Entire home
Work from home in this slice of Islamorada paradise!
Photo gallery for Work from home in this slice of Islamorada paradise!





Reviews
9.89.8 out of 10
Exceptional
Highlights
- Firepit availableOne of the few properties with a dedicated outdoor firepit.
- Discover nearby landmarksNear Anne's Beach
Popular amenities
- Onsite parking available
- Kitchen
- Washing machine
- Air-conditioning
- Barbecue
- Balcony
Explore the area

Islamorada, FL
- Sunset Drive BeachPlace, Sunset Drive Beach3 min walk
- Anne's BeachPlace, Anne's Beach14 min walk
- Robbie’s of IslamoradaPlace, Robbie’s of Islamorada5 min drive
- Marathon, FL (MTH-Florida Keys Marathon)Airport, Marathon, FL (MTH-Florida Keys Marathon)33 min drive
Rooms & beds
2 bedrooms (sleeps 5)
Bedroom 1
1 King Bed
Bedroom 2
1 Single Bunk Bed
1 bathroom
Bathroom 1
Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
Dining area
About this property
Work from home in this slice of Islamorada paradise!
Come visit this tropical, remodeled vacation home and get a taste of all Islamorada has to offer with cozy, modern and clean outdoor and indoor living! Perfect for couples on a romantic getaway, solo-travelers looking for a work-from-home retreat or families enjoying time by the sea together.
This home offers 2 bedrooms, 1 full bath, fully stocked kitchen, living and dining area with plenty of outdoor living space for the whole family. Park in the covered car port and enter your island oasis overlooking the canal. Sit beneath the tiki where you can relax, barbecue and greet passing manatees. Take a nap on one of our hammocks and hear the rustling palm trees sway in the island breeze. Chat over snacks and spirits under the second tiki and bar stools. The outdoor area has 60' of dockage and a fish cleaning table.
Upstairs you'll find a large outdoor deck — fit with another hammock, seating and dining area. Once inside, you'll enter through the living room, which has a nook with bar stools opening into the kitchen. The fully stocked kitchen is fit with stainless steel appliances and an eat-in counter. The dining table expands to comfortably seat four. By the kitchen, overlooking the front driveway is another balcony — perfect for enjoying a morning coffee or afternoon snack. Through the hallway, you'll come across the bathroom, which has a large shower, brand new LG washer-dryer unit and a vanity area. Across from the bathroom is the second bedroom — fit with a bunk bed and tumble for three. The second bedroom has a desk and access to the front balcony, which overlooks the quiet street and front yard. The master bedroom is tucked away at the end of the hall. It has a king bed and attached seating area, perfect for reading a book or working from home. The master bedroom overlooks the backyard and canal.
The home has reliable WIFI connection throughout (even accessible in the backyard); our daughter has consistently worked from home and taken classes remotely via Zoom with the WIFI connection. It is stronger than our internet connection on the mainland. There are smart TV's in all bedrooms and in the living room.
The house is located on a quiet, residential street. The street is dimly lit at night to protect sea turtle hatchlings that may be nearby, making perfect viewing conditions for star gazing.
The home is within walking distance to Anne's Beach (best public beach in Islamorada) or 3 minute drive by car. Across from Anne's Beach is a public fishing bridge on the bayside, which is great for watching sunsets after dinner. The home is also walking distance to Caloosa Cove Marina, where you can rent or charter a boat, grab goodies at the convenience store, or eat Cuban cuisine at Habano's Oceanfront Dining (a must for a South Florida visit!). Bikes available upon request at no extra charge.
This vacation home is not pet friendly. Additionally, no smoking is allowed on premises (inside or outside of house). Unregistered guests are not allowed to stay overnight at the home; reservation is subject to cancellation if unregistered guests are found staying on property. To prevent this, a copy of identification will be required of registered guests before each stay begins. A ring camera is located on exterior of home.
Our family loves Islamorada and has made the best memories on Lower Matecumbe Key and hope The We Key House is the perfect home-base for your trip! Please do not hesitate to reach out with any questions or concerns. We are happy to assist with recommendations on activities and dining nearby.
This home offers 2 bedrooms, 1 full bath, fully stocked kitchen, living and dining area with plenty of outdoor living space for the whole family. Park in the covered car port and enter your island oasis overlooking the canal. Sit beneath the tiki where you can relax, barbecue and greet passing manatees. Take a nap on one of our hammocks and hear the rustling palm trees sway in the island breeze. Chat over snacks and spirits under the second tiki and bar stools. The outdoor area has 60' of dockage and a fish cleaning table.
Upstairs you'll find a large outdoor deck — fit with another hammock, seating and dining area. Once inside, you'll enter through the living room, which has a nook with bar stools opening into the kitchen. The fully stocked kitchen is fit with stainless steel appliances and an eat-in counter. The dining table expands to comfortably seat four. By the kitchen, overlooking the front driveway is another balcony — perfect for enjoying a morning coffee or afternoon snack. Through the hallway, you'll come across the bathroom, which has a large shower, brand new LG washer-dryer unit and a vanity area. Across from the bathroom is the second bedroom — fit with a bunk bed and tumble for three. The second bedroom has a desk and access to the front balcony, which overlooks the quiet street and front yard. The master bedroom is tucked away at the end of the hall. It has a king bed and attached seating area, perfect for reading a book or working from home. The master bedroom overlooks the backyard and canal.
The home has reliable WIFI connection throughout (even accessible in the backyard); our daughter has consistently worked from home and taken classes remotely via Zoom with the WIFI connection. It is stronger than our internet connection on the mainland. There are smart TV's in all bedrooms and in the living room.
The house is located on a quiet, residential street. The street is dimly lit at night to protect sea turtle hatchlings that may be nearby, making perfect viewing conditions for star gazing.
The home is within walking distance to Anne's Beach (best public beach in Islamorada) or 3 minute drive by car. Across from Anne's Beach is a public fishing bridge on the bayside, which is great for watching sunsets after dinner. The home is also walking distance to Caloosa Cove Marina, where you can rent or charter a boat, grab goodies at the convenience store, or eat Cuban cuisine at Habano's Oceanfront Dining (a must for a South Florida visit!). Bikes available upon request at no extra charge.
This vacation home is not pet friendly. Additionally, no smoking is allowed on premises (inside or outside of house). Unregistered guests are not allowed to stay overnight at the home; reservation is subject to cancellation if unregistered guests are found staying on property. To prevent this, a copy of identification will be required of registered guests before each stay begins. A ring camera is located on exterior of home.
Our family loves Islamorada and has made the best memories on Lower Matecumbe Key and hope The We Key House is the perfect home-base for your trip! Please do not hesitate to reach out with any questions or concerns. We are happy to assist with recommendations on activities and dining nearby.
Add dates for prices
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Classic 2 bedroom, 2 Bath Islamorada Home with Dockage
Matecumbe
Classic 2 bedroom, 2 Bath Islamorada Home with Dockage
Matecumbe
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)

