Entire home
JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w/ Private Pools!
Photo gallery for JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w/ Private Pools!





6 bedrooms6+ bathroomsSleeps 16
Popular amenities
Explore the area

Key West, Florida
- Duval Street8 min walk
- Ernest Hemingway Home and Museum12 min walk
- Mallory Square19 min walk
- Key West, FL (EYW-Key West Intl.)9 min drive
Rooms & beds
6 bedrooms (sleeps 16)
Bedroom 1
1 Queen Bed
Bedroom 2
1 Queen Bed
Bedroom 3
1 King Bed
Bedroom 4
1 Queen Bed
Bedroom 5
1 Queen Bed
Bedroom 6
1 King Bed
Other Space 1
1 Double Sofa Bed
Other Space 2
1 Double Sofa Bed
6 bathrooms, 1 half bathroom
Bathroom 1
Toilet
Bathroom 2
Toilet · Shower only
Bathroom 3
Toilet · Shower only
Bathroom 4
Toilet · Shower only
Bathroom 5
Toilet · Shower only
Bathroom 6
Toilet · Shower only
Bathroom 7
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Balcony
Garden
Dining area
About this property
JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w/ Private Pools!
BEDAZZLING COMPOUND...
Two delightful conch style island homes are situated on one glorious parcel in Old Town, just a stone's throw away from the magic of Duval Street and the historic Seaport. Each home features 3 bedrooms with private bathrooms, as well as their own heated pools. Quintessential charm abounds and captures your island soul, with stunning pathways through lush gardens.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
DETAILS AND AMENITIES…
Front House (PEARL): Enter the "Pearl Cottage" from its embracing wraparound porch, with ample seating and an invitation to relax and unwind in paradise. Sophisticated island style punctuates this 1279 sq. ft. home, complete with a modern and fully-stocked kitchen that overlooks a cozy living area with couch, love seat, cushioned chair and a smart TV for your viewing pleasure. There is a half bath with a stacked washer and dryer just off the living area for your convenience. These homes are equipped with Roku TV.
Back House (AMBER): Enter the newly built two-story "Amber Cottage" which boasts 1714 sq.ft. of living space. Enjoy a large, state-of-the-art kitchen that houses every appliance and tool needed for your culinary expression. This flows into the plush living and dining areas where you can unwind with loved ones and watch your favorite shows on the wall-mounted TV. Sliding doors open to the backyard oasis and a bedroom with double-entry full bath completes the downstairs space. An upstairs balcony resides on the upstairs landing and overlooks the pool.
These homes have mounted outdoor cameras but are NOT in use during guest stays.
SLEEPING ARRANGEMENTS…
Front House (PEARL): There are 3 bedrooms, two with queen beds and one with a king bed, all with private bathrooms with showers, ample storage space and TVs. A sleeper sofa resides in the living room with a powder room nearby.
Back House (AMBER): There are 3 bedrooms total. There is a downstairs queen bedroom (Murphy bed) with an office space and double-entry shower bathroom. The other two bedrooms are upstairs (one with a queen bed and the other a king) and ensuite bathrooms with showers and large closets. All upstairs bedrooms enjoy a TV for your late night down time. A sleeper sofa resides in the living room.
OUTDOOR LIVING…
Lose yourself on the stunning pathways that lead you through gorgeous lush gardens and grounds. Each home has its own private pool that can be heated in the winter months and plenty of outdoor seating for gazing at the stars and al fresco dining. The rear home (AMBER) comes with a spa and outdoor shower as a great way to end your day in Paradise.
PETS...
These homes are dog friendly only. Please include the size and breed in the comments when inquiring and booking.
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)
PARKING...
There is a driveway that will accommodate 2 vehicles.
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. 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).
BRING ALL YOUR LOVED ONES…
Two delightful conch style island homes are situated on one glorious parcel in Old Town, just a stone's throw away from the magic of Duval Street and the historic Seaport. Each home features 3 bedrooms with private bathrooms, as well as their own heated pools. Quintessential charm abounds and captures your island soul, with stunning pathways through lush gardens.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
