Vacation rentals with a pool in Charlotte Amalie

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Charlotte Amalie

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

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Guest favorite

Home in NorthSide

5 out of 5 average rating, 28 reviews

Heated Pool, OceanView, Generator, Local Discounts

Welcome to Sunrise Villas by Stacie! Enjoy island living at our newly constructed home offering breathtaking ocean/island views. Enjoy the heated pool with baja sun deck, bubblers/jets/lights. Relax in our spacious indoor/outdoor space with 20 foot sliding door, huge kitchen, bar, and fireplaces. No worries about island power with our whole home generator. Perfect escape for families with older children, couples, or a group of friends - book with our home right next door for up to 6 more guests!

Guest favorite

Villa in East End

4.97 out of 5 average rating, 36 reviews

Private Pool Getaway in Smith Bay (Beach Nextdoor)

Elegant quarters in established community with private sparkling pool, washer/dryer, dishwasher, WiFi, reliable AC, and generator for islandwide power outages. Explore famous Sapphire Beach Nextdoor 5min walk. You enjoy a calm, cozy villa equipped for couples, family, or solo travelers. Savor delights at Pangea's restaurant onsite or practice yoga on the private patio. Take a short taxi ride to St. John ferry terminal or Redhook nightlife. Book here for 6 guests to feel comfortable in Rock City!

Guest favorite

Rental unit in East End

4.98 out of 5 average rating, 41 reviews

Private Pool • Beach Access • BBQ • King • Gen.

Welcome to your 5.0-rated "Poolside Paradise"! Enjoy your own private pool steps from your bed & a 5 minute walk to restaurants & nightlife at the beautiful & lively Sapphire Beach! ★ "What a gem!! Very private, clean, and well-stocked. Heidi was super sweet and helpful. We absolutely loved our stay and will be back." ☞ Newly Renovated ☞ Onsite Generator ☞ King Bed ☞ Fast Wifi ☞ Washer & Dryer Nearby ☞ 3 mins to Red Hook (Taxi stand near by) ☞ Parking Available ☞ Secure Double-Gated Entrance

Guest favorite

Villa in East End

4.81 out of 5 average rating, 225 reviews

Private Pool Romantic Villa. Walk 2 Sapphire Beach

I fell in love w/ life on the island of perpetual summer. There's something special about having your own villa w/ a private pool. I also love the garden shower & the location. Pangea, the restaurant on site is phenomenal. The property is so close to my fave spots. Beautiful Sapphire Beach is in walking distance via a gate at the south end of the property. It boasts the Beach Buzz coffee & bfast spot, a Beach bar & grill w/ live music weekly, Paradise Pie pizza & SeaSalt fine dining restaurants.

Guest favorite

Home in Southside

4.95 out of 5 average rating, 100 reviews

Sunset Terrace – Perfect home for your vacation!

Sunset Terrace Villa offers a private and accommodating home for your Caribbean vacation! This fully air-conditioned home offers a private pool, new renovations, furnishing and spectacular views of the water and surrounding islands. Beautiful sunsets are an everyday experience and can be enjoyed inside or from the covered, outdoor patio space. Centrally-located in a safe and scenic neighborhood. Nearest beach is only a 5 minute drive. Concierge service included. Designed by Ashley-Interiors

Guest favorite

Condo in East End

4.9 out of 5 average rating, 200 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!

Guest favorite

Rental unit in St. John

4.94 out of 5 average rating, 68 reviews

Private Pool luxury 1 bedroom Ocean view - 5 minut

Cruz Bay Luxury 1-bedroom with private pool located in quiet safe residential community. Very spacious and post hurricane renovation complete. Chef's kitchen, Wolf 6 burner gas stove, granite countertops, stainless steel appliances, vaulted ceilings, large deck, pool, 2 private outdoor shower, sunset views to St. Thomas. The most beautiful rental for 2 adults available (can accommodate more with sleeper sofa). Close to town, parking onsite included. We can arrange private dinners, in villa sun

Superhost

Villa in Cruz Bay

4.88 out of 5 average rating, 16 reviews

Sunset View Pool Villa Close to All of St John

AMAZING Pool Villa with lots of privacy and 4 equal master bedrooms. Villa Colorado – one of the most popular luxury St John vacation rental villas. The home offers four equal king bedroom suites, with spectacular ocean views from every room, brilliant Caribbean sunsets, and a 32′ pool. The combination of equal king bedroom suites and a large pool makes us unique among St John’s rental villas. With lots of space, Villa Colorado is great for families, big groups, weddings and special events.

Guest favorite

Rental unit in Saint Thomas

4.98 out of 5 average rating, 164 reviews

Hillside Hideaway

Perfect getaway for island romance, 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.

Guest favorite

Rental unit in East End

4.94 out of 5 average rating, 16 reviews

Generator & Private Pool Sapphire Beach 5m walk 8

★★★ Beach & Pool ★★★ quick 5 minute walk to Sapphire Beach! You'll have a great time at this modern comfortable place with private pool. Perfect for couples and close family to relax & rejuvenate in totally private pool setting. Free parking, WiFi, 55" cableTV, modern large living room, full stainless steel kitchen. Close to everything. Popular restaurant/bar on premises. We offer Travel Insurance to protect from unexpected health, coronavirus and travel related issues (100% refund)

Guest favorite

Condo in East End

4.98 out of 5 average rating, 170 reviews

Sombrero Sapphire Village Studio

Newly renovated studio on the top floor of the Saba building with spectacular unobstructed views. Pool, restaurant, parking and laundry facilities on property. Short walk to the marina and to beautiful Sapphire Beach and five minutes away from Red Hook for shopping, restaurants and the ferry to St. John. Condo office with laundry and movie and book library. Secure gated entrance.

Guest favorite

Villa in East End

4.89 out of 5 average rating, 307 reviews

Romantic Villa with Private Pool - Rave Reviews!

A uniquely romantic tropical getaway - with our own generator! - for you and your special someone or a serene escape for rejuvenating solitude. Enjoy a memorable vacation with your own private and secluded pool available 24/7 and a restaurant just steps from your door. Easy 5-minute walk to Sapphire Beach.