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Stunning Oceanfront Estate with Private Pool ~ Beach.

Beach holiday home with water park and outdoor pool

Photo gallery for Stunning Oceanfront Estate with Private Pool ~ Beach.

Overview
Dock to house
Pool deck
Pool
Oceanside deck

Reviews

10 out of 10
Exceptional
6 bedrooms6+ bathroomsSleeps 14436.6 sq m

Popular amenities

  • Parking available
  • Pet-friendly
  • Pool
  • Dryer
  • Air conditioning
  • Washer

Explore the area

View map
Islamorada, FL
  • Place, Robbie’s of Islamorada
    ‪12 min walk‬
  • Place, Bud n' Mary's Dive Center
    ‪5 min drive‬
  • Place, Anne's Beach
    ‪6 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪42 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

Stunning Oceanfront Estate with Private Pool ~ Beach.

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 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 *

This house can book up to two years in advance and is already taking bookings for 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 new 2026 listing.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi

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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

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. The area's natural beauty can be seen at Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park, while MoradaWay Arts & Cultural District and Keys History & Discovery Center are cultural highlights. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Islamorada, FL

What's nearby

  • Robbie’s of Islamorada - 12 min walk - 1.0 km
  • Sunset Drive Beach - 4 min drive - 5.0 km
  • Bud n' Mary's Dive Center - 5 min drive - 6.3 km
  • Anne's Beach - 6 min drive - 7.0 km
  • Florida Keys Brewing Co. - 9 min drive - 9.7 km

Getting around

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

Restaurants

  • ‪Hungry Tarpon Restaurant - ‬10 min walk
  • ‪Lorelei Restaurant & Cabana Bar - ‬7 min drive
  • ‪Lazy Days Restaurant - ‬4 min drive
  • ‪Papa Joe’s Waterfront - ‬3 min drive
  • ‪Islamorada Fish Company - ‬6 min drive

Frequently asked questions

Does Stunning Oceanfront Estate with Private Pool ~ Beach. have a pool?

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

Is Stunning Oceanfront Estate with Private Pool ~ Beach. pet-friendly?

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

What time is check-in at Stunning Oceanfront Estate with Private Pool ~ Beach.?

Check-in begins at 4:00 PM.

What time is check-out at Stunning Oceanfront Estate with Private Pool ~ Beach.?

Checkout is at 10:00 AM.

Where is Stunning Oceanfront Estate with Private Pool ~ Beach. 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).

Reviews

10

Exceptional

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy
Rating 10 - Excellent. 56 out of 57 reviews
Rating 8 - Good. 1 out of 57 reviews
Rating 6 - Okay. 0 out of 57 reviews
Rating 4 - Poor. 0 out of 57 reviews
Rating 2 - Terrible. 0 out of 57 reviews

Reviews

10/10 Excellent

Kim E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

The property is beautiful, with ample space for a large group. We had 14 people, all adults, and everyone was comfortable during our stay. Sue is great to work with, very prompt when assistance was needed.
Stayed 7 nights in May 2025

10/10 Excellent

Stefanie P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vaca

Amazing property!
Stayed 7 nights in Nov 2024

10/10 Excellent

candy r.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beach trip

Beautiful property-plenty of room for 10 adults-easy access to restaurants and shopping
Stayed 7 nights in Aug 2024

10/10 Excellent

Robert B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful vacation

Relaxing in a tropical paradise. Great time spent with family
Stayed 7 nights in Jul 2023

10/10 Excellent

Jodi W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay in the Keys!

We have a large family with wide age range from married kids to kindergarten and everyone had fun! Kyaks and snorkeling were fantastic! Corn hole boards could use a refresh but honestly, standing in the whote sand with the best backdrop you could ever imagine for family fun with the turquoise blue waters of the shallow ocean in the background!
Stayed 7 nights in Jul 2024

10/10 Excellent

William E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome house

We had family and had a Great time fishing, swimming and hired chef Wes for. Meal one night
Stayed 7 nights in Oct 2023

10/10 Excellent

Karen B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Vacation

Beautiful property. Couldn’t have asked for a more perfect vacation. Property manager was such a delight to work with. Would give 10 stars!!
Stayed 7 nights in Sep 2022

10/10 Excellent

Darla D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Anniversary Trip

This place is awesome! 5 couples, plenty of space. We spent most of our time on the back porch, the dock and around the pool. The only thing that could have made our stay better was the weather. Sue was amazing and very attentive. Would definitely stay there again!
Stayed 7 nights in May 2021

10/10 Excellent

Donna N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Fun

Great place for our extended families. Watching the 2 toddlers, enjoying the beach . Had lots of family meals una well stocked kitchen . Great propert manager .
Stayed 7 nights in Nov 2021

10/10 Excellent

Susan N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

good choice

well maintained property.
Stayed 7 nights in Nov 2023

10/10 Excellent

Paul C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic.

