Vacation rentals in Josiah's Bay

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Top-rated vacation rentals in Josiah's Bay

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Top guest favorite

A tranquil beach scene features soft white sand bordered by calm turquoise waters. Beach chairs are positioned under swaying palm trees along the shoreline. A row of modern condos is set on a hillside, with their balconies overlooking the peaceful Caribbean Sea.

Condo in East End

5 out of 5 average rating, 67 reviews

Family Friendly, Killer View, Pool/HotTub

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

Guest favorite

A view of the sparkling blue waters is framed by the balcony railing, showcasing boats gently bobbing in the bay. The sunlit scene features lush greenery and distant buildings, creating a serene coastal atmosphere.

Condo in East End

4.93 out of 5 average rating, 27 reviews

Hummingbird Haven - Beachside condo on Cowpet Bay

Pictures do not capture the beauty surrounding this space. Come visit, experience waking up to breath taking views, admire stunning sunsets, walk or swim in the white sandy beach, relax by the pool, or simply forget your worries in this spacious three bedroom & three-bathroom beach condo. We are located in one of the most desirable areas of the island, Cowpet Bay East. Hummingbird Haven is an affordable Caribbean dream vacation Condo to share with your family and friends. All you need is here!

Guest favorite

The image displays a panoramic view of a beach cove surrounded by lush greenery and hills. Crystal-clear turquoise waters are dotted with sailboats, while a sandy shoreline extends along the coast. The scene captures a serene and tranquil Caribbean landscape under a clear blue sky.

Condo in East End

4.91 out of 5 average rating, 226 reviews

Luxury Beachside Escape with private pool and wifi

This villa was just renovated and is absolutely amazing, plus no one can see you in our private pool or patio. Stunning views of the pool and palm trees throughout the villa. New kitchen and bathroom with luxury finishes, this beachside escape is a short walk to Sapphire beach and Lindquist beach which are two of the best beaches in the Caribbean. New king mattress, new 55" TV, Cable, DVDs, great furniture, amazing shower with garden and so much more. We promise you will absolutely love it!

Superhost

A large outdoor pool area is surrounded by palm trees and lounge chairs. A decorative stone fountain featuring a pineapple motif sits at the center of one pool, with clear blue water reflecting the sunny sky above. The spacious layout allows for both relaxation and recreation.

Condo in East End

5 out of 5 average rating, 3 reviews

Walk to Coki Beach! POOL - Remodeled 3BR Condo

Welcome to Pineapple Village 3308, your beautifully remodeled condo on St. Thomas located in the heart of Margaritaville. With beach access, an unbeatable location, and plenty of room for the whole family, this vacation rental on St. Thomas offers everything you need for a Caribbean escape filled with fun, relaxation, and adventure. Traveling With a Bigger Group? We’ll show you additional nearby rentals so your whole crew can stay close and enjoy all the perks Pineapple Village has to offer.

Guest favorite

A spacious living area is illuminated by natural light, featuring a large sectional sofa adorned with patterned cushions. Two round ottomans are positioned on a geometric-patterned rug, while a sleek entertainment unit displays various decorative items and a television, complemented by ceiling fans for comfort.

Villa in East End

5 out of 5 average rating, 35 reviews

Amazing Pineapple Village Villa in Margaritaville

Escape to the ultimate tropical getaway within the legendary Margaritaville Resort on the picturesque east end of St. Thomas in the US Virgin Islands. Here, you will discover the epitome of elegance in this newly remodeled 3-bedroom, 4-bathroom condo. Featuring a shared pool and privileged access to resort amenities, this residence offers a harmonious blend of luxury and leisure. This meticulously curated space ensures every aspect of your vacation is nothing short of perfection.

Superhost

Condo in East End

4.87 out of 5 average rating, 104 reviews

Paradise Beach Haven with Spectacular Ocean Views

The great thing about this place is, that is right on the beach,plenty shade by the seagrape trees, and palm trees, snorkeling right outside the patio as well swimming, kayaking, and plenty activities, marina to rent boats or take excursion is right there as well, restaurants and dining, great views, nightlife, and family-friendly activities. You’ll love my place because of the comfy bed and the coziness, the easy in and out to the water for swimming or snorkeling. free *wi/fi

Guest favorite

Home in East End

4.98 out of 5 average rating, 50 reviews

Island Daze - Amazing Views

Welcome to our Caribbean paradise perched atop the picturesque Point Pleasant hillside! Our stunning 1-bedroom, 1-bath villa is the perfect escape for up to 4 guests, promising a vacation of serenity and adventure on the enchanting island of St. Thomas. The centerpiece of the living area is an extra-large sectional sofa that comfortably sleeps 2, perfect for unwinding after a day of exploring the island. Don't miss out on to experience Caribbean luxury at its finest.

Guest favorite

A sandy beach stretches along the shoreline, with crystal-clear turquoise waters gently lapping against smooth rocks. Lush greenery and distant palm trees create a tranquil backdrop. Sunbathers and swimmers can be seen enjoying the clear skies and warm sun, enhancing the serene beach atmosphere.

Apartment in East End

4.86 out of 5 average rating, 14 reviews

Sapphire Beach Escape VIEWS! HGTV

Remodeled property in Sapphire Village recently featured on HGTV. Million $ views of the Caribbean! High end furnishings including a king bed and fully equipped kitchen. Onsite restaurant/bar featuring dining and poolside fare. Steps to beautiful Sapphire Beach. We supply beach chairs and beach equipment for your use! Great Snorkeling. Marina nearby. Walk down to Sapphire Beach for multiple restaurants, coffee spot, beach bar/grill, live music, rentals...

Superhost

Condo in East End

4.9 out of 5 average rating, 73 reviews

Beachfront Condo Retreat in St. Thomas

Welcome to Latitude Adjustment! - Stunning 2-bedroom, 2-bath condo with modern, elegant styling. - Just a 2-minute walk to beautiful Cowpet Beach. - Access to Elysian pool and hot tub with included wristbands. - Enjoy dining at nearby Caribbean Fish Market and Sangria's. - Amenities include AC, WiFi, washer/dryer, beach towels, and chairs. - Large covered porch for relaxation. - Complimentary concierge service to enhance your stay.

Top guest favorite

A panoramic view showcases a vibrant bay dotted with sailboats and motorboats. Lush greenery borders the shoreline, where sandy beaches meet turquoise waters. The sky features shades of blue and gray with fluffy clouds, providing a serene backdrop to the picturesque waterfront landscape.

Apartment in East End

5 out of 5 average rating, 38 reviews

Verena’s Holiday Haven -Great for Couples/Families

Discover Verena’s Holiday Home, a newly renovated retreat steps from Sapphire Beach and local restaurants. This charming property features a spacious master bedroom, two queen sofa beds, Smart TVs in every room, and a screened-in balcony perfect for relaxing in the ocean breeze. Ideal for families, couples, or groups, it’s your gateway to pristine beaches, vibrant dining, and unforgettable island adventures.

Superhost

A sandy beach is framed by tall palm trees, providing shade and a tropical ambiance. Gentle waves lap at the shore, with boats anchored in the serene turquoise water visible in the distance. Sun loungers are arranged on the sand, inviting relaxation.

Condo in East End

4.69 out of 5 average rating, 32 reviews

Gorgeous Condo East End Cowpet Bay St Thomas USVI

Nancy's St Thomas Vacation Rental units are located within the Elysian Beach Resort which sits on Cowpet Bay Beach on the highly desirable East End of St. Thomas, USVI, nestled between the Ritz Carlton and the St Thomas Yacht Club near the village of Red Hook. You’ll love my place because of the size, the openness, views, the location, the beach, the people. My place is good for families (with kids).

Superhost

Home in East End

4.9 out of 5 average rating, 58 reviews

TROPICAL TREEHOUSE IN PARADISE! ST. THOMAS, USVI

RELAX at the Tropical Treehouse in Paradise! One of the most unique art pieces on St. Thomas that you can sleep in! Minutes away from Redhooks ferrys or great restaurants & bars, Coki Beach, Coral World, Sapphire Beach, Sunset Harbor & Vessup beach. 20 minutes to Megans Bay! Recently renovated, hottub, bidet toilet seats, entire house has COLD Air conditioning!