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Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool

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Overview
Dock to house
Pool deck
Pool
Oceanside deck

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
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)
    ‪41 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

Next available August 15th, 2026 - 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 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.

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Exterior
Southern Diversion Estate Islamorada
Matecumbe
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
9.8 out of 10, Exceptional, (85 reviews)
Southern Diversion Estate Islamorada

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

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. 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.
View more Holiday homes in IslamoradaOpens in a new window
Map
Islamorada, FL

What's nearby

  • Robbie’s of Islamorada - 1 min drive - 1.0 km
  • Indian Key Historic State Park - 2 min drive - 2.0 km
  • Sunset Drive Beach - 4 min drive - 4.7 km
  • Bud n' Mary's Dive Center - 5 min drive - 6.0 km
  • Anne's Beach - 5 min drive - 6.6 km

Getting around

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

Restaurants

  • ‪Hungry Tarpon Restaurant - ‬10 min walk
  • ‪Lazy Days Restaurant - ‬4 min drive
  • ‪Lorelei Restaurant & Cabana Bar - ‬7 min drive
  • ‪Papa Joe’s Waterfront - ‬3 min drive
  • ‪Wendy's - ‬7 min drive

Frequently asked questions

Does Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool have a pool?

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

Is Next available August 15th, 2026 - 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 Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool?

On-site parking is available at the property.

What time is check-in at Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool?

Check-in begins at 4:00 PM.

What time is check-out at Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool?

Checkout is at 10:00 AM.

Where is Next available August 15th, 2026 - 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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 58 out of 59 reviews
Rating 8 - Good. 1 out of 59 reviews
Rating 6 - Okay. 0 out of 59 reviews
Rating 4 - Poor. 0 out of 59 reviews
Rating 2 - Terrible. 0 out of 59 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jenn K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic stay. Perfect location. RoomFor everyone and the beds were super comfy.
Stayed 7 nights in Jan 2026
Verified

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
Response from VrboOwner on 13 Aug, 2025
Thank so much for your review Debra! What a great trip for your group:) We are glad you enjoyed the Last Resort Too. You were such a pleasure to assist in planning your trip. Hope to see you again soon:)
Verified

10/10 Excellent

Stefanie P.

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

Family Vaca

Amazing property!
Stayed 7 nights in Nov 2024
Response from VrboOwner on 27 Nov, 2024
Thank you Stefanie! I'm so glad your family enjoyed the Last Resort Too! We hope to see you again in Islamorada!
Verified

10/10 Excellent

Michaelene Z.

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

Excellent, clean property. Owner was very helpful, Home is just gorgeous.

Love this property and renting was super easy!
Stayed 7 nights in Mar 2023
Response from VrboOwner on 19 Jul, 2023
Thank you for taking the time to leave a review. I am happy that you enjoyed your stay at the Last Resort Too and Islamorada!
Verified

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
Response from VrboOwner on 4 Jun, 2025
Thank you Kim for your kind review:) We are happy that we had the opportunity to host your family and friend vacation! We hope to see you again in Islamorada!
Verified

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
Response from VrboOwner on 2 Mar, 2025
Thank you Valerie for your sweet review:) I enjoy hearing about your families experiences while at Last Resort Too! How special to se a manatee momma and her baby. That is such a treat! Thank you for allowing us to host your stay.
Verified

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
Response from VrboOwner on 24 Aug, 2024
Thanks Candy... you were fabulous to work with! I hope we meet up again in Islamorada!
Verified

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
Response from VrboOwner on 13 Aug, 2023
Thank you chuck for your nice review. I am glad that you enjoyed your week in the Keys with your family and friends:)
Verified

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
Response from VrboOwner on 10 Feb, 2025
Thank you Kim for your nice review. I'm so glad that your family enjoyed their week at The Last Resort Too! We hope to see you again:)
Verified

8/10 Good

sarah C.

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

Beautiful views, peaceful, enough room for all.