This is a gorgeous property and a beautiful house for big groups. Sue was an awesome host and very responsive! Thanks for a wonderful vacation with grown kids, significant others, and a new grandbaby.
Stayed 7 nights in Dec 2020

10/10 Excellent

Leisa M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful week

Beautiful property with all the amenities needed for our entire family from the infants to the Grand Parents. I cannot say enough wonderful things. 100% recommended.
Stayed 7 nights in Feb 2023

10/10 Excellent

Lucy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome vacation home

Sue is terrific with everything. Awesome views from home. Grandkids loved kyacking and swimming. Sunsets beautiful. Home is beautiful with every amenity required. I give a rating of 10!
Stayed 7 nights in Jun 2022

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise in the Keys

This villa is exactly what everybody needed for a relaxing getaway. Lots of space for everybody to spread out. Plenty of common gathering areas for our group to enjoy each other's company. Tons of refrigerator space for food and drinks. Beautiful views. Close to restaurants. Super clean. We would definitely come back.
Stayed 7 nights in Feb 2023

10/10 Excellent

Teresa W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous!

Just right for our annual family retreat! (Six adults in their 30s, two adults in their 60s, and 5 y.o., 3 y.o., 2 y.o. children plus infant.) Great sleeping arrangements, excellent gathering spaces, well-equipped kitchen and laundry room, plus lovely sand for playing, wonderful little pool, fishing pier, hammock, kayaks and bikes. Something for everyone and very private!
Stayed 7 nights in Jan 2023

10/10 Excellent

Brian S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

House is as advertised

The house is super well stocked with everything you could need which is a breath of fresh air. Property management was responsive and gave great tips on things to do. The house had bikes, fishing gear, all kinds of cooking spices, oils, coffee, games, puzzles, etc. The pool was clean. The only negative about the area is the humidity but that's to be expected in July. The magic show at Lorelei was awesome and I highly recommend it. Windley park was a nice park with an easy couple of hiking trails.
Stayed 7 nights in Jul 2024

10/10 Excellent

Loretta M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A MAGICAL place!!

Just to begin, the property manager was the best we have ever encountered! Sue was always available and communication with her was easy. Sue made sure we knew about the many amenities and was professional, informative and friendly! If there were 15 stars I would give her 15! The house was spacious and comfortable. Our family included adults, children and an infant and - though we were outside on the beach, in the pool, and fishing from the dock most of the time - there was plenty of private space for reading and relaxing. “Last Too Resort” was the perfect home for our family and Sue was the very best!
Stayed 7 nights in Jul 2024

10/10 Excellent

Kelly S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect House for Large Group

Our recent stay (10/5 - 10/12/24) involved five couples ages 50+. We each had our own room with a king size bed and en suite bathroom. The gated property is private and the grounds beautiful. The house is a little more weathered than the pictures portray, but still in good shape. The front door was not locking, which was a little concerning, but our handy men were able to fix it. The inside decor of each room is gorgeous and very comfortable. The house is INCREDIBLY stocked with everything you want and/or need. Great bar area. We were blown away by how well organized the kitchen was and how many spices there were! The outdoor bbq area, just off the kitchen, is fabulous. Everyone was able to fit around the dining table for dinner. The outdoor porch areas are lovely and all areas of the house, with the exception of one room, have expansive views of the ocean. The coach house off the pool area was perfection as well with a full kitchen and fridge that was helpful when hanging out at the pool all day. The pool is medium size with some built in seating areas in the corners. That made it easy to converse while relaxing. We did have to do a bit of skimming each day to clean out leaves and such. The pool man came by twice to vacuum. There are kayaks, paddle boards, and fishing equipment available on the side of the house. The only downside were the sand fleas/"noseeums". All of us got pretty chewed up. Very itchy. Despite that, we all would HIGHLY recommend this property.
Stayed 7 nights in Oct 2024

10/10 Excellent

Debra H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a wonderful home to gather in! It was clean, big enough for 3 families, the pool was clean, they even has paddle boards, bikes and kayaks you could use. You could fish off the dock, which our 5 year old couldn’t get enough of, fully stocked kitchen with any utensil and pan you would ever need. Really great place to stay. Oh, and the host was superb, and question we had she answered in minutes!
Stayed 7 nights in Aug 2025

10/10 Excellent

Valerie P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

We thought it was a perfect place for our family. We had days of doing things off property as well as staying there and playing. We saw great wildlife. Rays, turtles, a manatee and her baby. We really enjoyed our time there.
Stayed 7 nights in Feb 2025

10/10 Excellent

Kim L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome!

Wonderful family vacation at a beautiful home. We had such a great time. Sue was super accessible and did an amazing job. Would recommend this home!
Stayed 7 nights in Jan 2025

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Familymoon

It was a fabulous trip!!! We were celebrating the marriages of two couples who decided the family could tag along. The house is beautiful and so well organized! We had lots of room and many activities to do right on the property! Our host was so helpful and responsive! I can’t say enough good things about the whole experience! Would most definitely stay at the Last Resort Too again! I have already recommended to a friend with large family.
Stayed 7 nights in Aug 2024

10/10 Excellent

Andy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fournie family

Perfect for our family
Stayed 7 nights in Jun 2024

10/10 Excellent

milton M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Traveling with friends

The property was well equipped..host was available when needed
Stayed 7 nights in Jun 2024

10/10 Excellent

debra s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beyond expectations

The property exceeded our expectations and Sue was absolutely lovely.
Stayed 7 nights in Mar 2024

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.

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