Southern Diversion Estate Islamorada

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Entire home

Overview
Amenities
Policies
Location
Host

Exceptional

5 bedrooms3+ bathroomsSleeps 16511 sq m

Popular amenities

Parking available
Dryer
Air conditioning
Washer
Barbecue grill

Explore the area

Islamorada, FL

History of Diving Museum
‪9 min walk‬
Florida Keys Brewing Co.
‪3 min drive‬
Theater of the Sea
‪3 min drive‬
Marathon, FL (MTH-Florida Keys Marathon)
‪40 min drive‬

Rooms & beds

5 bedrooms (sleeps 16)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

2 Single Beds and 1 Single Bunk Bed

Bedroom 5

2 Single Bunk Beds

3 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only · Jetted bathtub

Bathroom 2

Toilet

Bathroom 3

Bathtub · Toilet · Shower only

Bathroom 4

Toilet · Shower only

Spaces

Deck or patio

Porch or lanai

Kitchen

Office

Balcony

Outdoor play area

Garden

Dining area

About this property

Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the major restaurants and shopping. This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, tiki hut on private beach, heated pool and wireless remote Internet. Southern Diversion pool and patio area has just been completely renovated with marble decks.

Islamorada is located one hour and 1/2 south of South Beach and two hours north of Key West. This spectacular oceanfront estate features 5 bedrooms, 3.5 baths. Bedroom One: king bed, Bedroom Two: 1King bed , Bedroom Three: 1 King bed, Bedroom Four: 1 bunk-bed with a pull-out trundle and 2 twin beds, Bedroom 5: 2 sets of bunk beds with trundle. Bottom bunk on one bed is a double. Brand new flat screens in every room.We provide a full time property manager available 24/7 for anything our guests may need. Southern Diversion offers the perfect escape and tropical dream vacation. Occupancy is 2 adults per room. Children 6 and older are considered adults. Under 6 not included in occupancy count.

Islamorada The Sport Fishing Capital of the World hosts an array of activities from relaxing on our private beach to world class scuba diving. From our private beach you can go catch fresh Florida lobster, Go shelling, Reef snorkeling off Cheeca Rock Reef, See live coral reefs and catch Bonefish. Southern Diversion is located directly in the Village of Islamorada (Mile Marker 82) which means you are within 5 minutes of the best cuisine Islamorada has to offer. Robbie's of Islamorada (5 min car ride) offers many different marine activities including boat rentals, jet skiing, kayak's and a delicious restaurant. Don't forget to visit Scarface in the Tarpon Feeding area. Also at Robbie's they will cook your fresh catch at the Hungry Tarpon Restaurant. If you are in the mood for a nice stroll, Bentleys Restaurant is right outside our gate or you can walk to Morada Bay where you can enjoy a relaxed beach atmosphere.
Feel free to visit other Southern Diversion Properties in The Florida Keys
homeaway 7396601
homeaway 3577977
Keywords: Estate Home
License No. VR-087

Property manager

Terri Melilli

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Amenities

Pool

Kitchen

Washer

Dryer

Free WiFi

Air conditioning

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Ocean view
Pool
Kitchen
Washer

House Rules

Check in after 4:00 PM

Minimum age to rent: 23

Check out before 10:30 AM

Children

Children allowed: ages 0–17

Events

Events allowed: family gatherings, birthday parties, weddings

Pets

No pets allowed

Smoking

Smoking is not permitted

Partys or Weddings 20 to 30 people require a 1500.00 event fee Over 30 is 4000.00

We have a 90 day cancellation policy . This is listed in our contract.

Any weddings over 30 guests require a security guard at gate of property to be paid by guest

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

Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 73

Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip

Host has not indicated whether there is a smoke detector on the property

About the area

Islamorada

Located on the beach, this holiday home is in Matecumbe, a neighbourhood in Islamorada. History of Diving Museum and Keys History & Discovery Center are cultural highlights, and some of the area's landmarks include Hurricane Monument and Indian Key Historic State Park. Jet skiing, kayaking and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.