Wonderful week with the family. Paddle board with the sunrise and lounge by the pool during the day. Close access to restaurants and water excursions.
Stayed 7 nights in Aug 2022
Response from VrboOwner on 19 Jul, 2023
Thank you Sarah for your review! I hope you and your family will come back to visit us again at The Last Resort Too:)
Verified

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
Verified

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
Response from VrboOwner on 16 Jun, 2024
Thank you for taking the time to leave our home a review. Very glad that you and your friends had a nice week at the Last Resort Too!
Verified

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
Response from VrboOwner on 10 Apr, 2024
Thank you Deb for your review! It was a pleasure meeting you and your family. Hope to see you again next year:)
Verified

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
Response from VrboOwner on 7 Nov, 2023
Thank you for your nice review. I am glad that you enjoyed a great trip with your family at the Last Resort Too! Islamorada has so much to offer to families of all ages:)
Verified

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
Response from VrboOwner on 4 Aug, 2024
Thanks Jodi for your review. I am so happy that you and your family enjoyed a fun week together at The Last Resort Too. It really is the perfect multi generational home!
Verified

10/10 Excellent

Ray D.

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

Great place just need kayaks and softer sand

Unbelievable property beautiful landscaping everything was great just need a few things softer sand in rear property and some kayaks
Stayed 9 nights in Jan 2020
Response from VrboOwner on 19 Jul, 2023
Thank you Ray... I'm so glad that you enjoyed Southern Comfort. Our beach sand is unlike other areas... The Keys is very unique:) I agree kayaks would be lovely at the property.
Verified

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
Response from VrboOwner on 19 Jul, 2023
Thank you Karen for your awesome review! I hope you and your family will come back and visit us again at The Last Resort Too:)
Verified

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
Response from VrboOwner on 19 Jul, 2023
Thank you Darla... I tried to order better weather but Mother Nature must have been on vacation:) I hope to see you again:) Thank you for staying with us at the Last Resort Too!
Verified

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
Response from VrboOwner on 19 Jul, 2023
Thank you Donna! What a gorgeous week with the grand kids:) You were able to stock up on Vitamin D! We appreciate you visiting us here in Islamorada.
Verified

10/10 Excellent

Linda K.

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

Beautiful property

From our first drive onto the property we enjoyed our stay! We made plenty of wonderful memories each day as we enjoyed everything the property had to offer! If we had an issue Sue was available to answer questions and provide a solution! We loved being in Islamorada! Hope to get back again!
Stayed 7 nights in May 2021
Response from VrboOwner on 19 Jul, 2023
Thank you Linda for staying with us at the Last Resort Too! So nice to hear that you enjoyed your stay in Islamorada:)
Verified

10/10 Excellent

Kay B.

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

This place is amazing!

The house is absolutely beautiful with views from every room. The dock, pool, beach area and porches provide enough space that a large group can spread out. They have everything there you could need, kayaks, kids kayaks, corn hole, and fishing poles. It's close and convenient to everything in Islamorada but with such a beautiful place we didn't want to leave.
Stayed 7 nights in Apr 2023
Response from VrboOwner on 19 Jul, 2023
Thank you Kay for your beautiful review! The Last Resort Too is really a fun and charming oceanfront family retreat. I am so glad that you and your family enjoyed your trip to Islamorada!
Verified

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
Response from VrboOwner on 19 Jul, 2023
Thank you Paul for staying with us at Southern Comfort! I'm so happy that you and your family enjoyed your visit .Beautiful weather for your New Year's week:)
Verified

10/10 Excellent

Andrea M.

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

Plenty of room!

We had 2 families (10 people) and we had plenty of room for everyone without feeling the least bit crowded. The pool was awesome and the sunset and sunrises were incredible. Not a beach like we are used to to, but you’re able to easily get in the ocean. The house was super comforted and well equipped. We would definitely stay here again!
Stayed 7 nights in Dec 2020
Response from VrboOwner on 19 Jul, 2023
Thank you Andrea I appreciate you sharing your review of Southern Comfort. I'm glad you and your family enjoyed your visit to the Keys!
Verified

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
Response from VrboOwner on 19 Jul, 2023
Thank you Leisa for your review. What a memorable vacation with 3 generations! Come back and visit us again in Islamorada!
Verified

10/10 Excellent

Susan N.

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

good choice

well maintained property.
Stayed 7 nights in Nov 2023
Response from VrboOwner on 5 Dec, 2023
Thank you for your review. I am glad you enjoyed your stay at the Last Resort Too! We hope to see you again in Islamorada:)

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

They consistently provide great experiences for their guests
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