Entire home

Southwind Islamorada: Beachfront Estate with Pool, Spa & Fishing Pier

Photo gallery for Southwind Islamorada: Beachfront Estate with Pool, Spa & Fishing Pier

Relaxing beach chairs
A gated entrance with a sign reading 'SOUTHWIND' and a house with a white facade and multiple windows.
A beachfront property with a large house, tennis courts, and palm trees.
A two-story house with a pool, surrounded by palm trees and a well-maintained lawn.
Exterior

Reviews

10 out of 10, Loved by Guests
Top 1% of guest reviews in this area

Highlights

  • Beach, waves and sand
    Guests enjoy the stunning beach views at this property.
  • On the beach
    A rare beachfront property in the area - enjoy direct access to the beach and sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • On beach
  • Balcony
  • Hot tub on site
  • Private pool
  • Dog-friendly
  • On-site fitness centre

Explore the area

View in a map
Islamorada, FL
  • Place, Sunset Drive Beach
    ‪2 min drive‬
  • Place, Robbie’s of Islamorada
    ‪3 min drive‬
  • Place, Anne's Beach
    ‪3 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪36 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

1 - Oceanfront Primary King Suite - Level 3 - Ensuite Bath

1 King Bed

2 - Oceanfront Queen Suite - Level 3 - Ensuite Bathroom

1 Queen Bed

3 - Garden View Twin Suite - Level 3 - with Ensuite

1 Double Sofa Bed and 2 Single Beds

4 -Garden View Twin & Bunk Suite - Main Level -Ensuite

1 Single Bunk Bed and 2 Single Beds

5 - Garden View King Suite - Main Level - Ensuite bathroom

1 King Bed

6 bathrooms, 1 half bathroom

1 - Primary Suite Bathroom

Soap · Towels provided · Bathtub · Toilet · Shower only · Shampoo · Hair dryer

2 - Top Level Oceanfront Ensuite Bath

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

3 - Top Level Guest Suite Garden View Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

4 - Main Level Garden View Suit (bunk) Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

5 - Main Level Garden View Suite Bathroom

Soap · Toilet · Shower only

6 - Main Level Powder Room

Soap · Towels provided · Toilet · Shampoo · Hair dryer

7 - Pool Bathroom - Ground level

Soap · Towels provided · Bathtub · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Number of living rooms
Outdoor play area
Garden
Dining area

Add dates for prices

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About the area

Islamorada

Located on the beach, this holiday home is in Matecumbe, a neighbourhood in Islamorada. Keys History & Discovery Center and History of Diving Museum are cultural highlights, and some of the area's landmarks include Indian Key Historic State Park and Hurricane Monument. Consider Lorelei Restaurant & Cabana Bar for a night out or MoradaWay Arts & Cultural District if you're travelling with kids. Discover the area's water adventures with jet skiing, kayaking and scuba diving nearby, or enjoy the great outdoors with ecotours.
View more Holiday homes in IslamoradaOpens in a new window
Map
Islamorada, FL

What's nearby

  • Sunset Drive Beach - 2 min drive - 2.7 km
  • Robbie’s of Islamorada - 3 min drive - 3.4 km
  • Anne's Beach - 3 min drive - 4.6 km
  • Indian Key Historic State Park - 4 min drive - 4.4 km
  • Bud n' Mary's Dive Center - 6 min drive - 8.3 km

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 30 min drive

Restaurants

  • ‪Hungry Tarpon Restaurant - ‬2 min drive
  • ‪Habanos Oceanfront Dining - ‬3 min drive
  • ‪Lorelei Restaurant & Cabana Bar - ‬9 min drive
  • ‪Lazy Days Restaurant - ‬5 min drive
  • ‪Papa Joe’s Waterfront - ‬5 min drive

Frequently asked questions

Does Southwind Islamorada: Beachfront Estate with Pool, Spa & Fishing Pier have a pool?

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

How much does it cost to stay at Southwind Islamorada: Beachfront Estate with Pool, Spa & Fishing Pier?

As of 11 Nov 2026, prices found for a 1-night stay for 2 adults at Southwind Islamorada: Beachfront Estate with Pool, Spa & Fishing Pier on 16 Aug 2027 start from £15,933, 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 Southwind Islamorada: Beachfront Estate with Pool, Spa & Fishing Pier pet-friendly?

Yes, this property allows dogs (limit 1 total).

How much is parking at Southwind Islamorada: Beachfront Estate with Pool, Spa & Fishing Pier?

On-site parking is available at the property.

What time is check-in at Southwind Islamorada: Beachfront Estate with Pool, Spa & Fishing Pier?

Check-in begins at 4:00 PM.

What time is check-out at Southwind Islamorada: Beachfront Estate with Pool, Spa & Fishing Pier?

Checkout is at 10:00 AM.

Where is Southwind Islamorada: Beachfront Estate with Pool, Spa & Fishing Pier located?

Nestled on the beach, this Matecumbe holiday home is within 3 mi (5 km) of Sunset Drive Beach, Anne's Beach and Robbie’s of Islamorada. Indian Key Historic State Park is 2 mi (3.2 km) away.