View more Holiday homes in Islamorada

Islamorada, FL

What's nearby

History of Diving Museum - 9 min walk - 0.8 km
Islamorada Brewery & Distillery - 12 min walk - 1.1 km
Florida Keys Brewing Co. - 3 min drive - 2.5 km
Theater of the Sea - 3 min drive - 3.0 km
Bud n' Mary's Dive Center - 5 min drive - 5.1 km

Getting around

Marathon, FL (MTH-Florida Keys Marathon) - 40 min drive

Restaurants

‪Lorelei Restaurant & Cabana Bar - ‬2 min drive
‪Wahoo's Bar & Grill - ‬17 min walk
‪Florida Keys Brewing Co. - ‬3 min drive
‪Whale Harbor Restaurant Marina - ‬17 min walk
‪Trading Post Grocery Store - ‬2 min drive

Frequently asked questions

Does Southern Diversion Estate Islamorada have a pool?

Yes, this property has a pool.

Is Southern Diversion Estate Islamorada pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Southern Diversion Estate Islamorada ?

Check-in begins at 4:00 PM.

What time is check-out at Southern Diversion Estate Islamorada ?

Checkout is at 10:30 AM.

Where is Southern Diversion Estate Islamorada located?

This family-friendly Islamorada holiday home is located on the beach, within a 15-minute walk of History of Diving Museum and Islamorada Brewery & Distillery. Keys History & Discovery Center and Matecumbe United Methodist Church are also within 1 mile (2 km).

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

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9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

6/10 Okay

Herb S.

26 Mar 2025

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

Disliked: Communication

Incredibly beautiful spot...BUT....

Watching a sunrise every morning from a private beach is amazing. It's well-situated, comfortable, clean, and very dated. There are literally plastic ties holding handrail pickets in place. We overlooked these as the place really was comfortable.All went well the first several days, until on Friday night (8-ish PM) as my friend and I were on the dock enjoying a drink (wives inside), and a stranger walked up behind us and started talking about needing to service the air conditioner. My friend (a state trooper) sensed something out of order: Friday night after dark, a shadowy figure approaches us from behind, dressed like someone just off a fishing boat, in a beat-up truck. We asked him to leave, as we had not heard from the property manager about any service. The whole affair was quite sketchy.We packed up the next morning, a day early. In speaking with the property manager the next morning, he told me this guy called him at 9 PM the previous night and told the manager we made him leave.The manager didn't think it was important, and didn't bother to call at all to vouch for the situation. It wasn't until I called him the nearly 24 hours later that he told me the service tech was legit.Communication with the owner wasn't great. I was hoping to use the boat lift -- and mentioned in my booking request, but got no answer on that. When I asked again, I got a curt answer: "Lift not available. Not functioning currently."I wouldn't rent here again.

Stayed 8 nights in Mar 2025

10/10 Excellent

David C.

23 Mar 2025

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

Family Vacation

Beautiful setting in Islamorada! Outdoor area is well maintained with a beautiful pool and beach area. The house is somewhat dated but very functional for a beach vacation. There are several great restaurants nearby. The property manager is very responsive. Would rent again.

Stayed 7 nights in Feb 2025

8/10 Good

Jean R.

2 Mar 2025

Liked: Cleanliness, check-in, communication, location

Stayed 7 nights in Feb 2025

8/10 Good

James J.

5 Feb 2025

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

Week at a nice quiet place

Was there before and would go back again

Stayed 7 nights in Jan 2025

6/10 Okay

John C.

30 Jan 2025

Liked: Check-in, communication, location

Disliked: Cleanliness

OK, but….

This property has a beautiful pool, grounds, and ocean front view. However, the house itself needs updating and cleaning.

Stayed 7 nights in Jan 2025

10/10 Excellent

Lisa C.

