Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
Highlights
Dive into relaxation
Unwind in the top-rated pool, your perfect spot for relaxation.
Private garden
A rare find — relax in the peaceful, private garden space.
Centrally-located
You're never far from where you need to be with this convenient location.
Discover nearby landmarks
Close to Florida Keys Beaches
2 bedrooms2 bathroomsSleeps 9
Popular amenities
Shared communal pool
Onsite parking available
Pet-friendly
Kitchen
Washer
Air conditioning
Explore the area
Key West, FL
Clarence S. Higgs Memorial Beach Park
Place, Clarence S. Higgs Memorial Beach Park
9 min walk
South Beach
Place, South Beach
12 min walk
Southernmost Point
Place, Southernmost Point
14 min walk
Key West, FL (EYW-Key West Intl.)
Airport, Key West, FL (EYW-Key West Intl.)
8 min drive
Rooms & beds
2 bedrooms (sleeps 9)
Bedroom 1
1 Queen Bed
Bedroom 2
1 Twin Bed and 1 Queen Bed
Living Room 1
2 Double Sofa Beds
2 bathrooms
Bathroom 1
Toilet · Shower only
Bathroom 2
Bathtub · Toilet · Shower only
Spaces
Deck or patio
Kitchen
Office
Balcony
Garden
Dining area
About this property
Sunnyside Up - Shared Pool
Summary:
Sunnyside Up is a charming Conch-style home on United Street, just steps from Key West’s "Old Town." With an open kitchen and living area that blends seamlessly with the outdoor space, it’s perfect for relaxing or entertaining. The tropical backyard includes a shared pool with the beach and local restaurants are only a few blocks away. This prime location makes it the ideal spot for your next vacation!
The Space:
Sunnyside Up is a spacious two-bedroom, two-bathroom unit with soaring ceilings and stylish furnishings throughout. The first bedroom features a queen bed and an extra-long twin bed, along with access to the balcony, while the second bedroom offers a queen bed and its own balcony access. The living area includes two queen pull-out couches, a work-from-home space, and smart TVs with all your favorite streaming services. The galley kitchen is fully equipped for home-cooked meals and morning coffee. French doors open to the back patio, where you can enjoy a tropical oasis complete with a shared pool, dining area, lounge chairs, and a grill.
Guest Access:
Our contactless check-in procedure makes check-in easy. Guest will receive a personalized access code prior to arrival.
The Neighborhood:
This property is centrally located in Old Town, just a 10-minute walk to the beach and a 15-minute stroll to Duval Street. White Street Pier, nearby, offers volleyball nets and tennis courts. For activities close to Sunnyside Up, you can enjoy yoga classes at Shakti Yoga or visit The Local Butcher & Market. There are also plenty of excellent local restaurants nearby, including favorites like El Siboney, Frenchie’s Cafe, and Louie’s Backyard.
Getting Around:
One of the best things about staying in Key West is how close everything is. The island’s compact size makes it easy to get around, and there are plenty of fun ways to do so. If you’re not in the mood to walk, you can bike to breakfast or take a scenic ride along the water at sunset. Fury and Island Bicycles offer rentals with convenient pick-up and drop-off services. For a more relaxed pace, rent a scooter or golf cart from Minty’s and feel like you’re on island time. If you prefer a ride, Uber, Lyft, or a taxi are always available, and Pink Taxi is a reliable, affordable option for airport transfers.
Other Things to Note:
Pets are welcome! Our requirements are as follows: •40lb maximum per pet •$25/night • 2 pet maximum
Please let us know if you plan on bringing your pet.
Mid-stay cleans are available upon request.
House features a shared pool.
Private washer/dryer.
Our prices include all fees. No hidden fees.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Damages or excessive mess may incur charges. Pets under 40lbs welcome! $25/night
Important information
You need to know
Property # 9686053ha
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
About the neighborhood
Key West
Located by the sea, this apartment is in Old Town Key West, a neighborhood in Key West. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Discover the area's water adventures with fishing nearby, or enjoy the great outdoors with cycling.
Clarence S. Higgs Memorial Beach Park - 9 min walk - 0.8 km
Duval Street - 10 min walk - 0.9 km
South Beach - 12 min walk - 1.1 km
Ernest Hemingway Home and Museum - 13 min walk - 1.2 km
Southernmost Point - 14 min walk - 1.2 km
Getting around
Key West Intl. Airport (EYW) - 7 min drive
Restaurants
Dions Truman & White - 7 min walk
Sandy's Café - 6 min walk
Salute! On The Beach - 10 min walk
Rainbow Cafe (MARC) - 6 min walk
Louie's Backyard - 9 min walk
Frequently asked questions
Is Sunnyside Up - Shared Pool pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Sunnyside Up - Shared Pool?
