Family-friendly holiday rentals in Anna's Retreat

Book Now! Caribbean Sunshine! Amazing Views!

Book Now! Down Island Dream is a 1BR/1BA luxury villa @Point Pleasant Villas on the East End of St Thomas. 2 Restaurants, 3 pools, nature trail & a small intimate beach to enjoy. Your vacation home/5 minutes to Red Hook w/shops, bars, restaurants & the ferry to St John where you can explore, hike & enjoy our National Park Beaches! 3 mins to Lindquist & Coki beaches. Amazing views & refreshing breezes await you at Down Island Dream! Try our home away from home for the week & fall in love!

Killer View; Book w/a Local for the Inside Scoop!

Check out my reviews - Top Tier Service from the Local St. Thomian! Sherri has lived in St. Thomas for 20+ years! JUST 200 FEET to the BEACH, Kid Friendly, Gated Community w/ Parking. On the BEACH: 2 Restaurants, lounge chairs, pool, & hot tub, 2 bars, & beach toys to rent. Within MILES: Ferry to nearby islands, Restaurants, Charter Boats, Grocery stores, Banks, Boutiques, Jewelry, Postal service, Pharmacy, Medical care, & more. ASK for Sherri's Custom Handouts including her BEACH GUIDE

Traveler's Hideaway

Come enjoy this quiet, cozy, air conditioned 2 bedroom 1 bath rental space with stunning mountain views. Wake up to fresh, cool, calming breezes compliments of world famous Magen's Bay which is only a 5 to 7 minutes drive away. Apartment comes with its own entrance, kitchen and living area and caters to all, from a single traveler, couples, friends or a small family with children. Amenities include high speed internet and TV. Located within a 10 minutes drive to downtown Charlotte Amalie.

(Upper Level) Peaceful Getaway in Frenchman Bay

Indulge in the serenity of our Rock City retreat, where breathtaking ocean views meet refined comfort. Enjoy the patio, WiFi, AC, and eco-friendly solar energy. Ideally situated for families and travelers alike, our haven is close to Morningstar Beach, Westin conferences, and Havensight shopping. For added convenience, rent an SUV or utilize taxi services. Click on our Group Villa listing which offers ample space for up to 15 guests. For a seamless stay, review listing details and house rules.

Hillside Hideaway

Perfect getaway for an island getaway, business, or solo adventuring. This well appointed one bedroom apartment is nestled in a quiet central hillside neighborhood with views of Hans Lollik, Jost Van Dyke, and Tortola islands. Conveniently located one mile from Magen's Bay and ten minutes to downtown Charlotte Amalie by car. Rental car is a must! Come enjoy the tranquil views, take a dip in the pool, and experience St. Thomas like a local. Please read all listing details and house rules.

Tropical Modern Loft | SoHo Style | Concierge

Single night bookings welcome! A luxe art loft experience in the heart of St. Thomas, this exclusive space in a convenient central location provides a chic home base, with sleek design, concierge options, + creative vibes. Perfect for both adventure and serenity. Ample space to lounge, with a balanced historic/contemporary aesthetic, and near beaches, restaurants, historic landmarks, boutiques, + ferry/airport/transportation. Private gated parking and a cafe and art gallery right downstairs.

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.

NEW WATERFRONt Villa at Magens Bay, hot tub, Jeep

This new waterfront villa is conveniently located steps away from the Platform beach and 5 min. drive to famous Magens Bay Beach. Enjoy morning coffee watching turtles or Eagle rays flying above the turquoise water right from your balcony. This extraordinary furnishing and modern feel will provide cozy and exceptional vacation for your family and friends. The outdoor space offers great relaxing area overlooking the Caribbean sea. Hot tub brings the resort feel with the privacy you deserve.

Stylish & Luminous 2BR-spectacular water views!

Welcome to a newly renovated 1,800 sq foot 2 bedroom located in the heart of historic Charlotte Amalie! Our space is perfect for travelers who wish to experience the beauty of the US Virgin Island. Each room is oversized, with tall ceilings, and boasts stunning panoramic views of the Caribbean that are sure to take your breath away. The space is as stylish as it is comfortable, with modern furnishings and luxurious touches throughout, yet contextually appropriate for the historic setting.

2BR/2BA AMAZING MagensBay View! SerenityNorthstar⭐️

Solar-Powered Luxurious 2BR w/breathtaking views of Magen’s Bay. Serenity Northstar is located in the Northside area of St. Thomas near Sibs, Mafolie Hotel, and Mountaintop. Full Air conditioning. Rent a car and live like a local. Short drive to famous Magens Bay Beach; Less than 10 min from shopping, dining, bars, etc. Includes SmartTVs with Netflix etc. 2 rms w/ King beds. Queen sofa-bed also included. 1 Rollaway cot. Sleeps up to 6ppl. Laundry. Private Parking. Patio. Killer views!

Sieben Apartment * Pool* next to Hiking trails

Sieben is a spacious 2 bedroom, 2 bathroom apartment with fully equipped kitchen and washer/dryer. Both bedrooms feature memory foam mattresses. Primary bedroom has a king bed with private en-suite bathroom. Second bedroom can be set up as two twin beds or one king. Smart TV with Netflix and streaming apps (no cable). 10 min drive to Cruz Bay, restaurants, and grocery stores. 25 min drive to North Shore Beaches. 4 ft shared pool with two other apartments and shared BBQ by the pool.

Private Pool in Paradise! Ocean View Steps 2 Beach

Come enjoy the island life at this tranquil villa with private pool...only steps from the beach! Cooler, snorkeling gear, and beach chairs INCLUDED! The entire home has been remodeled. The pool has been fully updated as well as the deck area, which includes brand new furniture and high-end loungers. A new gas grill has also been added for your outdoor grilling pleasure. Stream all your favorites with our strong Wi-Fi. Upscale restaurant, Pangea, is just steps away. Free parking.