaxing 1 bedroom cottage with a full kitchen & living area. You can soak up the sun on the sundeck or hang out in your private soaking pool, while appreciating the breath taking view during the day & the abundance of stars at night. When venturing out you are 20 mins to Magen’s Bay Beach, 15 mins to Town, 30 mins to Red Hook. Note: The hosts live on property with 2 dogs and this cottage is adult only 18 or older.

Darling Palms: Solar Tree House Studio
Solar powered, battery back up! Our spacious studio apartment is nestled among a paradise of palm trees, with a ‘tree house' atmosphere. Just a short stroll away, discover the allure of a nearby beach and resort, offering two restaurants, a market, and a pool bar for ultimate relaxation. Embrace the outdoor ambiance on our patio, complete with comfortable seating and a grill, perfect for alfresco dining. Please note that the studio shares a wall with another rental unit. Parking available!

Faith
Forget your worries in this spacious and serene space. Enjoy outdoor kitchen and dining area in Faith Cottage. Relax in the shared space that makes up Grateful Grotto Gardens. Our one bedroom/ one bathroom cottage is all you need after a day at the beach. Centrally located off of Centerline Road, Minutes from Cruz Bay and less than 20 minutes from Coral Bay. You can feel at peace in the safe and homely residential setting and enjoy a comfortable and restful nights sleep in Grateful Grotto.

OMAJELAN CASTLE (A)
Welcome to the Omajelan Castle. Set amongst the lush mountain canopy of Santa Maria, on the North Western side of St. Thomas, with a view that is befitting of a king and queen. About 5 minutes from the beach and 15 minutes from downtown, Charlotte Amalie, The Omarjelan Castle's regal architecture is further enhanced by a breathtaking yet tranquil view of the Atlantic ocean. These small yet comfortable efficiencies afford you a unique experience you'll not soon forget

Incredible Views!- Solar Power- 5 min to beach!
- You’ll have a private newly renovated apartment (middle level) that sits within the jungle high up on the mountain side. - Views of Charlotte-Amalie Harbor, St Croix, and a glimpse of St John. - 5 minute drive to Hull Bay and the best fish tacos on the island. Magens Bay is just 10 minutes away. - Starlink internet so you’ll never lose internet! - House complex is powered by solar panels and back up batteries!

St John villa 7min to Cruz bay, Oceanview, King Bd
This charming villa is conveniently located just 7 minutes from Cruz Bay, offering easy access to restaurants, a grocery store, and beautiful beaches. Situated on a steep hill and on the second floor, the home provides spacious accommodations perfect for a family of four, with both queen and king-size beds and a full bathroom. Guests will also appreciate the added perks of free parking and WiFi during their stay.

La Brisa: Peaceful Oceanview Retreat
Escape to La Brisa, a serene oceanview retreat perched 1,100 feet above sea level on Skyline Drive. This luxurious one-bedroom suite offers breathtaking Caribbean views, modern coastal decor, and thoughtful amenities for a tranquil island getaway. Perfectly located near Magens Bay and vibrant Red Hook, La Brisa is ideal for relaxation, exploration, or a romantic escape. Your paradise awaits!

The Guest House of Villa Solare
Upon entering the Villa property, you experience the natural Caribbean artistry of stone & shell archways, brick courtyard and tropical gardens. This accommodation includes access to the upper level of the Guest Cottage with a queen suite (en-suite bath) and attached, separate room with kitchenette, sleeper sofa and second full bath.

Cactus Flower Cottage
Beautiful Cactus Flower Cottage overlooking Fish Bay and the Caribbean. Hike directly out of Fish Bay to the most well known National Park Reef Bay Trail, L'Esperance Trail, Fish Bay Gut, etc! Hikers delight. Close to Cruz Bay. Beautiful, peaceful and friendly area of St John. Quick drive to Cruz Bay and the North Shore Beaches.
Popular amenities for Anna's Retreat guesthouses
Family-Friendly guesthouses

Coconut Coast Villas - Three Bedroom Suite (Bird of Paradise / Bougainvillea)

Coconut Coast Villas - Three Bedroom Suite (Hibiscus/Alamanda)

Coconut Coast Villas - Hibisuc Two Bedroom Waterfront Suite

Coconut Coast Villas - Bougainvillea Waterfront Studio
Guesthouses with a patio

Two Tickets To Paradise Cottage -Tiki Bar & Pool

Hope

2 Bedroom Cottage, with pool.

Charlotte Amalie Overlook Soursop Room5-3

Charlotte Amalie Overlook Ackee

Darling Palms Retreat: Solar Beachside 2BR Oasis

Charlotte Amalie Overlook Papaya Room5-2

Beautiful & Spacious Guest House w/ Gym
Guest house rentals with a washing machine and dryer

La Brisa: Oceanview Escape w/ Included Jeep Rental

Coconut Coast Villas - Petrea Waterfront Studio

Crown Mountain Manor. Modern Living with a view.

Estate St. Peter Guest House w/ maid

Blue Aweigh

Coconut Coast Villas - Alamanda Waterfront Studio
Quick stats about guesthouse rentals in Anna's Retreat

Nightly prices starting at
Anna's Retreat holiday rentals start at $77 AUD per night before taxes and fees

Verified guest reviews
Over 30 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Anna's Retreat rentals

4.8 Average rating
Anna's Retreat stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Cottage rentals Anna's Retreat
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- Rentals with a patio Anna's Retreat
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- Rentals with a washing machine and dryer Anna's Retreat
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