DETAILS AND AMENITIES…
Front House (PEARL): Enter the "Pearl Cottage" from its embracing wraparound porch, with ample seating and an invitation to relax and unwind in paradise. Sophisticated island style punctuates this 1279 sq. ft. home, complete with a modern and fully-stocked kitchen that overlooks a cozy living area with couch, love seat, cushioned chair and a smart TV for your viewing pleasure. There is a half bath with a stacked washer and dryer just off the living area for your convenience. These homes are equipped with Roku TV.
Back House (AMBER): Enter the newly built two-story "Amber Cottage" which boasts 1714 sq.ft. of living space. Enjoy a large, state-of-the-art kitchen that houses every appliance and tool needed for your culinary expression. This flows into the plush living and dining areas where you can unwind with loved ones and watch your favorite shows on the wall-mounted TV. Sliding doors open to the backyard oasis and a bedroom with double-entry full bath completes the downstairs space. An upstairs balcony resides on the upstairs landing and overlooks the pool.
These homes have mounted outdoor cameras but are NOT in use during guest stays.
SLEEPING ARRANGEMENTS…
Front House (PEARL): There are 3 bedrooms, two with queen beds and one with a king bed, all with private bathrooms with showers, ample storage space and TVs. A sleeper sofa resides in the living room with a powder room nearby.
Back House (AMBER): There are 3 bedrooms total. There is a downstairs queen bedroom (Murphy bed) with an office space and double-entry shower bathroom. The other two bedrooms are upstairs (one with a queen bed and the other a king) and ensuite bathrooms with showers and large closets. All upstairs bedrooms enjoy a TV for your late night down time. A sleeper sofa resides in the living room.
OUTDOOR LIVING…
Lose yourself on the stunning pathways that lead you through gorgeous lush gardens and grounds. Each home has its own private pool that can be heated in the winter months and plenty of outdoor seating for gazing at the stars and al fresco dining. The rear home (AMBER) comes with a spa and outdoor shower as a great way to end your day in Paradise.
PETS...
These homes are dog friendly only. Please include the size and breed in the comments when inquiring and booking.
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)
PARKING...
There is a driveway that will accommodate 2 vehicles.
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. 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).
BRING ALL YOUR LOVED ONES…
Property manager
Wendy Zintsmaster & Team
Premier Host
Languages
English
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washer
Dryer
Pet-friendly
Have a question?
BetaGet instant answers with AI powered search of property information and reviews.
Similar properties

OASIS SOUTH~Stunning 5 BR/3 Ba w/ Pool!
OASIS SOUTH~Stunning 5 BR/3 Ba w/ Pool!
- Pool
- Kitchen
- Washer
- Dryer
9.8 out of 10, (7 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
Smoking
Smoking is not permitted
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
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
Property Registration Number 25230-136665
About the area
Key West
Located by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and Florida Keys Beaches. The Kite House and Sails To Rails Museum at Flagler Station are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.

Key West, Florida
What's nearby
- Duval Street - 8 min walk - 0.7 km
- Ernest Hemingway Home and Museum - 12 min walk - 1.1 km
- South Beach - 18 min walk - 1.6 km
- Mallory Square - 19 min walk - 1.6 km
- Southernmost Point - 19 min walk - 1.7 km
Getting around
Restaurants
- Cuban Coffee Queen - 7 min walk
- Pepe's Cafe - 7 min walk
- Off the Hook Grill - 8 min walk
- Dante's Key West - 7 min walk
- Harpoon Harry's - 6 min walk
Frequently asked questions
Reviews
Reviews
No reviews yet
Be the first to leave a review for this property after your stay.
About the host
Hosted by Wendy Zintsmaster & Team

Languages:
English
Premier Host
They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback