PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest | Cottage in Key West

10.0 (222 Reviews) |   2 Bedrooms  2 Bathrooms  4 Guests  Stay&Play
Downtown Cottage | PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest

2 Bedroom Cottage in Downtown, Key West

WELCOME TO PINEAPPLE COTTAGE!
The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town Key West. It offers a private pool and is just half a block away from Duval Street, making it an ideal tropical oasis for your vacation.
As you enter the cottage, you'll step onto a deck overlooking the backyard, where you'll find the inviting private pool, a charcoal grill, and various seating and lounging areas surrounded by lush tropical landscaping, ensuring your privacy and creating a serene atmosphere.
Inside, the cottage features an open living area and kitchen space, perfect for easy flow and entertaining. The living area is equipped with a fully loaded entertainment system, including cable TV, a sound system, CD player, and DVD player. You'll also find board games for some indoor fun, whether in the living room or at the outdoor table. The kitchen is fully equipped and includes a breakfast bar with bar chairs, providing a convenient division from the couch and comfortable viewing chairs in the living room.
On the first level of the cottage, there is a full bathroom and a hidden bedroom tucked away to the right of the kitchen. This bedroom features a queen-size bed and all the amenities necessary to ensure a comfortable stay. You can choose to keep the curtains and blinds closed for a peaceful sleep-in or open them up to let the tropical sun awaken you for an adventurous day.
The second floor of the cottage offers another spacious living area with cable TV, a large comfortable sofa, and chairs for relaxation. The master bedroom on this level boasts a king-size bed and an en-suite full bathroom. Additionally, the washer and dryer are conveniently located in this bathroom for the guests' use.
The backyard of the Pineapple Cottage is a true haven. With its sparkling pool, grill, and dining areas, you have everything you need to enjoy meals at home while entertaining and making the most of your vacation. The cottage location in the Old Town district allows you to easily walk to Duval Street, where you'll find a variety of shopping, beaches, and restaurants in close proximity.
Overall, Pineapple Cottage offers top-of-the-line amenities and comfort, ensuring a delightful and enjoyable stay in Key West.
Important Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know.
**Pool heat is optional at $25 a day.**

PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest is located in Downtown. PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest provides accommodation, featuring Parking, TV, Barbecue/Outdoor Cooking, among other amenities. This Cottage features Parking, TV, Barbecue/Outdoor Cooking, to make your stay a comfortable one.

PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest has 2 Bedrooms , 2 Bathrooms, and max occupancy of 4 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Cottage because of the excellent services rendered by the owner or manager of this Cottage, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cottage has a friendly neighborhood, and the Downtown has interesting places to visit. If you want to learn more about the Cottage in Downtown, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pool
  • TV
  • View
  • Private Pool
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Guest Services
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Check-in Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy Pets not allowed
Other Policy 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 host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip parties and events are allowed on site safety features at this property include a fire extinguisher and a first aid kit special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
 
Key West, 33040, USA

What Our Guests say 500 + Reviews

Jun 13, 2025 11:59:25 PM
Summary: The location was amazing. We could walk to all kinds of things but it still felt like you were in your own private oasis in the pool/yard. Couldn’t have asked for a better spot.
Jun 11, 2025 11:53:00 AM
Summary: Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Pineapple Cottage was perfection! The private pool and back patio were amazing, beds were comfortable, home was cute and clean. Preferred Properties was excellent, they really went out of their way to make sure we were comfortable and we wanted for nothing. 10/10, we'll be back!
Kirsten M. Kirsten M.
May 25, 2025 12:25:14 AM
Summary: stayed for 4 nights. Absolutely love this house and location. The house was cute, well maintained and tactfully decorated. The best part was 1-2 blocks from all the activity but very quiet at the property. Kind of hidden. The outdoor pool was so great. loved floating around everyday after exploring the town. communications were quick and efficient. had a great experience and would highly recommend.
Kimberly s. Kimberly s.
Apr 30, 2025 11:59:57 PM
Summary: Excellent.
John S. John S.
Apr 20, 2025 01:21:20 AM
Summary: This house is everything it says it is. There were no surprises and no disappointments. It's a beautiful property in the heart of downtown Key West. We took an Uber from the airport and never once wished we had a car. We walked to everything. We will be back next year.
Sherri G. Sherri G.
Feb 25, 2025 12:19:00 PM
Summary: Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The location of Pineapple Cottage couldn't be better, close to all the action but you'd never know it. The pool was wonderful. We chose to have it heated and it was prefect for floating after getting in from the beach. The cottage itself was exactly as described. Angela from Preferred Properties was the there to answer all of our questions from check-in to check out. We will be returning!
Beverly C. Beverly C.
Jan 20, 2025 08:35:14 AM
Summary: Exceeded all expectations. Even the bathroom tissue was top notch.
Daniel C. Daniel C.
Jan 13, 2025 10:23:46 PM
Summary: Wonderful and clean house
nick c. nick c.
Dec 24, 2024 09:52:00 PM
Summary: Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Excellent in every way! No complaints whatsoever.
eberts j. eberts j.
Dec 16, 2024 04:16:00 PM
Summary: Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything went perfect from the rental agency support and communication, house cleanliness and comfort, pool and location. We are already booked for next year!
Kevin F. Kevin F.

FAQ's

Is this Downtown cottage pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Downtown cottage have a swimming pool?

Yes, this Downtown cottage has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Downtown cottage?

Best-rates for the Downtown cottage starts from $1,267 per night with includes Wellness Facilities, View, Sports/Activities, Entertainment, Laundry, Ocean View, Guest Services, Pool, Private Pool, Balcony/Terrace, Oceanfront, Security/Safety, Bedding/Linens, Child Friendly, Internet, Air Conditioner, Parking, TV, Barbecue/Outdoor Cooking, Kitchen StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Downtown cottage a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this cottage Good or guests have recommended them suitable for families. As reported by the owner or manager, the cottage has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Downtown cottage wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Downtown cottage has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Downtown cottage?

Based on the information reported by the owner or manager, the Downtown cottage indicates 1 day stay policy at this cottage. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Downtown cottage?

Based on the information reported by the owner or manager, details for the cancellation policy for the Downtown cottage are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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