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Places to stay near Pineapple Beach

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Top-rated vacation rentals near Pineapple Beach

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

The bedroom features a spacious bed with a light-colored blanket, complemented by wooden furniture, including a nightstand and wardrobe. Natural light enters through multiple windows, illuminating the room with a serene ambiance. A rustic decor adds charm, while a pet dog rests on the floor.

Cottage in Central

4.99 out of 5 average rating, 158 reviews

Caribbean Style Cottage

The 500sq. Tortuga Cottage is located in Fish Bay, St. John in the US Virgin Islands. The property is privately owned and adjacent to the National Park. This charming cottage places you within a 5 minute walk to Reef Bay beach and gives you access to many of St. John's greatest hiking trails. By car, we are 3 miles from town (Cruz Bay), where you will find all of your necessities. This is the ideal cottage for a couple or two friends. We have a full kitchen, a king Casper mattress, and much more

Top guest favorite

A sandy beach offers a serene view featuring clusters of leafy trees providing shade. The calm turquoise waters are visible in the background under a clear blue sky. Beach seating is scattered along the shoreline, inviting relaxation and enjoyment of the landscape.

Condo in East End

5 out of 5 average rating, 187 reviews

"H2Oh What a Beach!" condo: Walk-out Beach Access!

"H2Oh What a Beach!" condo Building A of Sapphire Beach Resort & Marina: ground floor unit with direct access to one of the most beautiful beaches in the Caribbean. Steps away from Sea Salt fine dining restaurant, Sapphire Beach Bar, Paradise Pie pizza, and Beach Buzz coffee shop. A mile from Red Hook featuring many restaurants & island ferries. Great beach, swimming, snorkeling, parasailing, and relaxing right outside your door. Be among the many visitors who LOVE this totally renovated condo.

A panoramic view reveals vibrant turquoise waters and several nearby islands, bordered by lush greenery. The sky is partially filled with fluffy clouds, and the distant shoreline features contrasting structures amidst the natural landscape.

Villa in St. Thomas

4.82 out of 5 average rating, 256 reviews

Amazing Villa in Paradise: Views of 9 Islands

Take advantage of our great rates at one of the 10 BEST places to stay on St Thomas. I personally promise you will love it! Incredible views over 9 islands from everywhere! 50 steps from the pool. This villa has all new furniture, gorgeous new kitchen, remodeled bath, high end sheets and towels, beach towels, beach chairs, snorkel gear, a 42" TV, free WiFi and so much more. I provide a robust info packet with all the best beaches, restaurants, bars, grocery store and more. You will LOVE it!

A tranquil view is presented from a covered deck, showcasing a vibrant panorama of Magen's Bay and the Atlantic Ocean, along with nearby islands. A hammock is suspended between wooden posts, inviting relaxation in the serene surroundings.

Apartment in St. Thomas

4.95 out of 5 average rating, 299 reviews

Casa Grand View

*NO CLEANING FEE* Located on the cool Northside of St. Thomas, our home looks out over a large flat-ish yard & a panoramic view of Magen's Bay, the Atlantic Ocean, and 20 small islands. Your unit has a private entrance 5 steps down from your dedicated parking space. Note: 1. There is no smoking allowed on the deck or in the apartment. 2. Unlike many Airbnbs we do NOT charge a cleaning fee so we ask our guests to sweep and wash their dishes before leaving. 3. No more than 4 guests at ANY time.

A serene beach scene features soft sand leading to clear turquoise waters. Smooth rocks delineate the shoreline, complemented by lush greenery in the background. A staircase ascends from the sand, providing access to the surrounding vibrant landscape and stunning coastal views.

Villa in Saint Thomas

4.93 out of 5 average rating, 133 reviews

Eau Claire- Magens Bay Affordable Beachfront Villa

Villa Eau Claire is a private gated affordable beachfront home directly on Magens Bay. Walk into the water at roughly half the price of any other waterfront home in the Virgin Islands. The property has 4 private individual villas each with breathtaking views of the bay. The Coral Studio is a 1 Bed/1 Bath villa located on a secluded beach in the world-famous Magens Bay. Guests will find the vibrant nightlife, charming boutiques, and fine dining restaurants just a few minutes away from home.