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. 77 out of 81 reviews
Rating 8 - Good. 4 out of 81 reviews
Rating 6 - Okay. 0 out of 81 reviews
Rating 4 - Poor. 0 out of 81 reviews
Rating 2 - Terrible. 0 out of 81 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic house! Loved all the decor and the bedding was amazing!
Stayed 7 nights in Jul 2026
Response from VrboOwner on 30 Jul 2026
Thank you, Jamie! We hope to see you and your family again next year.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cari is the most amazing host we’ve ever had on VRBO. She goes over and above in order to assist and accommodate any requests. She provided wonderful recommendations during our stay that completely enhanced our experience. The home is so well appointed down to the finest details we didn’t even think about wanting! So much fun entertainment at our fingertips. I highly recommend Southwinds! Cari, we’ll be back!
Stayed 7 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Pool / spa was fantastic. Great views, felt private. House was better than the pictures. We really had an enjoyable family week.
Stayed 7 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Incredible home, perfect location, and a true luxury Florida Keys experience! The ocean views from every window are even better than you would find at a five-star resort. The linens, furnishings, and every detail throughout the home are truly high-end and absolutely beautiful. Pickleball and golf right in the front yard were enjoyed by everyone! Hands down, the best rental in the Florida Keys. We are already looking to are stay again next summer!
Stayed 7 nights in Jun 2026
Response from VrboOwner on 13 Jul 2026
Thank you for your review, Rebecca! We are so pleased that you enjoyed your stay and hope that you will join us again next year. You were wonderful and extremely respectful guests. Enjoy the rest of your summer!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing trip! Amazing location. It was a wonderful week and we would stay there again in an instant. It hit all the right notes, thank you!
Stayed 7 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property and property management.
Stayed 7 nights in Nov 2025
Verified review

10/10 Excellent

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

Great location and great house

House is perfect for a family vacation. Amenities are fantastic.
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great time ! Thank you
Stayed 7 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property equipped with everything we needed. A nice, peaceful week enjoyed by all!
Sunrise at Southwind.
Stayed 7 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was spectacular. Very private, with stunning views. Michael and Mike were very easy to work with and responsive, loved the in-person checkin to ensure we got settled okay. Great fishing on the dock!
Stayed 7 nights in Mar 2026
Verified review

10/10 Excellent

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

Wonderful family stay at Southwind

Beautiful and spacious home on the beach with all the amenities needed for multigenerational family vacation fun.
Stayed 10 nights in Feb 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is great especially with a large group like we had - lots of activities, great beach and pet friendly. Michael was responsive and easy to work with if we had questions.
Stayed 7 nights in Dec 2025
Verified review

10/10 Excellent

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

Best Property in Islamorada

Truly enjoyed another stay at this property. Very private , spacious and clean. It’s truly the best property in Islamorada for an authentic Florida Keys getaway.
Stayed 7 nights in Feb 2025
Response from VrboOwner on 10 Mar 2025
Thank you so much.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Michael was very friendly and helpful. Well maintained home with a beautiful view
Stayed 7 nights in Dec 2025
Verified review

10/10 Excellent

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

Gorgeous property!

Beautiful ocean views, lovely outdoor eating area, fabulous pool and hot tub overlooking the beach, well-stocked kitchen. We enjoyed every minute of our stay here!
Stayed 7 nights in May 2021
Verified review

10/10 Excellent

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

Beautiful home

This home was perfect for our fun family vacation!
Stayed 7 nights in Jan 2022
Verified review

10/10 Excellent

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

Everything was excellent!

The view is amazing!
Stayed 7 nights in Mar 2025
Verified review

10/10 Excellent

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

Great home

Our family had a wonderful stay at this property. Everything was well maintained, and we enjoyed using all the amenities offered. We are looking forward to another stay in the future.
Stayed 7 nights in Feb 2024
Verified review

10/10 Excellent

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

Amazing Property and Location

We had a great time at this property, highly recommend! Views we’re amazing from all balconies/decks and the location was perfect for restaurants, shopping, etc. Mike the host was very helpful and we hope to stay here in the future!
Stayed 7 nights in Feb 2023
Verified review

10/10 Excellent

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

Beautiful Islamorada home

This property is beautiful and very spacious. It was excellent for a multi generational family holiday reunion.
Stayed 7 nights in Dec 2021
Verified review

10/10 Excellent

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

Awesome Beach House!

The place was clean with great views and lots of stuff to do on the property. You won't be disappointed staying here. We will definitely be back!
Stayed 7 nights in Feb 2022
Verified review

8/10 Good

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

Amazing property

Very well appointed vacation home. Stuff for all ages to do on the property and the laid back location was excellent just for relaxing at its best. Grandkids really enjoyed activities on the property. This place is a must for a relaxing vacation.
Stayed 7 nights in Jun 2024
Verified review

10/10 Excellent

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

Paradise in the Keys

We love the property the view was amazing and the house was amazing. Looking ditto another vacation in this beautiful beach home again in the future.
Stayed 7 nights in May 2022
Verified review

10/10 Excellent

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

Stunning inside and out

What a beautiful home! The property had everything we needed to buy some groceries and stay on-site (although we did some exploring and a boat cruise). The pool and hot-tub were the center of our evenings. Would highly recommend to anyone staying in the Keys.
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

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

Immaculate home!!

Immaculate beachfront home with amazing views! We had a party of 8 (4 couples) and it was more than enough room! Loved the amenities and location!! We would definitely stay here again!
Stayed 7 nights in Apr 2021
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