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Pineapple Hideaway | Oleander Gardens

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Beach nearby, sun-loungers, beach towels - Pineapple Hideaway | Oleander Gardens (Gregory Town)
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Nestled in the tropical oasis of Oleander Gardens, this Caribbean Front Home offers a serene retreat with direct access to the sea and panoramic views from nearly every room. Unwind on your private cliffside haven, go snorkeling or diving in the lively coral reef just steps away, and enjoy top-notch bedding and amenities like a well-equipped kitchen.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 9

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Add dates for prices

About this property

Pineapple Hideaway | Oleander Gardens

  • Located in the lush tropical community of Oleander Gardens you will find this completely remodeled home. Oleander Gardens is a community on the ‘Caribbean’ side of the island and features a picture-perfect beach nestled in a cove. Oleander Gardens is nestled between the award winning ’The Cove’ resort, Gaulding Cay and neighbors too some of the worlds biggest rock stars! The home is perched perfectly on one of the islands most beautiful Bluffs (cliffs) with direct, private, access to the ‘Caribbean Sea.’ This island home is the only solar property within the community, providing clean and reliable energy with the grid as back up. Completely pampered inside and out, no detail was overlooked when remodeling the property in Summer of 2022. Featuring top quality bedding, fixtures and amenities, you will find comfort no matter how long you stay.

    This Island Caribbean Front Home is located in the tropical oasis of Oleander Gardens. A three minute walk to the community beach.

    Exclusive, private water access directly in the backyard leads you right into the lively coral's ideal for snorkeling, spear fishing and diving.

    For the thrill seekers we have two Cliff Jumping locations in the backyard that will get your adrenaline pumping!

    The sea turtle accents found throughout the home is a tribute to the family of Sea Turtles that live in the back yard. More than one time a day you'll be able to see their majestic beauty...

    The property has just been pampered (2022) with a total makeover!

    We ARE pet friendly! We provide dog bowls, and a dog bed. Please make sure your furry friends remain off the beds.

    ** Panoramic Caribbean views can be found from nearly all rooms!

    All bedding is top quality, featuring UGG Egyptian cotton sheets, Tommy Bahamas quilts, feather down pillows and Serta mattresses or NECTAR mattresses.

    The kitchen is well equipped to fix up a quick meal or a savory Sunday feast!

    Stackable Washer and Dryer is available for use

    Brand new Air Conditioners have been installed throughout the home to deliver ultimate comfort while on island time

    Housekeeping does a meticulous job following strict COVID 19 protocol before and after each stay. For stays longer than 5 days we do offer a continued cleaning service, if so desired.

    Gaulding Key, Glass Window Bridge, Queens Bath and the Island Blow Hole is only a 5 minute car ride!

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car available
  • Wheelchair-accessible parking and van parking available

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Toaster

Bedrooms

  • 3 bedrooms
  • Egyptian cotton sheets

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Patio
  • Yard

Laundry

  • Laundry facilities
  • Washer/dryer

Work spaces

  • Printer

Comfort

  • Air conditioning

Pets

  • Pet friendly
  • Welcoming dogs only
  • 3 pets total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 4 accessible parking spaces
  • In-room accessibility
  • No lift (single-level property)
  • Wheelchair-accessible parking
  • Wheelchair-accessible van parking
  • Designated smoking areas

Services and conveniences

  • Housekeeping on request

Location highlights

  • Near the ocean
  • On the waterfront

Things to do

  • Gym
  • Water sports equipment
  • Ecotours nearby
  • Fishing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • No smoke detector (host has indicated there is no smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden
  • Housekeeping (on request)
  • Solar energy

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Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in and check-out are available

Check-out

Check-out before 10:00 AM
Contactless check-out

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Welcoming dogs only
3 total pets
Restrictions apply; for more information contact the property on the number on the booking confirmation

Children and extra beds

Children are welcome

Events

Events allowed: family gatherings, birthday parties, weddings

Smoking

Smoking allowed: in designated areas

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 40
This property uses some solar energy
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is no smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the area

Located in Gregory Town, this holiday home is on the waterfront. Dr. Albert Johnson Memorial and Glen Stewart Mansion are local landmarks, and some of the area's activities can be experienced at James Cistern Dock and Government Dock. Discover the area's water adventures with scuba diving, snorkelling and fishing nearby, or enjoy the great outdoors with ecotours. Visit our Gregory Town travel guide
View more Holiday homes in Gregory Town
Map
Gregory Town, Eleuthera

What's nearby

  • Glass Window Bridge
    Glass Window Bridge
    7 min drive - 5.1 km
  • Queens Bath
    6 min drive - 4.2 km
  • Gaulding Cay Beach
    7 min drive - 4.2 km
  • Hatchet Bay Cave
    13 min drive - 8.8 km
  • Whale Point
    14 min drive - 8.9 km

Getting around

  • North Eleuthera (ELH-North Eleuthera Intl.)
    23 min drive

Restaurants

  • Daddy Joe's
    5 min drive
  • Lutra Vibes Bar & Grill
    5 min drive
  • Unca Jenes
    5 min drive
  • Glass Window Bar & Grill
    9 min drive
  • Sunset Bar @ The Cove
    18 min walk

Frequently asked questions

Is Pineapple Hideaway | Oleander Gardens pet-friendly?