A vast ocean view is captured from a covered balcony, showcasing the stunning blue waters and nearby islands. Sailboats dot the tranquil sea, with a coastal community visible along the shoreline. Soft clouds drift across a clear sky, enhancing the serene coastal atmosphere.

Condo in Saint Thomas

4.93 out of 5 average rating, 147 reviews

★★★★★ Breathtaking Ocean Views-Private Balcony

★★★★★ REVIEWS ON MULTIPLE SITES. Luxurious Updated 1 BR/1 BA Condo w/WRAP AROUND BALCONY & BREATHTAKING views of St. John, BVIs, & CARIBBEAN SEA! Point Pleasant Amenities: 3 Amazing POOLS & INTIMATE BEACH. NEW FURNISHINGS 2019. Great LOCATION-Minutes to Fine RESTAURANTS & THE BEST BEACHES on St Thomas. 2 RESTAURANTS - Sun & Sea Bar & Grille right on the water & Ocean180. Fully equipped w/King Bed Queen Sleeper sofa Beach Chairs & Towels Cooler Outdoor Dining WiFi - 100MB OMG Views!

Top guest favorite

A modern living area features a large flat-screen TV mounted above a stylish wooden media console. A light-colored sofa and accent chairs are arranged around a circular coffee table, with large windows offering views of the ocean and islands beyond. Natural light fills the space.

Condo in East End

5 out of 5 average rating, 21 reviews

5 Star NEW Luxury Fully Remodeled 1x2 Pool & Beach

NEW! Spacious 1 Bedroom/2 Bathroom 1200 sq foot -2024 FULLY REMODELED OCEANFRONT Villa in St. Thomas, VI. This spacious villa has an all-new modern interior, spacious separate bedroom, 2 bathrooms, a private balcony and all the amenities! Situated on the sought-after East End, this luxurious retreat offers sweeping ocean/island views. Designed with modern elegance and spacious comfort in mind, the villa provides direct access to three pools, two gourmet restaurants, and a private beach.

A sandy beach is bordered by swaying palm trees, with rows of colorful lounge chairs set up for relaxation. Crystal-clear waters and gentle waves are visible in the background, while boats can be spotted in the distance under a bright, blue sky.

Condo in East End

5 out of 5 average rating, 11 reviews

*Margarita-ville Resort* Studio Suite! (Sleeps 2)

*Feel free to ask about discounts for your reservation!* Nestled in a cove fringed by waving palm trees, is a perfect tropical dream come true. So grab a beach chair, kick off your flip-flops, sip a tasty boat drink — and let your gaze rest upon an expanse of fine white sand, and crystal-clear waters. Restaurant on property, Coki Beach within walking distance, and very close to Red Hook for shopping and dining experiences! *PLEASE SEE GUEST ACCESS SECTION FOR USVI TAX INFO*

A panoramic view of turquoise waters meets lush green shores, dotted with distant islands. The landscape presents a serene coastal scene, with gentle waves lapping at the sandy beach, creating a tranquil atmosphere under a partly cloudy sky.

Home in East End

4.95 out of 5 average rating, 66 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.

A cozy living area features a comfortable sofa with a decorative pillow, alongside a sleek wooden coffee table. Large glass doors open to a private balcony with outdoor seating, showcasing views of the sparkling turquoise waters and surrounding landscape.

Condo in East End

4.89 out of 5 average rating, 284 reviews

Ocean View Sapphire Condo-Balcony & King Bed

Located at Sapphire Village-Amazing balcony and views of Sapphire Beach and its glimmering turquoise waters. Short walk to the beach and beach bar! 1 King bed, and one queen sleeper sofa. Property has hotel amenities including 2 pools, great snorkeling, 3 restaurants, beach bar, coffee shop & deli! Secure, safe location. Taxis are readily available nearby for rides to grocery stores, Red Hook for dinner, St. John Ferry, local beaches. 25 min from airport!

A sandy beach scene is depicted, featuring clear turquoise waters and a bright blue sky dotted with clouds. Palm trees and lush greenery frame the area, while groups of people enjoy the beach. Lounge chairs are visible on the sand, inviting relaxation.

