
Guesthouse vacation rentals in Anna's Retreat
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Anna's Retreat
Guests agree: these guesthouse rentals 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.

Peaceful Island Retreat with Stunning Bay Views
You'll have a great time at this comfortable place to stay. Enjoy the trade wind breeze and the sunrise over Fish Bay from the covered porch of your own private cottage. Ayiti cottage is an east-facing cottage located in a quiet Fish Bay neighborhood, an easy 2.9 miles from Cruz Bay and 20 minutes away from the stunning north shore beaches. Ayiti cottage is perfect for any couple that needs a quiet and private escape to enjoy the beautiful island of St. John! We are a non-smoking property.

Two Tickets To Paradise Cottage -Tiki Bar & Pool
Welcome to Two Tickets To Paradise Cottage. The coolest place to stay on St Thomas. Enjoy a quiet piece of paradise and live like a local. Our beautifully renovated cottage, pool & bar has everything you need to relax or party. Solar & Tesla batteries keep the power on. The saltwater pool is refreshing at your own private tiki bar. Honor bar, 55" tv and bluetooth surround sound. Red's Rum Roost is island famous and has it's own t-shirt. The owner is a retired Hilton Hotels sales manager.

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

La Brisa: Oceanview Escape w/ Included Jeep Rental
Escape to La Brisa, a luxurious oceanview suite perched 1,100 feet above sea level on Skyline Drive. Enjoy breathtaking Caribbean vistas, modern coastal decor, and exclusive use of a 2019 AWD Jeep Compass for exploring the island. With thoughtful amenities and a serene location near top attractions, La Brisa offers the perfect blend of adventure and relaxation for an unforgettable stay. ***MUST BE 25 YEARS OLD TO BOOK.***

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.
Popular amenities for Anna's Retreat guesthouse rentals
Family-friendly guest house rentals

Faith

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

Cactus Flower Cottage

Sweet Cottage.

Oceanfront Clifftop Escape Guest Suite

Coconut Coast Villas - Hibisuc Two Bedroom Waterfront Suite

Sunrise Cottage - Secluded, Romantic, Private

Coconut Coast Villas - Three Bedroom Suite (Bird of Paradise / Bougainvillea)
Guest house rentals with a patio

Oceanview 4BR Villa w/King Suite 7 min to Cruz Bay

Darling Palm: Solar Beachside Guesthouse

Petite Pardis

Seaside Studio Cottage with Boulder Beach Access

Hope

2 Bedroom Cottage, with pool.

Darling Palms Retreat: Solar Beachside 2BR Oasis

Sea the View Room 305
Guest house rentals with a washer and dryer

Cottage Adore

Blue Aweigh

Charlotte Amalie Overlook Ackee

Charlotte Amalie Overlook Soursop Room5-3

Charlotte Amalie Overlook Papaya Room5-2

Coconut Coast Villas - Petrea Waterfront Studio

Estate St. Peter Guest House w/ maid

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

Nightly prices starting at
Anna's Retreat vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 30 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, 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
- Punta Cana Vacation rentals
- San Juan Vacation rentals
- La Romana Vacation rentals
- Bayahibe Vacation rentals
- Juan Dolio Vacation rentals
- Carolina Vacation rentals
- Sainte-Anne Vacation rentals
- Culebra Vacation rentals
- Saint Thomas Vacation rentals
- Saint Croix Vacation rentals
- Aguadilla Vacation rentals
- Basse-Terre Island Vacation rentals
- Fitness-friendly rentals Anna's Retreat
- Condo rentals Anna's Retreat
- Rentals with outdoor seating Anna's Retreat
- Rentals with beach access Anna's Retreat
- Cottage rentals Anna's Retreat
- Rentals with pools Anna's Retreat
- Apartment rentals Anna's Retreat
- Rentals with a patio Anna's Retreat
- Rentals with a hot tub Anna's Retreat
- Rentals with a washer and dryer Anna's Retreat
- Family-friendly rentals Anna's Retreat
- Guesthouse rentals Saint Thomas
- Guesthouse rentals U.S. Virgin Islands
- Flamenco Beach
- Honeymoon Beach
- Limetree Beach
- Magens Bay Beach
- Cane Garden Beach
- Coki Beach
- Cinnamon Bay Beach
- Cane Bay Beach
- Secret Harbor Beach
- Peter Bay Beach
- Josiah's Bay
- Virgin Islands National Park
- Maho Bay Beach
- Sugar Beach
- Coral World Ocean Park
- Isla Palomino
- The Baths
- Sun Bay Beach
- Cane Bay
- Brewers Bay Beach
- Cond Marina Lanais
- Lindquist Beach
- Point Udall
- Paradise Point Tranway




