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Booking heavily for 2027 and 2028! - Stunning Oceanfront Estate - Private Pool

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A spacious room with large windows overlooking a beach, a television, and a comfortable seating area.
A bedroom with a large window overlooking a beach with palm trees and the ocean.
A wooden deck with a white railing overlooking a beach and a pool.
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.
A beachfront property with a dock, clear water, and palm trees.

Reviews

10 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • On the beach
    A rare beachfront property in the area - enjoy direct access to the sand and sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
6 bedrooms6+ bathroomsSleeps 14

Popular amenities

  • On beach
  • Private pool
  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine

Explore the area

View in a map
Islamorada, FL
  • Place, Robbie’s of Islamorada
    ‪1 min drive‬
  • Place, Indian Key Historic State Park
    ‪2 min drive‬
  • Place, Sunset Drive Beach
    ‪4 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪37 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
Number of living rooms
Outdoor play area
Garden
Dining area

About this property

Booking heavily for 2027 and 2028! - Stunning Oceanfront Estate - Private Pool

License # 204.

| ** 3 payment schedule available** | No Pet Charges | No security deposit |
SATURDAY TO SATURDAY ONLY BOOKINGS

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 the 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, and a walking/fishing dock. Nestled behind privacy gates, you will feel right at home in this exclusive enclave of Islamorada. *Please note: V-boats do not have clearance for this dock; flat bottom and pontoons only. * Please check with us for V-Boat accommodations.

This house can book up to two years in advance and is already taking bookings for both 2027 and 2028.

** 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 new 2026 listing.

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  • Kitchen
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10.0 out of 10, Exceptional, (103 reviews)
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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
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Smoking

Smoking is not permitted
House should be left in the condition it was found BAR normal cleaning.
Refunds are given due to cancelation 60 days before arrival. If canceled inside 60 days, we will refund if we can get a replacement guest.
All guests are required to sign the owner contract, which will be emailed to your address on file with VRBO

Important information

You need to know

Property # 4357870vb
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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property

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. Consider Lorelei Restaurant & Cabana Bar for a night out or MoradaWay Arts & Cultural District if you're travelling with kids. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
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Map
Islamorada, FL

What's nearby

  • Robbie’s of Islamorada - 1 min drive - 1.4 km
  • Indian Key Historic State Park - 2 min drive - 2.4 km
  • Sunset Drive Beach - 4 min drive - 4.7 km
  • Bud n' Mary's Dive Center - 5 min drive - 6.3 km
  • Anne's Beach - 5 min drive - 6.6 km

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 32 min drive

Restaurants

  • ‪Lorelei Restaurant & Cabana Bar - ‬7 min drive
  • ‪Lazy Days Restaurant - ‬4 min drive
  • ‪Islamorada Fish Company - ‬6 min drive
  • ‪Papa Joe’s Waterfront - ‬3 min drive
  • ‪Bayside Gourmet of Islamorada - ‬8 min drive

Frequently asked questions

Does Booking heavily for 2027 and 2028! - Stunning Oceanfront Estate - Private Pool have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

How much does it cost to stay at Booking heavily for 2027 and 2028! - Stunning Oceanfront Estate - Private Pool?

As of 21 Aug, 2026, prices found for a 1-night stay for 2 adults at Booking heavily for 2027 and 2028! - Stunning Oceanfront Estate - Private Pool on 28 Aug, 2026 start from S$18,187, 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 Booking heavily for 2027 and 2028! - Stunning Oceanfront Estate - Private Pool pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.

How much is parking at Booking heavily for 2027 and 2028! - Stunning Oceanfront Estate - Private Pool?

On-site parking is available at the property.

What time is check-in at Booking heavily for 2027 and 2028! - Stunning Oceanfront Estate - Private Pool?

Check-in begins at 4:00 PM.

What time is check-out at Booking heavily for 2027 and 2028! - Stunning Oceanfront Estate - Private Pool?

Checkout is at 10:00 AM.

Where is Booking heavily for 2027 and 2028! - Stunning Oceanfront Estate - Private Pool located?

Nestled on the beach, this Matecumbe holiday home is within 1 mi (2 km) of Robbie’s of Islamorada and Indian Key Historic State Park. Sunset Drive Beach and Bud n' Mary's Dive Center are also within 3 miles (5 km).

About the host

Hosted by Michele Rosborough

Host profile image
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.

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.

Premier Host

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