172+ Vacation Rentals Near Pineapple Beach |
  1. U.S. Virgin Islands
  2. St. Thomas
  3. Pineapple Beach

Estia Villas - Vacation Rentals in Pineapple Beach

Wild Ginger Villa From US $704
         

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10.0 (1 Review)
Villa
Wild Ginger Villa
  • Air Conditioner
  • Parking
  • Pool

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Villa Palmera - 5-Star Modern Tropical Paradise From US $1,593
         

10.0 (158 Reviews)
Villa
Villa Palmera - 5-Star Modern Tropical Paradise
  • Air Conditioner
  • Parking
  • Pool

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Villa Marina Vista From US $470
         

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9.6 (50 Reviews)
Villa
Villa Marina Vista
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury Beachfront Duplex Villa on Sapphire Beach IV From US $497
         

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10.0 (2 Reviews)
Apartment
Luxury Beachfront Duplex Villa on Sapphire Beach IV
  • Air Conditioner
  • Parking
  • Pool

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Amazing villa steps from the pool with incredible views & FREE WiFi From US $408
         

9.6 (96 Reviews)
Villa
Amazing villa steps from the pool with incredible views & FREE WiFi
  • Air Conditioner
  • Parking
  • Pool

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Brand New Luxury Private Pool Villa Quartz - 5 mins walk to #Sapphire Beach From US $373
         

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10.0 (2 Reviews)
Apartment
Brand New Luxury Private Pool Villa Quartz - 5 mins walk to #Sapphire Beach
  • Air Conditioner
  • Parking
  • Pool

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10 MINUTE WALK TO BEACH, ON THE WATER! NEW HOT TUB! n GREAT VIEWS , NEW POOL! From US $877
         

9.6 (83 Reviews)
Villa
10 MINUTE WALK TO BEACH, ON THE WATER! NEW HOT TUB! n GREAT VIEWS , NEW POOL!
  • Air Conditioner
  • Parking
  • Pool

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Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club From US $2,569
         

9.4 (30 Reviews)
Villa
Everlasting MEMORIES (6) Master Suites Red Hook, East End ST Thomas, Yacht Club
  • Air Conditioner
  • Parking
  • Pool

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BEACHFRONT LUXURY at the Ritz! We own FOURTEEN residences, MOST DATES Available! From US $1,190
         

9.8 (86 Reviews)
Villa
BEACHFRONT LUXURY at the Ritz! We own FOURTEEN residences, MOST DATES Available!
  • Air Conditioner
  • Pool
  • TV

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HOORAY! YOU'VE FOUND THE GORGEOUS GETAWAY YOU'VE BEEN LOOKING FOR. From US $410
         

9.6 (55 Reviews)
Villa
HOORAY! YOU'VE FOUND THE GORGEOUS GETAWAY YOU'VE BEEN LOOKING FOR.
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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THE RITZ CARLTON Club in the USVI. No Passport needed. Feb/Mar 2026 in the Heat! From US $1,500
         

10.0 (7 Reviews)
Villa
THE RITZ CARLTON Club in the USVI. No Passport needed. Feb/Mar 2026 in the Heat!
  • Air Conditioner
  • Parking
  • Pool

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Gorgeous Oceanfront Villa From US $1,631
         

10.0 (1 Review)
Villa
Gorgeous Oceanfront Villa
  • Air Conditioner
  • Parking
  • Pool

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Ocean Front Villa Lush Property with Private Beach and Lagoon From US $1,772
         

10.0 (177 Reviews)
Villa
Ocean Front Villa Lush Property with Private Beach and Lagoon
  • Air Conditioner
  • Parking
  • Pool

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Private villa w/5 oceanfront suites, heated pool From US $1,705
         

10.0 (148 Reviews)
Villa
Private villa w/5 oceanfront suites, heated pool
  • Air Conditioner
  • Parking
  • Pool

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ONE BEACH ROAD; 6 Bedroom, 5 1/2 Bath Beachfront Oasis St Thomas VI From US $3,272
         