11 Jan 2025

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

Family gathering

This was an opportunity for our family to gather after an 8 month separation due to one of us being out of the country. This home offered a beautiful retreat to do just that. It is a little slice of paradise! It actually isn’t little. There were plenty of beds for everyone, 2 acres to run around throwing the football, a beautiful private beach (very unusual in this part of Florida), a heated pool overlooking the ocean, a basketball goal,the opportunity to paddle board and kayak, and more. We also enjoyed just lounging around. There were plenty of Adirondack chairs, a hammock under two palm trees, and several chaise lounges as well. We played games at the indoor dining table at night and we ate outside at the tables on the upper porch. There were several spots to choose from for dining. We loved this home and property and would definitely recommend it highly if visiting the Keys! The host was great as well and had many suggestions for restaurants and for things to do in the area. Great trip!

Stayed 7 nights in Jan 2025

10/10 Excellent

Cathy C.

2 Dec 2024

Liked: Check-in, location, listing accuracy

Stayed 7 nights in Nov 2024

10/10 Excellent

S B.

14 Aug 2024

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

Stayed 7 nights in Jul 2024

8/10 Good

amy w.

11 Aug 2024

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

Nice house but boat use was challenging during low tide

The house was comfortable. The manager was exceptionally responsive. The owner was easy to reach. The one constant challenge was using our boat (27' Grady White) at low tide. The water depth at low tide is so low that we had to push our boat out 200+ yards. During many of these pushes the boat ran aground and required three men to push and pull with ropes.

Stayed 7 nights in Aug 2024

10/10 Excellent

Tim W.

11 Aug 2024

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

Stayed 7 nights in Jun 2024

10/10 Excellent

Michael C.

31 July 2024

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

Stayed 7 nights in May 2024

10/10 Excellent

Teresa J.

9 June 2024

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

Beautiful House and Great Location

Southern Diversion is a beautiful, comfortable Keys house, directly on the Atlantic ocean. The view from living spaces and most bedrooms is stunning! The 2 acre property is extra special for the Keys. The layout of the house worked well for our family with two primary bedrooms with en suites and bunk rooms for the younger children. The outside porch was a fun addition to the living space, and the pool deck with lots of shade was wonderful for kids and adults. The kitchen was outstanding with 6 bar stools for the large counter and all the dishes and extras needed. The second refrigerator in utility room was helpful for large family! The dock was an excellent amenity for our boat. And the location was excellent with all the nearby shops, Publix and restaurants. We rented a golf cart to get around. We usually stay further south in less populated areas, but Islamorada with its many conveniences and with the nearby snorkeling reefs and the sandbar makes it great for all the family. The host was very helpful with information before the trip. Hope to return in the future.

Stayed 7 nights in Jun 2024

10/10 Excellent

Shawn S.

6 May 2024

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

Perfect

It was just as advertised

Stayed 7 nights in Apr 2024

10/10 Excellent

Jan R., Pleasanton

17 Mar 2024

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

Family Time

We had a wonderful family stay. Jon, the property manager was very helpful during check in! We loved the location, so close to grocery shopping and restaurants. We spent a lot of our time at the house , enjoying the gorgeous outdoor areas. The water was beautiful! We were six adults and six younger children. It was really nice to have so much room for everyone! The beds and linens were very comfortable, always important to us! We had a great time and will be visiting again!

Stayed 7 nights in Mar 2024

10/10 Excellent

Shaunna M.

25 Feb 2024

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

Beautiful

This place was hands down a Cadillac in a land of Buicks. The Southern Diversion has everything we needed. The beach was stunning and the water was crystal clear. Sea life was amazing. We saw a nurse shark, sting rays, box fish, barracudas, needle fish, and more right off our dock. The host was quick to respond to any questions we had. Our family will definitely be staying at this place again.

Stayed 7 nights in Feb 2024

10/10 Excellent

Andy D.

25 Oct 2023

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

The keys are something different

We absolutely loved our stay in Islamorada. We have visited the keys a few times and never want to leave. This property was absolutely incredible. The pictures really don’t do the view justice of how beautiful this view is. Kids saw lots of fish off the dock every day and loved it. The property was maintained beautifully and the property manager helped in anyway we needed. We be booking again and cannot wait to go back. If you have considered the keys, do it! You won’t regret it and this property is one a kind to stay at. Thank you guys again!

Stayed 8 nights in Oct 2023

10/10 Excellent

Amy F.

