Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath | Cottage in Key West

10.0 (237 Reviews) |   2 Bedrooms  2 Bathrooms  4 Guests
Downtown Cottage | Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath

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.
Guests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.
**Pool heat is optional at $25 a day.**
Virtual Tour Url: https://my.matterport.com/show/?m=khS5nBShNSP

Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/25Bath is located in Downtown. Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/25Bath provides accommodation, featuring Pool, TV, Sports/Activities, among other amenities. This Cottage features Pool, TV, Sports/Activities, to make your stay a comfortable one.

Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/25Bath 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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Amenities

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

Facility Overview

Air Conditioner
  • Heating
  • Air conditioning
Bathrooms
  • Hair dryer
  • Shower
  • Towels provided
  • 2 bathrooms
Bedroom
  • 2 bedrooms
  • Bed sheets provided
  • Living room
Kitchen
  • Refrigerator
  • Microwave
  • Coffee/tea maker
  • Stovetop
  • Toaster
  • Oven
  • Cookware/dishes/utensils
  • Spices
  • Dishwasher
Laundry
  • Laundry facilities
  • Washing machine and dryer
Parking
  • Onsite parking
Pet Friendly
  • No pets allowed
Accessibility
  • Smoke-free property
Activities
  • Kayak on site
  • Golfing on site
  • Marina nearby
Entertainment
  • Games
  • Stereo
  • DVD player
  • Smart TV with cable/satellite service
General
  • English
Guest Services
  • Iron/ironing board
  • Concierge services
  • Housekeeping (on request)
Internet
  • Free WiFi, with speed of 25+ Mbps
Outdoors
  • Patio
  • Fenced yard
  • Charcoal grill
Security/Safety
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Fire extinguisher
Spa
  • Private pool
  • Heated pool
  • Shared/communal pool

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.
Event Policy
No events allowed
Pet Policy
Pets not allowed
Smoking Policy
Smoking is not permitted

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 onsite parties or group events are strictly prohibited 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

Reviews

Gigi A.
Jan 27, 2026 08:58:23 PM
Review Score:   10
Summary: Everything was perfect from the property management to the decor of cottage and the location. We will be returning!
See All Reviews

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 $874 per night with includes Sports/Activities, Bedding/Linens, Barbecue/Outdoor Cooking, Entertainment, Child Friendly, Laundry, Parking, Private Pool, Balcony/Terrace, Security/Safety, Wellness Facilities, Fireplace/Heating, Guest Services, Air Conditioner, Internet, Kitchen, Pool, TV with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

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?

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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