Condo in St. Thomas

4.85 out of 5 average rating, 170 reviews

Breathtaking Views from Sapphire Village

Enjoy our studio unit located in Sapphire Village Condominium development! Our unit is smoke-free, pet-free, fully air conditioned, and offers breathtaking views of neighboring USVI and BVI. We are offering a vacation home with the comforts that we would want while we are vacationing on the island. The unit features a king bed, new sliding doors to the balcony as well as a new split air conditioning unit. New internet router January 2024

A colorful sign displays the name 'Margaritaville,' adorned with tropical elements including palm trees and a parrot. The sign is positioned above a thatched-roof structure, set against a blue sky and vibrant greenery, conveying a lively vacation atmosphere.

Apartment in St. Thomas

4.86 out of 5 average rating, 7 reviews

Margaritaville Resort Studio

Kick back and relax in this calm, stylish space. Margaritaville, nestled in a cove fringed by waving palm trees, is a perfect tropical dream-come-true. So grab a beach chair, kick off your flip-flops, sip a tasty beverage — and let your gaze rest upon an expanse of fine white sand, crystal-clear waters, and St. John island in the distance.

Popular amenities for vacation rentals near Pineapple Beach

Free parking on premises

Air conditioning

Condo rentals with wifi

A spacious living area features a vaulted wooden ceiling and large windows allowing natural light. Two light-colored sofas and a wooden coffee table are positioned on tiled flooring. In the background, a dining space is visible through sliding glass doors leading to an outdoor area.

Condo in St Thomas

4.82 out of 5 average rating, 157 reviews

SunnySide Villa! 2BR/3BA in Margaritaville resort

Top guest favorite

A marina scene is displayed, featuring a variety of sailboats and yachts moored alongside a serene blue waterway. Lush green palm trees frame the view, while distant islands are visible against a clear sky with a few fluffy white clouds.

Condo in East End

4.99 out of 5 average rating, 214 reviews

Stunning Ocean View w/Balcony~Shades of Sapphire~

Top guest favorite

A bright living area features large windows revealing ocean views. Natural light fills the space, which includes a sofa, dining table with blue placemats, and decorative plants. A wall-mounted flat-screen TV adds to the modern appeal. The color palette emphasizes calming tones.

Condo in Southside

4.95 out of 5 average rating, 108 reviews

Sea Dreams at Regatta Point Villas

A spacious living area features bright furnishings, including a white sofa and colorful armchairs. A coffee table with a decorative tray sits in the center, while a fully equipped kitchen is visible in the background. Floor-to-ceiling windows offer unobstructed views of the ocean.

Condo in Northside

4.99 out of 5 average rating, 143 reviews

VIEWS! Condo by Magen's Beach w/ POOL & generator!

A community pool is featured with clear, inviting water and a spacious deck. The area is surrounded by lush green hills, and distant vistas of the landscape can be seen under a partly cloudy sky. Lounge chairs are positioned along the pool's edge.

Condo in Saint Thomas

4.9 out of 5 average rating, 107 reviews

Little Fairway at Mahogany Run, Quiet & Cozy

An open-concept living area features high wooden ceilings and large sliding glass doors, providing unobstructed views of the ocean and surrounding islands. A dining table and chairs are visible alongside a turquoise cabinet, with a ceiling fan above for comfort.

Condo in Saint Thomas

4.93 out of 5 average rating, 105 reviews

C'est Jolie - Views! Views! Views!

Clear turquoise waters are framed by smooth, large boulders, with a view of boats floating nearby. Fluffy white clouds drift over a serene sky, while distant islands are visible on the horizon, enhancing the tranquil beach atmosphere.

Condo in Sapphire Beach

4.96 out of 5 average rating, 204 reviews

Salt Life at Sapphire Beach

The living area features a spacious sofa and a patterned armchair arranged around a coffee table. Large sliding glass doors provide a view of the ocean and access to the balcony. A dining table with chairs is positioned near the window, allowing for bright natural light.

Condo in St. Thomas

4.96 out of 5 average rating, 144 reviews

Oceanfront Condo Perfect Sunsets Backup Generator!

Family-friendly house rentals

The living area features a spacious gray sectional sofa and a light wooden coffee table, situated on a patterned rug. A flat-screen TV is mounted on the wall, complemented by decorative wall art and a lamp illuminating the space, creating a cozy and functional gathering spot.

Home in East End

4.81 out of 5 average rating, 36 reviews

Condo by the beach! Condo steps away from the beach!

A welcoming living area is furnished with a light-colored sofa and a glass-top coffee table. Natural light fills the space through sliding glass doors leading to an outdoor area. Neutral tones and simple decor create a relaxed ambiance, complemented by a woven rug underfoot.

Home in St Thomas

4.78 out of 5 average rating, 219 reviews

Beachside Condo

A seating area featuring two woven chairs with blue cushions is positioned near large windows. The view includes palm trees and vibrant ocean waters, framed by a turquoise wall and a decorative table with a small plant.

Home in Southside

4.77 out of 5 average rating, 60 reviews

Regatta Point! Ocean View Condo!

A tropical resort pool area is surrounded by palm trees, with a thatched-roof structure visible in the background. Colorful lounge chairs are positioned near the water's edge, while soft lighting creates a serene atmosphere as evening approaches.

Home in Charlotte Amalie

4.88 out of 5 average rating, 33 reviews

USVI Margaritaville* Private Studio Condo for 2*

A panoramic view captures lush green landscapes and calm waters under a blue sky adorned with fluffy white clouds. The distant horizon features gentle hills, while nearby rooftops offer a glimpse of the surrounding community and natural beauty.

Home in St Thomas

4.96 out of 5 average rating, 262 reviews

Amazing Ocean View with a spectacular location!

Top guest favorite

A clear view of the pool surrounded by lush greenery, with a spacious deck offering seating options. The ocean is visible in the background, featuring varying shades of blue. The semi-open cottage can be seen adjacent to the pool, blending harmoniously with the natural landscape.

Home in Saint Thomas

5 out of 5 average rating, 53 reviews

Caribbean Poolside Cottage

A spacious balcony offers panoramic views of lush green hills and sparkling blue waters. A small table and chairs are positioned for outdoor dining, surrounded by tropical plants and flowers. The combination of sunlight and clouds creates a serene atmosphere.

Home in East End

4.98 out of 5 average rating, 115 reviews

Brigadoon: RedHook Villa, (sleeps 6) WOW VIEW!

A sunlit deck features a private pool surrounded by a wooden railing, offering sweeping views of the ocean and lush hills. Palm trees sway gently in the breeze, completing the serene landscape under a clear blue sky dotted with fluffy white clouds.

Home in Saint Thomas

4.88 out of 5 average rating, 106 reviews

Villa Beso Del Sol - Three Bedroom Cozy Oasis

Apartment rentals with air conditioning

Top guest favorite

A scenic view is presented from a small deck, featuring lush greenery and colorful plants. Gentle hills are visible in the background, with the warm glow of a setting sun highlighting the landscape. The inviting outdoor space is enhanced by the surrounding nature.

Apartment in Northside

4.97 out of 5 average rating, 147 reviews

A Peace in Paradise!

An outdoor patio space is shown with wooden decking and a peaceful view of the surroundings. Two umbrellas provide shade, and patio furniture including chairs and a small table is arranged thoughtfully for relaxation. Lush greenery enhances the inviting atmosphere.

Apartment in St. Thomas

4.84 out of 5 average rating, 470 reviews

Hidden Hilltop Treasure

A well-appointed sleeping area features a spacious bed covered with a soft blue blanket, situated near two artwork pieces depicting serene landscapes. A bedside table holds a small plant, and a lamp provides gentle lighting, enhancing the room's tranquil feel.

Apartment in Saint Thomas

4.86 out of 5 average rating, 141 reviews

Traveler's Hideaway

A panoramic view of the coastline captures the vibrant blue waters meeting distant islands. Lush greenery and well-kept buildings with red rooftops are visible in the foreground, providing a serene backdrop to the expansive sky.

Apartment in Sapphire Beach

4.94 out of 5 average rating, 233 reviews

Captain and Mermaid Sapphire Condo

A small outdoor balcony features a round table set for two, accompanied by two light-colored chairs. The view includes lush greenery and the Caribbean Sea in the background, enhancing the relaxing atmosphere during twilight.