Yes, this property allows dogs (limit 3 total). Some restrictions may apply, so please contact the property for more details.

How much is parking at Pineapple Hideaway | Oleander Gardens?

On-site parking is available at the property.

What time is check-in at Pineapple Hideaway | Oleander Gardens?

Check-in begins at 3:00 PM.

What time is check-out at Pineapple Hideaway | Oleander Gardens?

Checkout is at 10:00 AM.

Where is Pineapple Hideaway | Oleander Gardens located?

Situated on the waterfront, this holiday home is 2.4 mi (3.9 km) from Gaulding Cay Beach and 2.6 mi (4.2 km) from Queens Bath. Glass Window Bridge and Surfers Beach are also within 6 miles (10 km).

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Pineapple Hideaway | Oleander Gardens Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 20 out of 20 reviews
Rating 8 - Good. 0 out of 20 reviews
Rating 6 - Okay. 0 out of 20 reviews
Rating 4 - Poor. 0 out of 20 reviews
Rating 2 - Terrible. 0 out of 20 reviews

10

Cleanliness

10

Location

Reviews

Verified

10/10 Excellent

Greg D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Easy communication and check-in. Beautiful home with an incredible view!
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

David C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We really enjoyed our time at Pineapple Hideaway. It was a perfect place to spend Christmas with our children and grandchildren. Thanks for the special Christmas touches and for the baby tub. We especially enjoyed our time (dinners) on the porch and snorkeling out front at the ocean access.
Stayed 19 nights in Dec 2025
Verified

10/10 Excellent

Paul T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Outstanding property. Very clean, comfortable beds, snorkeling was excellent!
Stayed 5 nights in Jul 2025
Verified

10/10 Excellent

Janelle R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property with all the things needed for several people and lots of meals served in the house! Our second time here and hopefully not our last! Cody was so super helpful with any requests - you won't have many requests because it's all there! We had a wonderful time.
Stayed 4 nights in Nov 2025
Verified

10/10 Excellent

Lisa L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing Stay

My husband and I had a great 5-night stay at Pineapple Hideaway! Clay's communication was outstanding and so helpful. The outdoor area is magical and the house is just as pictured!
Stayed 4 nights in Nov 2023
Verified

10/10 Excellent

Loralyn L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A beautiful stay!

This house is gorgeous and so fun! The house was so clean, the owners were so responsive through our stay. The water is the most gorgeous water I have ever seen. Thank you!
Stayed 2 nights in Feb 2024
Verified

10/10 Excellent

Cohleen C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wow! Wow! Wow!

Such a wonderful home. Every amenity you can think of, including alexa. I loved the screened in porch- we basically lived in there. Great location. Would definitely stay here again.
Stayed 2 nights in Dec 2023
Verified

10/10 Excellent

Martin K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely house on top of a rock

we - a family of 6 - enjoyed our stay at this place. great communication with cody, easy going, early check-in possible, fishing gear and a lot of things to play and to do. well equipped, lot of stuff there. sea was a bit rough, bit caught some fish from the cliff. thanks cody!
Stayed 2 nights in Oct 2024
Verified

10/10 Excellent

Josephine H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pineapple Hideaway is a true hidden gem

We loved this place. Lots of room, thoughtfully appointed, plenty of fun games, amazingingly stocked kitchen which was great as my husband loves to cook. Extremely thoughtful hosts available if needed and text sickens to be sure we had everything we needed. We visited with another couple and The extra bedroom in separate building allowed for extra privacy. the set up along the water with hammock, table and steps into the water was Fantastic. We enjoyed morning coffee by the water and amazing sunsets in the backyard. Even enjoyed afire in their fire pit. What a grand time and a perfect place in Eleuthera. Perfectly located on the island for a variety of beach visits
Stayed 7 nights in Feb 2025
Verified

10/10 Excellent

Asst. Chief Jake T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely perfect homebase for exploring the island

We could not have asked for a better location for our stay on Eleuthera! Cody was fantastic to work with and maintained excellent communication throughout our stay. The home was perfect for 7 of us to sleep comfortably. My wife and I loved outdoor shower and listening to the sound of the ocean every night from the adjoining structure. We were able to make family style dinners every night, in the well laid out kitchen where we cooked the fish and lobster the kids speared throughout the day. The backyard was what sealed the deal with this home! the snorkeling was spectacular and everyone loved jumping from the cliffs into the Caribbean! We would not hesitate to stay here again!
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Nona M. S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cody worked with us on an early luggage drop. So kind! And the house is comfy with an amazing view!
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

marcelo d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property with an outstanding host

Gorgeous property. I would stay there again in a heart beat
Stayed 1 night in Nov 2023
Verified

10/10 Excellent

Mariah W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Hidden Gem in North Eleuthera!