Keys Getaway – 2 Bikes, Heated Pool, Small Beach & Sunset Dock Views
Islamorada
Keys Getaway – 2 Bikes, Heated Pool, Small Beach & Sunset Dock Views
Islamorada
- Ocean view
- Pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (11 reviews)
10/10
Exceptional
(11 reviews)

House in Islamorada, in exclusive Venetian Shores.
Venetian Shores
House in Islamorada, in exclusive Venetian Shores.
Venetian Shores
- Kitchen
- Pet-friendly
- Air-conditioning
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)

Beautiful, Spacious, Single Story Home - Islamorada
Venetian Shores
Beautiful, Spacious, Single Story Home - Islamorada
Venetian Shores
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (3 reviews)
10/10
Exceptional
(3 reviews)

3-bedroom, 3-bath Canal front home with private pool in Islamorada, Florida Keys
Matecumbe
3-bedroom, 3-bath Canal front home with private pool in Islamorada, Florida Keys
Matecumbe
- Pool
- Kitchen
- Washing machine
- Dryer

Beautiful 2/2 Islamorada Home Directly on Florida Bay (28 Day Minimum Rental)
Matecumbe
Beautiful 2/2 Islamorada Home Directly on Florida Bay (28 Day Minimum Rental)
Matecumbe
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (7 reviews)
10/10
Exceptional
(7 reviews)

"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!"
Matecumbe
"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!"
Matecumbe
- Ocean view
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (20 reviews)
10/10
Exceptional
(20 reviews)

Peacock Shores Islamorada - Vacation On The Beach!
Islamorada
Peacock Shores Islamorada - Vacation On The Beach!
Islamorada
- Ocean view
- Pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (46 reviews)
10/10
Exceptional
(46 reviews)

Water Front 3/3 Family and Boat Friendly Home, Great Views
Matecumbe
Water Front 3/3 Family and Boat Friendly Home, Great Views
Matecumbe
- Spa pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (21 reviews)
10/10
Exceptional
(21 reviews)

ISLAMORADA WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CONTACT OWNER
Matecumbe
ISLAMORADA WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CONTACT OWNER
Matecumbe
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (57 reviews)
10/10
Exceptional
(57 reviews)

Large Waterfront Home with 80 ft Dockage and Boat Lift with Pool In Islamorada
Matecumbe
Large Waterfront Home with 80 ft Dockage and Boat Lift with Pool In Islamorada
Matecumbe
- Ocean view
- Pool
- Kitchen
- Washing machine
9.8 out of 10, Exceptional, (10 reviews)
9.8/10
Exceptional
(10 reviews)

CHARMING WATERFRONT OCEANSIDE CANAL HOME-LARGE PROTECTED DOCKAGE-WiFi-SMART TVs.
Matecumbe
CHARMING WATERFRONT OCEANSIDE CANAL HOME-LARGE PROTECTED DOCKAGE-WiFi-SMART TVs.
Matecumbe
- Ocean view
- Kitchen
- Washing machine
- Dryer
9.6 out of 10, Exceptional, (91 reviews)
9.6/10
Exceptional
(91 reviews)

5 Star Modern Oceanfront Islamorada Townhome on the Beach!
Islamorada
5 Star Modern Oceanfront Islamorada Townhome on the Beach!
Islamorada
- Ocean view
- Pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (112 reviews)
10/10
Exceptional
(112 reviews)

Canal front home in Venetian Shores. Perfect for families . A boater's paradise!
Venetian Shores
Canal front home in Venetian Shores. Perfect for families . A boater's paradise!
Venetian Shores
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)

New saltwater pool, pet friendly, waterfront house with dock
Matecumbe
New saltwater pool, pet friendly, waterfront house with dock
Matecumbe
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (5 reviews)
10/10
Exceptional
(5 reviews)