Apartment in East End

4.82 out of 5 average rating, 171 reviews

Two Ocean View II/Entire Apt/Walk to the Beach

A multi-level property is surrounded by lush greenery, featuring a spacious outdoor deck with sun loungers and umbrellas. The light-colored building has balconies with views and is accessible via a stone pathway, offering a sense of calm in a private environment.

Apartment in Charlotte Amalie

4.92 out of 5 average rating, 295 reviews

Beautiful view of Magen's Bay Beach

Top guest favorite

A cozy living area is equipped with a dark blue sofa, a stylish lamp, and a wooden TV stand. A vibrant rug is placed on the floor, and natural light filters through the white window curtains. A decorative plant adds a touch of greenery to the space.

Apartment in Saint Thomas

4.98 out of 5 average rating, 198 reviews

Hillside Hideaway

A sandy pathway leads to a tranquil beach, framed by lush green foliage on either side. Calm turquoise waters stretch towards the horizon under a partly cloudy sky, creating a serene coastal view.

Apartment in East End

4.9 out of 5 average rating, 114 reviews

Walk to Sapphire Beach

Other great vacation rentals near Pineapple Beach

A spacious bedroom is illuminated by natural light from large glass doors that open to captivating views. The comfortable bed is adorned with neatly arranged towels and a soft blanket. Tropical artwork is displayed on the walls, enhancing the serene atmosphere.

Condo in East End

4.88 out of 5 average rating, 8 reviews

Penthouse luxury with ocean views | Resort pools

A beach area is framed by palm trees and colorful seating. Lounge chairs in varying shades of green are positioned on the soft sand, while straw umbrellas provide shade. The tranquil water sparkles under a bright blue sky dotted with clouds, with distant hills visible along the shoreline.

Apartment in East End

5 out of 5 average rating, 11 reviews

Studio Dlx Condo @ Margarita-ville Beach Resort

A serene view of the ocean is captured, showcasing varying shades of blue and turquoise waters. Islands are visible in the distance, framed by lush greenery along the coastline. The clear sky enhances the tranquil atmosphere, inviting relaxation and exploration.

4.92 out of 5 average rating, 96 reviews

Down Island Dream - your perfect getaway! 1BR/1BA

A cozy bedroom is furnished with a king-sized bed dressed in crisp white linens. A ceiling fan circulates air, while a small refrigerator and television are positioned within view. Natural light filters through windows, illuminating the patterned area rug that adds warmth to the space.

Guest suite in East End

4.88 out of 5 average rating, 51 reviews

Guest Suite 100 steps from the Ocean solar powered

Top guest favorite

A sandy beach is lined with tall palm trees, casting gentle shadows on the ground. In the distance, a couple walks along the shoreline, with waves lapping at the sand. The turquoise water and clear blue sky create a serene coastal environment.

Condo in East End

5 out of 5 average rating, 10 reviews

On the Beach! 1 Min Walk to Dining - STJ Ferry

A serene beachfront scene features colorful chairs placed strategically on the sand, with gentle waves lapping nearby. The resort exterior showcases a welcoming entrance with water features and tropical landscaping. A cozy bedroom is highlighted by a spacious bed, complemented by neutral tones and natural light.

Condo in St. Thomas

5 out of 5 average rating, 10 reviews

Margarit@ville Beach Resort-1Bd Pres Ocean View

A sandy beach is bordered by clear blue waters and rocky formations. Gentle waves lap against the shore, creating a serene coastal ambiance. In the background, lush green hills and a few structures are visible, contributing to the peaceful tropical setting.

Condo in East End

5 out of 5 average rating, 13 reviews

Tropical Hideaway! Garden View @Point Pleasant

An outdoor pool area is surrounded by tropical palm trees, with lounge chairs arranged on the deck. A thatched-roof pavilion is visible in the background, along with vibrant umbrellas providing shade. The clear blue sky enhances the resort's tranquil ambiance.

Condo in East End

5 out of 5 average rating, 14 reviews

Island Paradise: Studio at Marg St Thomas

Destinations to explore