A rare find — relax in the peaceful, private garden space.
Discover nearby landmarks
Near Florida Keys Beaches
5 bedrooms5+ bathroomsSleeps 10
Popular amenities
Private pool
Onsite parking available
Pet-friendly
Kitchen
Washer
Air conditioning
Explore the area
Key West, FL
Florida Keys Beaches
Place, Florida Keys Beaches
2 min walk
Clarence S. Higgs Memorial Beach Park
Place, Clarence S. Higgs Memorial Beach Park
8 min walk
Smathers Beach
Place, Smathers Beach
9 min walk
Key West, FL (EYW-Key West Intl.)
Airport, Key West, FL (EYW-Key West Intl.)
7 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
2 Twin Beds
Bedroom 4
1 King Bed
Bedroom 5
1 King Bed
5 bathrooms, 1 half bathroom
Bathroom 1
Toilet · Shower only
Bathroom 2
Toilet · Shower only
Bathroom 3
Toilet · Shower only
Bathroom 4
Toilet · Shower only
Bathroom 5
Bathtub · Toilet · Shower only
Bathroom 6
Toilet
Spaces
Deck or patio
Kitchen
Balcony
Garden
Dining area
About this property
POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!
EXQUISITE MODERN FAMILY COMPOUND... If a large home with all the modern luxuries is a must for your next island getaway, look no further than this sprawling beauty that's located in Midtown Key West. Your crew will delight in the 5 fabulous ensuite bedrooms that will wow you with their custom design and spaciousness, setting the scene for a magical retreat. You are close to beaches, parks, the popular White Street Pier and comfortably close to all the fun and excitement of Duval Street. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
DETAILS AND AMENITIES... Gather with the gang on the ground floor entertaining space for outdoor dining fun at your table for 10, featuring a huge tv for movie nights, cushioned sitting space for animated conversations and a billiard game area. After a day of outdoor adventures, travel up the stairs to the first floor that is beautifully decorated with a contemporary flair mixed with island whimsy. The Great Room has a wonderful open flow that creates a sense of spaciousness and domestic functionality. A large sectional with giant tv offer a cool embrace and a promise of deep relaxation with your loved ones. Concoct your culinary favorites in the chef-inspired kitchen that is brimming with every modern convenience you would need to feed your crew in style. A dining table for 8 and island seating for 4 offer ample seating at mealtimes. A washer/dryer and powder room are also located on the first floor and a laundry room resides on the third floor. This home is equipped with Youtube TV streaming.
SLEEPING ARRANGEMENTS... A stunning king bedroom resides on the first floor. Second floor: The first bedroom houses a queen bed and a shower/tub combination bathroom, The second bedroom has 2 twin XL beds that can convert to a king upon request and a glass-door rain shower bathroom. Third floor: The first bedroom features a king bed, desk area and giant glass-door rain shower bathroom. The second bedroom offers a king bed and a giant glass shower and tub inside it. All bedrooms feature tvs, closets and clothing dressers.
OUTDOOR LIVING... Throw open the french doors in the first floor living area to immerse yourself in the lush backyard oasis that greets you with a sparkling pool (can be heated in the winter months) under sultry island breezes and soft swaying foliage surrounding cozy seating areas. Disconnect and refresh in your little piece of Key West heaven. Grill out your fresh catch of the day and rinse off in the outdoor shower before your retreat on the town!
PARKING.... This has off street parking for 2 vehicles.
PETS... Dogs (NO CATS) are considered and a pet fee is required. Please include the size / breed in the comments when inquiring.
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)
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!
BOOKING DATES... This home is only available as a monthly rental (28 night min). 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.
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).
COME STAY A WHILE...
Our prices include all fees. No hidden fees.
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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 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
About the neighborhood
Key West
Located by the sea, this vacation home is in Midtown, 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. Key West Butterfly and Nature Conservatory and MLK Community Pool & Community Center 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.
Clarence S. Higgs Memorial Beach Park - 8 min walk - 0.7 km
Smathers Beach - 9 min walk - 0.8 km
Key West Naval Station - 9 min walk - 0.8 km
Duval Street - 7 min drive - 2.0 km
Getting around
Key West Intl. Airport (EYW) - 5 min drive
Restaurants
Circle K - 16 min walk
Dions Truman & White - 19 min walk
Sandy's Café - 18 min walk
Taco Bell - 3 min drive
Salute! On The Beach - 11 min walk
Frequently asked questions
Does POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching! have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!?
As of Jun 12, 2026, prices found for a 1-night stay for 2 adults at POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching! on Aug 1, 2026 start from $582, 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.
Is POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching! pet-friendly?
Yes, pets are allowed at this property.
How much is parking?
Onsite parking is available at the property.
What time is check-in at POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!?
Check-in begins at 4:00 PM.
What time is check-out at POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!?
Check-out is at 10:00 AM.
Where is POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching! located?
Located in Midtown, this vacation home is within 1 mi (2 km) of Clarence S. Higgs Memorial Beach Park and Florida Keys Beaches. Duval Street and Southernmost Point are also within 2 mi (3 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Incredible stay. The house is perfect and the support provided is fantastic. Highly recommend.
Tom C.
Stayed 29 nights in Apr 2026
Response from VrboOwner on May 18, 2026
We’re so glad you had a great time with us Tom. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
From a partner site
10/10 Excellent
denise m.
May 3, 2024
Dream Vacation
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:
We rented "Pocketful of Sunshine" for the month of April. We had our adult children and their families and Mom/Grandma come down for 10 days followed by my husband's brother and his wife and sister and Mom stayed through 8 days and then college buddies came down for 5 days. WOW! The house was perfect for all our gatherings!! 5 Gorgeous bedrooms with beautiful ensuite bathes, a great pool area with beautiful sitting area that was wonderful for morning coffee with everyone. We had family movie night in the living room with popcorn a few evenings and great family breakfasts on the huge gas stove. It is a bit tight if you want to sit at the island with the couch directly behind but we mostly sat at the table. Another plus was the full laundry room with sink and ironing board on the 3rd floor and another stacked washer & dryer on the main level. The house is only 5 minutes from the airport, less than 5 minutes to Smathers Beach and less than 5 minutes to Salute Restaurant on the Beach (sister restaurant to Blue Heaven). Farmer's Market on Sunday in a park less than 5 minutes away and Duval St. is about 10 minutes away (by golf cart) Everyone in all our groups loved the house! They had their own private space in their large beautiful bedrooms which included a TV in each bedroom. Plus each floor has its own thermostat and ceiling fans in each bedroom. We also enjoyed the covered patio area that included a large table and chairs, sitting area and game area. The one time it rained, everyone enjoyed the covered area and the fun continued. All in all, we had a great time here! In Grandma's words, It was the vacation of her dreams! Note: the few times we had a question, Dan (property manager) responded immediately and that was great! Note: I paid for an extra complete house cleaning (including bedding & towels) in between groups so I didn't spend a vacation day cleaning and they did a fantastic job! Well worth the money charged!
denise m.
Response from VrboOwner on May 4, 2024
Thank you for your incredible review Denise! We are so thrilled to hear how much you loved this Key West retreat and we are looking forward to hosting you again next time you visit the island. Thank you for being our guest!
About the host
Hosted by Wendy Zintsmaster & Team
Languages:
English
Premier Host
They consistently provide great experiences for their guests