31 May 2023

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

Perfect setting for our family

The property was everything that was listed on VRBO. The pool area and beach is where we stayed most of the time. It was very nice not to have to haul everything for the toddlers to the beach. The children could nap and the adults were still able to be out by the pool and beach. It was nice to have shaded areas for those not wanting to be in the sun. The only drawback to the beach was the seaweed. We were not able to get in the water at the house. The seaweed was thick and smelly. However the pool was perfect for us. We rented 2 golf carts for our family to use to get around town while there. We were very close to shops, grocery store and restaurants. We did not have to drive out except to boat rental companies. We would definitely recommend staying at this property. Our last day there, we had our own private dolphin show. 2 dolphins swam around and entertained the children by showing off. They were back and forth under the doc coming up to the surface as to say hello to the children. It was very entertaining.

Stayed 7 nights in May 2023

10/10 Excellent

Angela A.

28 Mar 2023

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

Islamorada

The property was very nice and clean. Great location. We enjoyed our stay.

Stayed 7 nights in Mar 2023

10/10 Excellent

Kay L.

18 Mar 2023

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

Paradise in the Keys

We have stayed at many VRBO properties but this one was the best! From waking up to a beautiful sunrise and spending the entire day by the pool and beach! My family, which included 3 grandchildren were in paradise! Joe the property manager was so helpful, with all my questions. The location of the home is right in the middle of the key and close to everything. Thank you for sharing your home with us!

Stayed 7 nights in Mar 2023

10/10 Excellent

Erin M.

14 Feb 2023

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

Fabulous

Our group of kids, parents, and grandparents had an incredible time at this property. Terri and Joe were responsive and kind and helped with all our needs. The house was spacious, had a well stocked kitchen, lots of towels, and most importantly an absolutely beautiful location. We hardly left the pool and beach. Saw dolphins on our last day. Would stay again!

Stayed 7 nights in Feb 2023

10/10 Excellent

Matthew B.

3 Jan 2023

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

Very nice

Excellent

Stayed 7 nights in Dec 2022

10/10 Excellent

Susan K.

25 Oct 2022

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

Perfect Family getaway

This location is perfect for families with small children. The pool sits in front of the house, the view of the ocean from here is outstanding. Beware, the air conditioner can not be turned below 72 or the system freezes up.

Stayed 6 nights in Oct 2022

10/10 Excellent

Ruby M., Mount Pleasant, SC

24 July 2022

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

very nice

beautiful location

Stayed 7 nights in Jul 2022

10/10 Excellent

Evan D.

5 June 2022

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

Wonderful escape

From the moment we arrived to the moment we left, the entire group (ages 5-46) had a great time. The house is gorgeous, very well-appointed, and very very near any shops we needed for our stay. Town is overflowing with great eateries, and many of them are within a two or three minute drive of the house. The dock out back and the pool and shaded seating area beneath were in almost constant use. We rented kayaks and paddle boards (supplied by Joe, who is an incredible resource) and spent time paddling and seeing several varieties of fish, even one small hammerhead! The only negative things I will mention are 1. the accumulation of seaweed, but this is a fact of life throughout the Keys, and did almost nothing to dampen our enthusiasm. 2. Some of the houses along the street to the property could use a little TLC, but this again did nothing to effect our stay, I only mention it as someone else coming to the property should not be put off when they see it, as it’s invisible once within the gate and in no way bothered us the entire stay. We had a great time and I wouldn’t hesitate to come back. Wonderful trip, wonderful location.

Stayed 7 nights in May 2022

10/10 Excellent

Sondra K.

5 May 2022

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

Terrific home great for groups

We had a small retreat at this property and the owner and manager were extremely easy to work with and went above any beyond to make our stay terrific. We had a few minor maintenance issues that were handled quickly and overall the house and property were terrific!

Stayed 7 nights in Feb 2022

About the host

Hosted by Terri Melilli

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Southern Diversion Estate Islamorada

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Popular amenities

Explore the area

Rooms & beds

5 bedrooms (sleeps 16)

Bedroom 1

Bedroom 2

Bedroom 3

Bedroom 4

Bedroom 5

3 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Spaces

About this property