Old Town Rentals USA Florida Key West Old Town

PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/Shared Heated Pool! | Cottage in Key West

9.6 (14 Reviews) |   1 Bedroom  1 Bathroom  4 Guests  Stay&Play
Old Town Cottage | PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/Shared Heated Pool!

1 Bedroom Cottage in Old Town, Key West

RELAXED DOWNTOWN LIVING...
Envelop yourself in true island living in this cute cottage just for the two of you. One of six homes in this exclusive compound located in the heart of Old Town. 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 with five other homes, 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.
MULTI MONTH RESERVATIONS...
For monthly reservations, the following fees will be added PER MONTH:
Mid-stay clean
Pool/hot tub heating fee (if applicable)
Pet fee (if applicable)
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...

PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/Shared Heated Pool! is located in Old Town. PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/Shared Heated Pool! provides accommodation, featuring Laundry, Pool, TV, among other amenities. This Cottage features Laundry, Pool, TV, to make your stay a comfortable one.

PINEAPPLE COTTAGE ~ Adorable, Updated Old Town Cottage w/Shared Heated Pool! has 1 Bedroom , 1 Bathroom, 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 Old Town has interesting places to visit. If you want to learn more about the Cottage in Old Town, 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
  • Pool
  • TV
  • View
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
  • Guest Services
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Check-in Check-in time starts at 4:00 pm contactless check-in available 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 onsite parties or group events are strictly prohibited property registration number 25230-112332 safety features at this property include a fire extinguisher and a deadbolt lock 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

Dec 2, 2024 03:12:17 AM
Summary: Great location good layout but outdated and for the price paid should be more up to date. The bed was very uncomfortable and the pillows were subpar but the interaction with the management was amazing
david p. david p.
Jul 13, 2024 09:25:30 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: 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.
Stephanie J. Stephanie J.
Feb 2, 2024 10:13:45 PM
Summary: 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: This cottage has everything you need and the location is perfect. We have rented it many times and each and every time we only had one problem.....TODD! He does his best to try and make our stay miserable.
Robin H. Robin H.
Dec 27, 2022 01:00:44 PM
Summary: 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.
Sharon W. Sharon W.
Jan 16, 2022 02:00:11 PM
Summary: 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.
Jan S. Jan S.
Dec 16, 2021 01:00:34 PM
Summary: 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.
Earl S. Earl S.
Oct 25, 2021 02:39:00 PM
Summary: 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.
Dina T. Dina T.
Feb 2, 2021 10:08:00 PM
Summary: 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!
Robin H. Robin H.
Nov 14, 2020 01:00:26 PM
Summary: 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.
Aug 7, 2020 03:04:00 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: Loved this little cottage and pool. Walking distance to everything. Clean, neat, just the right size with washer/dryer.
Chloe I. Chloe I.

FAQ's

Is this Old Town 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 Old Town cottage have a swimming pool?

Yes, this Old Town 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 Old Town cottage?

Best-rates for the Old Town cottage starts from $178 per night with includes Pool, TV, View, Kitchen, Barbecue/Outdoor Cooking, Child Friendly, Internet, Ocean View, Oceanfront, Security/Safety, Wellness Facilities, Guest Services, Air Conditioner, Balcony/Terrace, Bedding/Linens, Laundry 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 Old Town 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 Old Town cottage wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Old Town 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 Old Town cottage?

Based on the information reported by the owner or manager, the Old Town 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 Old Town cottage?

Based on the information reported by the owner or manager, details for the cancellation policy for the Old Town 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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