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Pineapple Beach, St. Thomas, U.S. Virgin Islands

Pineapple Beach vacation rentals

We found 137 vacation rentals — enter your dates for availability

Discover a selection of 137 vacation rentals near Pineapple Beach, St. Thomas that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $250 per night, and houses and condos are popular options for a stay near Pineapple Beach. Either way, you'll find a rental for everyone's needs.
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Find spaces that suit your style

Houses

View 46 Houses

Condos/Apartments

View 44 Condos/Apartments

Villas

View 31 Villas

Resorts

View 43 Resorts

Find the best place to stay — Pineapple Beach

Beautiful spacious apartment with a skyline view

2 Bedrooms · 1 Bathroom
$250 avg/night

St Thomas, USVI--2 Bedroom Villa

2 Bedrooms · 2 Bathrooms
$600 avg/night

QUIET ELEGENCE. 7 MINUTES TO RED HOOK ANDST. JOHN FERRY DOCK

Sleeps 4 · 2 Bedrooms · 1 Bathroom
$300 avg/night

Margarittaville near American Yacht Harbor

1 Bedroom · 1 Bathroom
$540 avg/night

Marriott Frenchman's Cove - Owner Direct

Sleeps 8 · 2 Bedrooms · 2 Bathrooms
$765 avg/night

Westin Bay Vista

2 Bedrooms · 2 Bathrooms
$1,290 avg/night

Search 137 vacation rentals

Top rated rentals — Pineapple Beach
Stayed Jan 2023

Great place to stay

Everything from check in to check out was properly handled. The place was outstanding from the white sand beach, to the food and all the smiling faces eagerly awaiting to help with any needs that might arise. This a perfect place for a week of rest a...

Todd L.
Todd L.

Circleville Ohio

Stayed Feb 2022

Great Stay

We just returned from our second wonderful stay at this property. The property was everything we needed. It was clean, well stocked and had a beautiful view. We enjoyed the pool and beach. The host was very easy to work with and very responsive, maki...

Cheryl C.
Cheryl C.
Stayed Feb 2021

Great place to relax

The property is immaculate and the rooms were very well appointed with higher end furniture, decor and comfortable beds. The bedrooms were spacious and there was plenty of room for 7 of us to gather in the living and dining areas without feeling cram...

Heidi H.
Heidi H.
Stayed Feb 2020

A Rare and Wonderful Experience

The Dancing Orchid Villa is beautiful, spacious and very peaceful. The view from the balcony is amazing. We particularly enjoyed being on the quiet side of the island away from the busyness of the commercial areas. Mary is a wonderful host and a grea...

Roger D.
Roger D.
Stayed Jun 2019

Needs Updating

First the good. Great location, did not have any trouble getting a taxi, on the beach, clean, comfortable furniture and the Property Manager, Amber was great. Now the not so good. This I not a one bedroom, it is a Studio or Efficiency. It does have ...

Theresa P.
Theresa P.
Stayed Apr 2018

Serene tranquil paradise on the hill

Couldn’t ask for anything better. The location was easy access to east central and west parts of island. Close to major beaches. Was able to enjoy the view of the island and ships docking fir the day. Entire property and unit kept clean and well main...

laurie f.
laurie f.
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How many vacation rentals are available around Pineapple Beach, St. Thomas?

Our 2023 property listings offer a large selection of 137 vacation rentals around Pineapple Beach. From 46 house rentals to 44 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses near Pineapple Beach?

Yes, of course. Vrbo has 46 Houses near Pineapple Beach. Our other popular types of vacation rentals near Pineapple Beach include:

  • Condos/Apartments: 44 rentals available
  • Villas: 31 rentals available
  • Resorts: 43 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Hotels and more.

Can I find a vacation rental with pool near Pineapple Beach?

Yes, you can select your preferred vacation rental with pool among our 72 vacation rentals with pool available near Pineapple Beach. Please use our search bar to access the selection of vacation rentals available.