Entire home
NEW! Stunning Oceanfront Estate with Private Pool ~ Beach - 2026+ Calendar only
Photo gallery for NEW! Stunning Oceanfront Estate with Private Pool ~ Beach - 2026+ Calendar only
6 bedrooms6+ bathroomsSleeps 14436.6 sq m
Popular amenities
Explore the area
Islamorada, FL
- Robbie’s of Islamorada10 min walk
- Bud n' Mary's Dive Center3 min drive
- Anne's Beach4 min drive
- Marathon, FL (MTH-Florida Keys Marathon)32 min drive
Rooms & beds
6 bedrooms (sleeps 14)
Bedroom 2
1 King Bed
Bedroom 3
1 King Bed
Bedroom 4
1 King Bed
Bedroom 5
4 Single Beds
Bedroom 6
1 King Bed and 1 Crib
Living Room 1
2 Single Sofa Beds
Master
+1
1 King Bed, 1 Crib, 1 Child Bed and 2 Single Beds
6 bathrooms, 1 half bathroom
Bathroom 1
Towels provided · Bathtub or shower · Toilet · Jetted bathtub · Hair dryer
Bathroom 2
Towels provided · Toilet · Shower only · Hair dryer
Bathroom 3
Towels provided · Bathtub or shower · Bathtub · Toilet · Hair dryer
Bathroom 4
Towels provided · Toilet · Shower only · Hair dryer
Bathroom 5
Towels provided · Bathtub or shower · Bathtub · Toilet · Hair dryer
Bathroom 6
Towels provided · Toilet · Shower only · Hair dryer
Bathroom 7
Towels provided · Toilet
Spaces
Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden
Dining area
About this property
NEW! Stunning Oceanfront Estate with Private Pool ~ Beach - 2026+ Calendar only
License # 204.
| ** 3 payment schedule available** | No Pet Charges | No security deposit |
SATURDAY TO SATURDAY ONLY BOOKINGS
** This Premier host is listed under #9250358ha for calendar year 2025**
Escape to this welcoming house in picturesque Islamorada. This fantastic property boasts 6 bedrooms, including 5 king beds, 4 custom bunks, 2 cribs, a toddler bed, and more. With 6.5 bathrooms offering amenities like a jetted bathtub, this place is perfect for large groups or families. The Master bedroom offers two additional twin beds on the sun porch and a nursery nook with a crib and toddler bed, making a wonderful family suite.
The Last Resort Too is our sister home to the original Last Resort, offering our ability to cater to larger families and groups. Set on over two acres of prime oceanfront land, complete with a heated swimming pool, 200 ft of beach, a walking/fishing dock, and nestled behind privacy gates, you will feel right at home in this exclusive enclave of Islamorada.
This house can book up to two years in advance and is already taking bookings for both 2026 & 2027.
** The owner who has been part of VRBO since 2004, will be managing the home directly from 2026. As an already established listing on VRBO, reviews do not transfer to this 2026 listing. If interested in booking, please request them or go to our property manager's existing listing on VRBO #9250258ha.
| ** 3 payment schedule available** | No Pet Charges | No security deposit |
SATURDAY TO SATURDAY ONLY BOOKINGS
** This Premier host is listed under #9250358ha for calendar year 2025**
Escape to this welcoming house in picturesque Islamorada. This fantastic property boasts 6 bedrooms, including 5 king beds, 4 custom bunks, 2 cribs, a toddler bed, and more. With 6.5 bathrooms offering amenities like a jetted bathtub, this place is perfect for large groups or families. The Master bedroom offers two additional twin beds on the sun porch and a nursery nook with a crib and toddler bed, making a wonderful family suite.
The Last Resort Too is our sister home to the original Last Resort, offering our ability to cater to larger families and groups. Set on over two acres of prime oceanfront land, complete with a heated swimming pool, 200 ft of beach, a walking/fishing dock, and nestled behind privacy gates, you will feel right at home in this exclusive enclave of Islamorada.
This house can book up to two years in advance and is already taking bookings for both 2026 & 2027.
** The owner who has been part of VRBO since 2004, will be managing the home directly from 2026. As an already established listing on VRBO, reviews do not transfer to this 2026 listing. If interested in booking, please request them or go to our property manager's existing listing on VRBO #9250258ha.
Property manager
Michele Rosborough
Add dates for prices
Amenities
Pool
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
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House Rules
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
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
This property uses eco-friendly cleaning products
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
We should mention
This property does not have any lifts
About the area
Islamorada
Located in Matecumbe, a neighbourhood in Islamorada, this holiday home is near theme parks and on the beach. Indian Key Historic State Park and Hurricane Monument are local landmarks, and the area's natural beauty can be seen at Windley Key Fossil Reef Geological State Park and Sunset Drive Beach. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Islamorada, FL
What's nearby
- Robbie’s of Islamorada - 10 min walk - 0.9 km
- Indian Key Historic State Park - 18 min walk - 1.6 km
- Sunset Drive Beach - 3 min drive - 4.0 km
- Bud n' Mary's Dive Center - 3 min drive - 4.6 km
- Anne's Beach - 4 min drive - 5.6 km
Getting around
Restaurants
- Robbie's of Islamorada - 10 min walk
- Lorelei Restaurant & Cabana Bar - 7 min drive
- Lazy Days Restaurant - 4 min drive
- Islamorada Fish Company - 6 min drive
- Square Grouper - 5 min drive
Frequently asked questions
Reviews
Reviews
No reviews yet
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About the host
Hosted by Michele Rosborough
Greg and Michele are married with 4 children in total: 2 out of College, the 3rd a Junior, and a 10th Grader. We live in Chapel Hill, North Carolina, which is a suburb of Raleigh. We have owned this home in Islamorada since 2021; we also own another estate 300 yards south called The Last Resort since 2000 that has been listed on VRBO since 2004. The VRBO # is 311833ha; prior to that, we owned a condo in Truman Annex in Key West, FL, since 1993.
Greg worked in Finance for IBM/Lenovo & Cisco and lived/worked in England from 1998-2000 and Dublin, Ireland from 2000-2004 with IBM. He recently retired and enjoys spending time with my family, traveling, Islamorada, playing sports, and listening to boring financial shows and the History Channel. Michele is from Dublin- Ireland, a retired Management Consultant, an avid world traveler for work and recreation, and a major hockey fan.
We are happy to answer questions.
Greg worked in Finance for IBM/Lenovo & Cisco and lived/worked in England from 1998-2000 and Dublin, Ireland from 2000-2004 with IBM. He recently retired and enjoys spending time with my family, traveling, Islamorada, playing sports, and listening to boring financial shows and the History Channel. Michele is from Dublin- Ireland, a retired Management Consultant, an avid world traveler for work and recreation, and a major hockey fan.
We are happy to answer questions.
Why they chose this property
Close proximity to local shops, dining, and Marinas. This is one of the largest property sites in Islamorada, with a private 200 ft. sand beach and a private walking/fishing dock. We purchased this home primarily due to the size of the oceanfront land with an expansive view and a predominantly ground-level home with lots of windows for viewing the beautiful surroundings. One of the more important considerations was the safety of kids. It is perfect for reconnecting with friends and family away from the hustle and bustle of life.
What makes this property unique
We like quiet privacy. This larger home is set on two acres and is 6 bed/6.5 bath. One of those beds/baths is in a separate but attached guest cottage, perfect for couples seeking peace and quiet.
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