As of Jun 23, 2026, prices found for a 1-night stay for 2 adults at Sunnyside Up - Shared Pool on Jun 24, 2026 start from $732, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking?
Onsite parking is available at the property.
What time is check-in at Sunnyside Up - Shared Pool?
Check-in begins at 4:00 PM.
What time is check-out at Sunnyside Up - Shared Pool?
Check-out is at 10:00 AM.
Where is Sunnyside Up - Shared Pool located?
Located in Old Town Key West, this apartment building is within a 10-minute walk of Key West Firehouse Museum, Florida Keys Beaches, and Duval Street. Southernmost Point and South Beach are also within 15 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Great location! Within walking distance of the Hemingway House and many restaurants. The pool was secluded and a great space to unwind from a busy day. The living room was spacious with plenty of seating for our family of 5. Parking spot is right in front of the house and was a necessary bonus for renting in Key West.
Thank you for your wonderful feedback! We're delighted you enjoyed the house and its fantastic location. We hope to welcome you back soon! - Melissa, Brightwild
Great location and very quiet, good communication made it easy to check in and out of the place.
Hunter H.
Stayed 2 nights in Sep 2024
Response from VrboOwner on Dec 31, 2024
Thank you for your positive review! We're so glad to hear you enjoyed the great location and quiet atmosphere, as well as the smooth check-in and check-out process. We appreciate your feedback and look forward to welcoming you back for another easy and enjoyable stay!
We had an awesome stay. The property managers were very responsive. This was a last minute decision and everything went smoothly. The place was clean and had everything you could need. It was a convenient location. The beds were so comfortable! Would definitely stay again.
Wendy J.
Stayed 3 nights in Aug 2025
Response from VrboOwner on Sep 3, 2025
Thank you for sharing your experience! We’re so glad to hear that your last-minute getaway turned out so well and that you found everything smooth, clean, and comfortable. It’s wonderful to know you enjoyed the location and especially the beds. We truly appreciate your kind words about our team’s responsiveness and would be delighted to welcome you back anytime!
Beautiful and clean property at an amazing location
We absolutely loved our stay, it was spacious and comfortable, and the property was stocked with all the basic amenities required for our stay. The host was friendly and was great to communicate.
Surabhi R.
Stayed 1 night in Dec 2023
Response from VrboOwner on Jan 23, 2024
Thank you for your kind review Surabhi! We are very glad to hear you enjoyed your stay! Also very happy to hear that theWe would love to host you again in the future!
There were 9 adult females and this house had plenty of space for all of us to sleep and get ready for nights out! Pool was clean and nice to lay out around. Too cold to swim in January but everything was great!
Heather M.
Stayed 3 nights in Jan 2024
Response from VrboOwner on Feb 12, 2024
Hey Heather!
Thank you for your feedback! I agree January is too cold for swimming for me as well lol! Hope we get to host you in paradise again!
Jason Brightwild!
Clean home with lovely outdoor area and pool. Just up the street from the Southernmost point... just lovely. Everything was as described...
Peggy S.
Stayed 7 nights in Dec 2024
Response from VrboOwner on Jan 21, 2025
Thank you for your wonderful review! We're so glad you enjoyed the clean home, outdoor area, and pool. It's great to hear everything met your expectations. We hope to host you soon again! - Melissa, Brightwild
Verified
8/10 Good
Jeffrey B.
Mar 18, 2026
Liked: Cleanliness, check-in, communication
The shower up stairs would not drain and one of the pull out couch’s should not be considered a pull out couch
A very cozy place and a very quiet area, we did not enjoy the swimming pool because we saw it a bit dirty... the patio was very nice although we did not enjoy it either because we spent most of the time outside the house, but I would come back... thanks for everything .
Sugeiry R.
Stayed 4 nights in Aug 2022
Response from VrboOwner on Sep 13, 2023
We are glad to hear you enjoyed the property, Sugeiry! Next time you stay with us, please reach out if you feel the pool could be cleaner. Our team is more than happy to meet and exceed all guests expectations and would have come to clean it for you. Thank you for choosing One of One and for the positive review! Cheers, One of One
There was one assigned parking spot but we were able to street park our 2nd car for free. There were plenty of beach towels. Enough dishes that our party of 5 only ran the dishwasher every other day. Lots of patio seating. I asked for and received extra supplies (coffee pods and paper towels) promptly. I asked if decaf was available and was pleasantly surprised when there was a stash waiting for me. I liked there was a recycling can on site. I didn’t use them, but there was a cabinet with about 50 different games to play for families.