Vacation rentals with a pool in Cowpet Bay

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Top-rated rentals with a pool in Cowpet Bay

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

Condo in East End

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

LocationFamilyOutdoor spaces

4.99 out of 5 average rating, 107 reviews

Top guest favorite

A scenic pathway leads from a stone staircase to a sandy beach, framed by swaying palm trees and lush greenery. The turquoise waters of Cowpet Bay are visible in the distance under a clear blue sky.

Condo in East End

Tropical Sands | Elysian Beach Resort | St. Thomas

Welcome to Tropical Sands, a luxurious beachfront condo at the Elysian Beach Resort, only 5 minutes from Red Hook! Perfect for family vacations and romantic getaways, this condo has it all! Enjoy stunning views from private balconies overlooking Cowpet Bay's turquoise waters. Amenities include kitchen, two full baths, WiFi, and washer/dryer. Guests enjoy all resort perks like pool, hot tub, water sports, and dining at Caribbean Fish Market and Sangria's Beachside Bistro. Truly a paradise escape!

LocationFamilyIndoor spaces

5.0 out of 5 average rating, 57 reviews

Top guest favorite

A modern condominium building stands prominently along Cowpet Bay, featuring a coral pink facade complemented by white roofing. Lush palm trees surround the area, while a small boat is anchored in the foreground. Calm waters reflect the bright blue sky, enhancing the serene tropical setting.

Condo in East End

Stay in the Pink Paradise at Elysian Beach Resort

This modern & bright 2 bed, 3 bath condo is located on beautiful Cowpet Bay just steps away from a quiet beach, pool with a hot tub, tennis court, & 2 on site restaurants. Large enough to bring your whole family, this 1500 sf condo includes 2 private bedrooms & a queen size sleeper sofa. Cowpet Bay is home to St. Thomas Yacht Club, Caribbean Fish Market, & Sangrias for your dining pleasure. Sit back, relax & enjoy views of Christmas Cove from the beach. Welcome to your stay in the Pink Paradise!

LocationValueAmenities

4.99 out of 5 average rating, 70 reviews

Guest favorite

Condo in East End

Stylish Elysian Condo | Beach, Pool & Restaurants

Perfect beach escape for 1-2 couples or small family! This spacious condo at the Elysian Beach Resort is just steps from beautiful Cowpet Bay on the East End of St. Thomas. Resort amenities (with no added fees), prime beachfront location next to the Ritz-Carlton. Bedroom features a comfortable king bed + queen-size Murphy bed that folds down easily for extra sleeping space in the living room. Fully equipped kitchen, this condo offers everything you need for a relaxing short or long-term stay

FamilyLocationLayout

4.93 out of 5 average rating, 112 reviews

Top guest favorite

A wooden bench with a sign reading 'SAIL AWAY' is positioned on a patio, overlooking the vibrant blue waters of a beach. Lush green foliage and palm trees frame the view, with rolling hills visible in the distance under a partly cloudy sky.

Condo in East End

Sail Away II-WOW Beachfront to Paradise Remodeled

Full property generator. 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. 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.

ValueLocationCheckout

4.95 out of 5 average rating, 144 reviews

Top guest favorite

A serene beach scene captures clear turquoise waters gently lapping against the shore. Lush greenery cliffs rise in the background, adding natural beauty to the landscape. A small boat and a few swimmers can be seen enjoying the calm sea, enhancing the tranquil atmosphere.

Home in East End

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.

LocationFamilyIndoor spaces

4.97 out of 5 average rating, 157 reviews

Superhost

An aerial view captures The Anchorage Condominiums along the shoreline, featuring lush green landscaping and the turquoise water below. A swimming pool and tennis courts are visible in the community area, while nearby palm trees sway gently in the breeze.

Condo in East End

Beachside 3BR Bedroom Condo/walk to 2 restaurants

Welcome to Luna Sol, a charming 3 bedroom condo in The Anchorage Condominiums. - Backup emergency generator - Steps from the beach and close to Red Hook - Shared gym and pool on premises - Beautiful shoreline walk to Cowpet Beach - 25-point property inspection for quality assurance - Complimentary concierge service for personalized trip planning - Large inventory of properties for larger groups - 24/7 maintenance and emergency hotline Have questions? Just ask!

FamilyValueParking

4.84 out of 5 average rating, 102 reviews

Top guest favorite

Lush greenery lines the shoreline, with vibrant red and orange flowers capturing attention. The clear turquoise water is visible, alongside a sandy beach in the distance. Features of the surrounding area include low-rise buildings and gentle waves lapping at the coast.

Apartment in East End

USVI St Thomas /Cowpet Bay East

Your family/friends will be close to everything when you stay at this centrally-located condo. Steps to the beach, beautifully kept landscaping, large pool and two great restaurants on site. The condo is the closest to the water and conveniently located by neighboring Ritz Carlton. Newly renovated and featuring high end king beds & linens. Snorkeling is right outside your veranda. Generator for continuous power. We have beach chairs, coolers and towels for the beach.

FamilyLocationCondition

5.0 out of 5 average rating, 28 reviews

Top guest favorite

A covered balcony showcases two rattan chairs and a small table, complemented by a potted plant. The view features vibrant blue waters, lush greenery, and distant hills under a clear sky, creating a relaxing outdoor space.

Apartment in East End

Gigi’s Luxury Beach Hideaway | Pool & Beach

Have fun with the whole family at our stunning and recently renovated 3-bedroom, 2-bathroom condo, located East End at the highly sought after gated property of Cowpet Bay West. This luxurious retreat comfortably accommodates up to 6 guests and offers breathtaking views, stylish furnishings, and resort amentities including a pool, hot tub, beach, watersport rentals, and two restaurants on property. Back-up generator on property for any island wide power outages.

FamilyLocationAccess

4.91 out of 5 average rating, 98 reviews

Top guest favorite

An aerial view of a contemporary home reveals a red roof and an infinity pool lined with lounge chairs. Surrounding greenery enhances the sense of privacy, while a spacious driveway provides easy access. Large windows allow for plenty of natural light to enter the interior.

Villa in Charlotte Amalie

Hilltop Paradise Vacation Package with Jeep

Start your next adventure and step into this brand new contemporary modern home hidden in the hills of St. Thomas. Here, you will be greeted with incredible, breathtaking views and an infinity pool overlooking the beautiful Charlotte Amalie. This carefully designed retreat sets the tone for a perfect adventure getaway for a group of friends/couples, or the perfect relaxation stop for a family. Whatever you choose, this home will not disappoint.

FamilyLocationSleep quality

4.99 out of 5 average rating, 104 reviews

Guest favorite

Condo in East End

Ocean Front Steps to beach w/ pool and restaurant

Stay at Océan Bleu, a 2-bedroom, 2-bath oceanfront condo in Cowpet Bay, St. Thomas. Enjoy stunning views, a private balcony, steps to beach, pool, hot tub and two restaurants. The condo has modern appliances, beach decor, and a fully equipped kitchen. Fast Starlink WiFi, linens, beach towels included. Located near Red Hook and the Ritz, with private parking and a gated community for peace and security. No smoking on the balcony or inside.

ValueLocationNearby

4.98 out of 5 average rating, 124 reviews

Top guest favorite

A serene beach setting is captured, featuring gentle waves lapping at the shore. Sun loungers are positioned in the foreground, surrounded by palm trees. Calm waters reflect the soft hues of a sunset, and boats can be seen anchored in the distance.

Condo in East End

Amazing Beachfront Condo with Pool & Restaurants!

Elysian Beach Resort offers a stunning condominium with a private entrance, full kitchen, two king bedrooms, and one twin bed, one full size pull-out sofa along with three bathrooms. Each room boasts breathtaking views of the Caribbean ocean, and guests have full access to the beach, pool, hot tub, and tennis courts. On-site dining options include the Caribbean Fish Market, Sangria's, and the Pool Bar.

ValueFamilyBathroom

5.0 out of 5 average rating, 77 reviews