Holiday rentals with a pool in St. John

BEST REVIEWS on the East End - HANDS DOWN!

ALWAYS BOOK with an ON-SITE LOCAL to get the INSIDE SCOOP. Book this condo to gain access to custom-made handouts to help you plan a memorable vacation! You'll love the KILLER VIEW of the Caribbean Sea about 200 feet away. This condo includes toys and games, and plenty of beach toys, noodles, and extra chairs for beach hopping! I'm frequently booked, so check out my other condos in Cowpet Bay West. airbnb.com/h/stthomasparadise10 airbnb.com/h/stthomasparadise26 airbnb.com/h/stthomasparadise42

"H2Oh What a Beach!" condo: Walk-out Beach Access!

"H2Oh What a Beach!" condo Building A of Sapphire Beach Resort & Marina: ground floor unit with direct access to one of the most beautiful beaches in the Caribbean. Steps away from Sea Salt fine dining restaurant, Sapphire Beach Bar, Paradise Pie pizza, and Beach Buzz coffee shop. A mile from Red Hook featuring many restaurants & island ferries. Great beach, swimming, snorkeling, parasailing, and relaxing right outside your door. Be among the many visitors who LOVE this totally renovated condo.

Sail Away II-WOW Beachfront to Paradise Remodeled

Sail Away II at Sapphire Beach Resort and Marina is located on the beachfront just steps away from the sparkling Sapphire Beach. The patio leads you to a dazzling infinity pool and the option of 2 immaculate beaches. Golden sand, pristine Caribbean water and amenities galore await you. No need to leave the tranquility of your room thanks to the many home furnishings within your vacation paradise. Beach level, beachfront & lush surroundings is yours to escape the hub of city life. KING SIZE BED!

House By The Sea | Idyllic Views, Pool, AC

Huis Aan Zee, “House by the Sea”, offers the perfect Caribbean getaway. Relax in your own private saltwater pool overlooking the turquoise waters of Coral Bay. This modern villa offers breathtaking views of Hurricane Hole and Drake’s Channel, blending seclusion, comfort, and convenience! *Lounge on sun chairs, soak in the pool *Enjoy AC + a fully equipped chef’s kitchen *High-speed Wi-Fi + peaceful work area for remote stays *Located minutes from St. John’s beaches, grocery stores, restaurants

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.

Seascape Villa w/ Private Pool

Discover the ultimate tropical retreat at this exclusive 3-bedroom, 3-bathroom villa, perched high above the pristine waters of St. John’s East End. Indulge in luxury accommodations complete with a fully equipped kitchen, spacious indoor & outdoor living areas, and both SOLAR power & backup generator Step out to a private saltwater pool, where you can bask in the Caribbean sun while enjoying the tranquility of this serene hideaway all just minutes from local restaurants, shops and 3 markets

Jasmine at Casa Tre Fiori

Jasmine at Casa Tre Fiori is located in the peaceful neighborhood of Fish Bay on beautiful St John. An adorable cozy private one bedroom apartment with a kitchenette, which includes a refrigerator, microwave, two burner stove. Wifi. Dish TV. AC in Bedroom with King bed. Living area AC. Private patio. Shared pool. This is a no smoking property. Adjacent rentals can be added for larger groups. See Orchid at Casa Tre Fiori, Wild Ginger at Casa Tre Fiori and Cactus Flower Cottage.

Skytop Studio~Next to Hiking Trail~New Pool

Modern 1 bedroom apartment In Fish Bay Skytop with Hillside View of the National Park, fully equipped kitchen, Saatva Loom & Leaf memory foam mattress. The property is right next to the National Park Great Sieben Trail, which connects to several major hiking trails. Cruz Bay, Grocery Stores and restaurants are 12min drive away. Klein Bay a beautiful Private rocky beach great for snorkeling is 4 min drive away. Shared brand new Pool with two other apartments. Shared BBQ by the Pool.

Periwinkle Cottage in Coral Bay w/Pool, and Views🏝

Periwinkle Cottage of Coral Bay is a perfect rendition of a traditional West Indian cottage with modern amenities. Ceiling fans, large screened in porch and open air porch areas. Located at the end of a private road, Periwinkle has a Million Dollar view of Coral Bay! Located only minutes from grocery stores, shopping & dining in Coral Bay. This cottage offers privacy & sits on over a half acre lot! If you need a Jeep while you are on St John, we rent out our 4 door Jeep Wrangler

Rockroom One Bedroom Condo at The Hills Saint John

"The Rockroom" is a one bedroom apartment located within The Hills Saint John. This large space with amazing views of Cruz Bay and St Thomas features a large bedroom with King bed, two full baths, a large living area and a full kitchen. There is also a large private patio with a gas grill and patio furniture. Guests staying at Rockroom will also have access to The Clubhouse Bistro (open seasonally and located on the property) as well as a 24 hour fitness center and community pool.

Peaceful 1 bed/Lush gardens/Plunge pools

Experience ocean views, AC-cooled comfort, solar power and a spacious deck in this new solar-powered cottage. Part of a unique collection, it shares an infinity waterfall plunge pool with "Caribbean" cottage (two more cottages coming in 2026). Enjoy constant breezes, afternoon shade, and magical moonrises from the “Ocean” cottage. Guests have 24/7 on-site concierge service and assistance, with full vacation planning by a Superhost experienced in welcoming first-timers to St. John.

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.