10.0 (122 Reviews)
Villa
ONE BEACH ROAD; 6 Bedroom, 5 1/2 Bath Beachfront Oasis St Thomas VI
  • Air Conditioner
  • Parking
  • Pool

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Villa Mirino - Fabulous Ocean Front East End Residence with Stunning Views. From US $936
         

10.0 (103 Reviews)
Villa
Villa Mirino - Fabulous Ocean Front East End Residence with Stunning Views.
  • Air Conditioner
  • Parking
  • Pool

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Good Vibes Only Waterfront Villa/Private Pool/Modern/Sun Decks/Majestic Views! From US $1,062
         

10.0 (90 Reviews)
Villa
Good Vibes Only Waterfront Villa/Private Pool/Modern/Sun Decks/Majestic Views!
  • Air Conditioner
  • Parking
  • Pool

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Brigadoon: A beautiful Villa In Red Hook/plus studio apartment sleeps 6 guests. From US $281
         

10.0 (89 Reviews)
Villa
Brigadoon: A beautiful Villa In Red Hook/plus studio apartment sleeps 6 guests.
  • Air Conditioner
  • Parking
  • TV

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A Large, Modern Villa With Infinity Pool, Spa & Expansive Outdoor Living Space. From US $1,013
         

10.0 (71 Reviews)
Villa
A Large, Modern Villa With Infinity Pool, Spa & Expansive Outdoor Living Space.
  • Air Conditioner
  • Parking
  • Pool

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'Sea La Vie' - Waterfront St Thomas Escape w/Pool From US $560
         

10.0 (62 Reviews)
Villa
'Sea La Vie' - Waterfront St Thomas Escape w/Pool
  • Air Conditioner
  • Parking
  • Pool

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Stop! You just found your vacation home w/breathtaking views! C'est Jolie D-27! From US $490
         

10.0 (57 Reviews)
Villa
Stop! You just found your vacation home w/breathtaking views! C'est Jolie D-27!
  • Air Conditioner
  • Parking
  • Pool

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4bd 4.5 baths House and two private apartments. Beautiful views! Self check in! From US $935
         

10.0 (41 Reviews)
Villa
4bd 4.5 baths House and two private apartments. Beautiful views! Self check in!
  • Air Conditioner
  • Parking
  • Pool

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Tropical Palm Villa- Ocean Views From All Rooms, Solar Power, Private Pool From US $879
         

10.0 (37 Reviews)
Villa
Tropical Palm Villa- Ocean Views From All Rooms, Solar Power, Private Pool
  • Air Conditioner
  • Parking
  • Pool

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Beautiful 3BR/4BA villa footsteps from beach From US $746
         

10.0 (36 Reviews)
Villa
Beautiful 3BR/4BA villa footsteps from beach
  • Air Conditioner
  • Parking
  • Pool

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★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Pineapple Beach.

Weather in Pineapple Beach

View the weather forecast for Pineapple Beach before booking your Pineapple Beach Vacation Rentals to confirm your best time to go.

December - February
High 84°F       Low 72°F
March - May
High 85°F       Low 72°F
June - August
High 88°F       Low 74°F
September - November
High 88°F       Low 73°F

Top Attractions Around Pineapple Beach, VI

Estiavillas offers a large selection of top attractions around Pineapple Beach. Research things to do on your vacation before you visit Pineapple Beach.


Sapphire Beach Trunk Bay Coki Beach Honeymoon Beach Virgin Islands National Park Bolongo Bay Magens Bay Beach Blackbeard's Castle Cinnamon Bay Beach Coral World Ocean Park Caneel Bay Beach Maho Beach St. John Spice Secret Harbour Beach Morningstar Beach St. Thomas Synagogue Lindbergh Bay Caribbean Genealogy Library Yacht Haven Grande Marina

Pineapple Beach Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Pineapple Beach?

There are a lot of options in Pineapple Beach. If you plan on staying in the Pineapple Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pineapple Beach:

How many vacation rentals are available in Pineapple Beach?

Currently, the total number of properties listed in 2026 is over 172 in the Pineapple Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Pineapple Beach.