PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!

1 bedroom, iron/ironing board, free WiFi, bed sheets

4.9

Outstanding(13 Reviews)

Cottage in Key West, FL

4 guests · 2 bedrooms · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating

Includes essentialsPool, Kitchen or Kitchenette, Air conditioner and more

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this cottage rental

RELAXED DOWNTOWN LIVING...
Envelop yourself in true island living in this cute cottage just for the two of you. Located one block from Duval with charming porch and shared heated pool. Walk or stroll to dining, night life, galleries, shopping, and be at fabulous Ft. Zachary beach beach in minutes.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

FURNISHINGS...
Cozy one queen bedroom and one bath. Great open floor plan with hardwood floors, plenty of Key West sunshine and blue skies through the large windows. Flat screens in the living and bedroom. Well stocked kitchen to use your culinary skills. Washer and dryer. Sofa sleeper in the living room is also available.

OUTSIDE LIVING...
Beautiful heated pool and waterfall. The pool and courtyard area is shared, but it will feel like your own quiet piece of paradise with little to no traffic.

NEIGHBORHOOD ATTRACTIONS...
Stroll through Bahama Village located in downtown Key West; aptly named because of it's many inhabitants that are of Bahamian decent. This lively neighborhood offers many popular restaurants such as Blue Heaven, Santiago's Bodega and La Creppiere. You can also find many small boutiques filled with treasures made by local artisans, some specialty wares and even antiques. Directly across from Hemingway's Home, Moon Dog restaurant and steps from the Southernmost Point.

PARKING...
This home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.

PETS...
No pets allowed.

BOOKING DATES...
This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.

CONCIERGE SERVICES...
Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!

CANCELLATION...
Bookings canceled at least 90 days before the start of stay will receive a 100% refund.

Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).

INDULGE IN DOWNTOWN LIVING...

Amenities

Pool

Air conditioner

Kitchen or Kitchenette

Internet / Wifi

Laundry

Balcony or Patio

Dishwasher

Map of Key West, FL

Nearby attractions

The Key West Butterfly and Nature Conservatory

0.7 mi

Mallory Square

1.1 mi

Southernmost Point of the Continental U.S.A.

0.7 mi

The Hemingway Home and Museum

0.1 mi

PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!

4.9

Outstanding(13 Reviews)

Cottage in Key West, FL

4 guests · 2 bedrooms · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating

Includes essentialsPool, Kitchen or Kitchenette, Air conditioner and more

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this cottage rental

Amenities

Pool

Air conditioner

Kitchen or Kitchenette

Internet / Wifi

Laundry

Balcony or Patio

Dishwasher

Map of Key West, FL

Nearby attractions

The Key West Butterfly and Nature Conservatory

0.7 mi

Mallory Square

1.1 mi

Southernmost Point of the Continental U.S.A.

0.7 mi

The Hemingway Home and Museum

0.1 mi

Reviews

4.9

Outstanding(13 Reviews)

4.9

Jul 2024

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: Absolutely cannot beat the location ... on the less busy end of Duval only a few blocks from the Southernmost Point. The cottage was just the right size for 2 people, was clean and well appointed. Walking distance to so many restaurants and lots of people watching from the front porch. A bonus was we got to meet several of the neighbors (Paul/Emily/Todd/David/Less) around us and they were all great - happy hour to celebrate Paul's birthday month was one of our best nights). Todd was super helpful and answered any question we had about the house and neighborhood. Communication with Whitney at Best of Key West Rentals was always prompt and helpful. Highly recommend.

4.9

Feb 2024

4.9

Dec 2022

Overall great. Loved location. Friendly locals enhanced experience. Only complaint was with mid stay clean that was required. Suggestions for mid clean- Should be different in some ways than final clean - - - - I’d set time on coffee pot so could set up night before and have coffee ready in am. Was unplugged during clean. Making me have to reset time again. Blender/toaster set out on counter to use without having to get down on floor to retrieve them from small cabinet between stove and wall. Were put away. So had to get out again. I’d brought a kitchen sponge from home to use for hand washing a few of the dishes. I’d put it in dishwasher flatware holder to cleanse with the dishes like I do at home. Dishwasher emptied and my sponge gone. No reason to get rid of it mid clean. Also think if a mid visit cleaning is required a small safe should be provided for valuables- passport, jewelry, cash, credit cards etc.

4.9

Jan 2022

My issue was the location of the pool I had been so looking forward to. It is right outside and in the walking pathway of the other cottages. All cottages are located almost on top of each other.

4.9

Jan 2022

My issue was the location of the pool I had been so looking forward to. It is right outside and in the walking pathway of the other cottages. All cottages are located almost on top of each other.

4.9

Jan 2022

Location was just what I wanted. The cottage itself was wonderful.

Location was just what I wanted. The cottage itself was wonderful.

My issue was the location of the pool I had been so looking forward to. It is right outside and in the walking pathway of the other cottages. All cottages are located almost on top of each other.

4.9

Dec 2021

The location was perfect. The cottage was clean, well maintained and very comfortable. when we had a small thing that needed seeing to, the manager responded the same day.

4.9

Dec 2021

Recommended

Recommended

The location was perfect. The cottage was clean, well maintained and very comfortable. when we had a small thing that needed seeing to, the manager responded the same day.

4.9

Oct 2021

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very unhappy with the location. I was very satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: The cottage is exactly as described. Super cute and practical. Brian, the property manager, was excellent. Above and beyond service. Sadly, you will be living next door to a very unwell man named Todd. He’s the only downfall to the property.

4.9

Oct 2021

Great place / attentive management / unhinged neighbor

Great place / attentive management / unhinged neighbor

4.9

Feb 2021

Pineapple Cottage

Pineapple Cottage

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location to sit on porch and people watch!

4.9

Nov 2020

Great location and property making walking around and exploring Key West very easy! Brain, property manager, and team were very helpful, responsive and accessible. Thank you.

4.9

Oct 2020

Pineapple Cottage, Key West

Pineapple Cottage, Key West

Great location and property making walking around and exploring Key West very easy! Brain, property manager, and team were very helpful, responsive and accessible. Thank you.

4.9

Aug 2020

Wonderful

Wonderful

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: Loved this little cottage and pool. Walking distance to everything. Clean, neat, just the right size with washer/dryer.

4.9

Apr 2020

Great Location

Great Location

4.9

Feb 2020

Pineapple Cottage 2020

Pineapple Cottage 2020

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our stay at Pineapple Cottage has always been great and the rental people we have dealt with have been wonderful. We only have one complaint regarding this years stay. The couple that occupied the cottage next to us were heavy smokers. Even though they never smoked on the property, their car was parked out front and they sat in it with the doors open and smoked or stood on the sidewalk in front of their cottage and smoked constantly. It was unpleasant for us to sit on the porch (which we love to do) because there was constant cigar and cigarette smoke. They also enjoyed their alcohol to the point of falling down on the sidewalk and having a stranger assist them back on the porch. We enjoy this property so much, but this year was less pleasant because of them.

4.9

Dec 2016

Exceeded our expectations. Very well presented.

Exceeded our expectations. Very well presented.

Arrival and departure was extremely easy, we were given the door code and did a self check in and when we left, we basically left the cottage the way we found it and closed the door. A few days after we arrived the garburator started to leak, and also the BBQ grill ran out of propane. We contacted Truman properties and both were fixed immediately. When we walked into the cottage it was exactly as it appeared on the website which was very satisfying. The location of the property was basically in the middle between the harbor and the beaches, each being about a 10 minute walk in either direction and it was just one block from Duval so that we didn’t hear or see all the action, but were close enough to wander over. We did not rent a car for our month’s stay and really did not need one to get around. We rented bicycles for a few days which was nice to give our feet a rest and to see just a little bit more of the island. There were many great restaurants and happy hours to take in. The weather was amazing every day, and there were also many events happening each week while we were there. I would recommend this cottage to experience all that Key West has to offer.

4.9

Apr 2015

Heart of Everything? You bet!

Heart of Everything? You bet!

818-2 Whitehead really is in the heart of it all. 1/2 block from Hemingway House, 1 block from Blue Heaven, and 2 blocks from Green Parrot. We were there for two months and couldn't have been happier with it all. Particularly the staff at the rental office -- always helpful and friendly. Parking can be a bit tough some times, but with the location, and our bicycles, we would sometimes go a week or more with just walking wherever we wanted to go. A great place to relax on the front porch and let the world (or at lease the tourists) go by.

FAQs

How much does this cottage cost compared to others in Key West?

The average price for a rental in Key West is $656 per night. This rental is $405 less expensive than the average.

Is parking included with this cottage?

Parking is not specified as an available amenity at PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this cottage?

Yes, a swimming pool is available for use at PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!. Enjoy the water!

Is PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool! pet friendly?

Unfortunately, this cottage is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!?

We found 8 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and laundry.

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PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!

Cottage in Key West, FL

Reasons to book

About this cottage rental

Amenities

Map of Key West, FL

Nearby attractions

PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!

Cottage in Key West, FL

Reasons to book

About this cottage rental

Amenities

Map of Key West, FL

Nearby attractions

Reviews

FAQs

How much does this cottage cost compared to others in Key West?

Is parking included with this cottage?

Is there a pool at this cottage?

Is PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool! pet friendly?

What amenities are available at PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!?

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