The house + host were absolutely amazing. We couldn't have asked for anything more- highly recommend staying here!
Stayed 4 nights in Mar 2023
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pineapple Hideaway

I absolutely love this place and the entire island! It was a different experience where there was basically zero commercialization and everything was locally run by the islanders. We snorkeled out front every day and there are beautiful public beaches less than a mile away. Everyone was super nice and we've already booked for next year. If you want to experience freedom then this place is for you. Pineapple Hideaway is located in a great location and the view is incredible all day long and the snorkeling is honestly some of the best on the island. The only time i've seen so many stars at night was in Montana....its wonderful.
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

Brett C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Eleuthera!

I can’t say enough good about this place! It is exactly as described in the listing and so much more! A quiet neighborhood, palm trees, an amazing set of steps down to the water, a great little beach with a perfect snorkeling spot, a well appointed kitchen, comfortable mattresses, a beautiful shower, the list goes on and on! Cody is an excellent host and is very responsive. The house and location could not be more perfect both as a beautiful location, and as a starting point for all of the beaches and adventures Eleuthera has to offer. Whether it’s Harbor Town, sea turtles, cliff-top ocean blow holes, snorkeling, restaurants or whatever your adventure may be, this is the place to launch from. We’ll be back!
Stayed 4 nights in Jul 2023
Verified

10/10 Excellent

Cara G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pineapple Hideaway - perfect location to unplug and recharge

It was our first visit to Eleuthera and we had the BEST time exploring the island. The people of the island are WONDERFUL! We were traveling with our 3 and 6 year old daughters and the home was perfect for us. We loved the neighborhood and the little beach just up the street. All the neighbors were so nice and helpful too. I would definitely recommend this location! The view and walkway to the water are amazing - although we had to keep a close eye on our girls because it could be dangerous. The home was just what we needed. The beds were comfy and the AC worked well. We used the screen porch a lot and it was also nice to have a yard. The oven did not work for our vacation and that was a bummer because we couldn't cook some things we had planned. We also lost power and thought the home was on solar and wouldn't lose complete power, but it did. Cody was responsive throughout the process. We would stay here again for sure! Thank you for the wonderful vacation!
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

Alex G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gem of a place

Pineapple Hideaway is a true gem. It is situated on a small cliff overlooking the Caribbean ocean in a small and quiet development less than 30 minutes from North Eleuthera airport. We rented a car through Thurmon at Sabal Palm Car rental who I highly recommend! The views and sunsets from Pineapple Hideaway are spectacular. On a calm day the sea is like an aquarium. The reefs, corals and marine life all visible right from the cliffs. There are stairs hewn into the cliffs taking you down to a landing by the ocean with a picnic table and a hammock. I had coffee here every morning! More steps give you direct access into the ocean for swimming and snorkeling - which was amazing. The amount of sealife you can see in or out of the ocean is incredible. We spotted turtles, a nurse shark, lion fish feeding on the corals, puffer fish, barccuda and countless more colorful tropical fish. There is a trunk full of snorkeling gear available for you to use. The back yard overlooking the Caribbean is large enough to throw a football or frisby or just hang out with the family and picnic. The house itself is fantastic with a very modern touch. It has clearly recently been redocorated and everything has a new feel. Everything you need is available. A big plus is the reverse osmosis water filter that provides you with potable water at the kitchen sink. There are a ton of games available. There is even an "Alexa" hooked up for turning on kitchen lights and bantering with. The king sized bed in the master bedroom was amazingly comfortable. The shower is absolutely massive. Our favorite part of the house though was the screened in porch area with comfortable couches which allowed us to remain "outside" even when we were indoors. There are several dining options nearby. We ate at Daddy Joes just down the road which was delicious and had live music. There is a fancy hotel on the adjacent propery called The Cove, but when we called to make a reservation at their restaurant they were full. My favorite place, though, was Unka Genes. This restaurant/bar has a real local vibe and the food is delicious. I highly recommend the Gully Wash. Cody, the owner, was easy to reach and responsive. He has thought of every way to make this a special place to vacation.
Stayed 4 nights in Dec 2022