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Summerland Breeze - Three house retreat, perfect for multiple families

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Property grounds
Smart TV, DVD player, books, printers
On the beach
Exterior
7 bedrooms, desk, iron/ironing board, free WiFi

Reviews

10 out of 10
Exceptional

Entire home

7 bedrooms5 bathroomsSleeps 14

Popular amenities

  • Dryer
  • Hot tub
  • Washer
  • Parking available
  • Pool
  • Pet-friendly

Explore the area

Map
Summerland Key, FL
  • Florida Keys Beaches
    ‪1 min walk‬
  • Crab Key
    ‪12 min walk‬
  • Upper Sugarloaf Key
    ‪10 min drive‬
  • Key West, FL (EYW-Key West Intl.)
    ‪34 min drive‬

Room options

About the area

Summerland Key

On the beach.Within a 15-minute walk of the vacation home, you'll find Florida Keys Beaches and Crab Key. Also, Pye Key is within 2 miles (3 km) and Coupon Bight Aquatic Preserve is within 6 miles (10 km).
View more Vacation homes in Summerland KeyOpens in a new window

What's nearby

  • Florida Keys Beaches - 1 min walk - 0.1 km
  • Crab Key - 12 min walk - 1.1 km
  • Upper Sugarloaf Key - 10 min drive - 10.2 km
  • Key West Visitors Center - 12 min drive - 11.4 km
  • Sugarloaf Beach - 24 min drive - 21.5 km

Getting around

  • Key West Intl. Airport (EYW) - 34 min drive

Restaurants

  • ‪Mangrove Mama's - ‬10 min drive
  • ‪Boondocks Grille & Draft House - ‬5 min drive
  • ‪Kiki's Sandbar - ‬8 min drive
  • ‪The Square Grouper Bar & Grill - ‬6 min drive
  • ‪Looe Key Tiki Bar & Grill - ‬6 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Summerland Breeze - Three house retreat, perfect for multiple families

Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property....two cottages (each two-bedroom) and a main house overlooking the ocean. Located between the houses is a breathtaking resort-style pool, diving pool, and hot tub.

Minimum 28-day rental. NO, this is NOT available to rent for fewer than 28 nights. Please don't ask.

NEW May 2022: exterior of homes has been painted a beautiful Keys blue. ALL new doors and windows have been installed. (Photos have not yet been updated). Ice maker, and chest freezer available at an additional fee. Pool heating available for additional fee.

Surveillance cameras located throughout exterior of property for security reasons. No cameras inside interior areas or overlooking pool/hot tub area.

Property manager

Randy and Emily Hassler

Similar properties

Exterior

Summerland Nest - Ocean view with private beach and pool

  • Pool
  • Kitchen
  • Washer
  • Free WiFi
4.5 out of 5, Wonderful, 2 reviews
Summerland Nest - Ocean view with private beach and pool

Property amenities

Beach

  • On the beach

Pool/Spa

  • Heated pool
  • Hot tub
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Kitchenette
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 7 bedrooms
  • Bedsheets provided

Bathroom

  • 4.5 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • DVD player
  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair
  • Printer

Comfort

  • Air conditioning

Pets

  • Pet friendly
  • Welcoming dogs only
  • 3 pets total

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the bay
  • Near the ocean
  • On the waterfront

Things to do

  • Heated pool
  • Jet skiing nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

Policies

Check-in

Check-in time starts at 5:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 3 pets
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

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: 20
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 20. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

Property Registration Number DWE5404797

Property is also known as

Resort Style Three House Retreat

Summerland Breeze - Three house retreat, perfect for multiple families Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 5 out of 5 reviews
Rating 8 - Good. 0 out of 5 reviews
Rating 6 - Okay. 0 out of 5 reviews
Rating 4 - Poor. 0 out of 5 reviews
Rating 2 - Terrible. 0 out of 5 reviews

9.2/10

Cleanliness

Reviews

10/10 Excellent

Jim G.

Liked: Cleanliness

Summerland Breeze

Beautiful oceanfront property with wonderful pool - great space for large families
Stayed 30 nights in Mar 2025

10/10 Excellent

Matt P.

Great trip!

Great location, house was fun, would like to rent it again!
Stayed 28 nights in Jun 2022

10/10 Excellent

sheila l.

Liked: Cleanliness

Vacation of a lifetime

This is the perfect house for a large family! we have 4 adult children and it was perfect with the cottages to have all of us in one place. Tonio's ( at end of road) was a great spot for dinners and with it just 23 miles from Key west and Marathon it was nice being in the middle. We hit Duval on weekdays then took a trip to Sunday Funday at sunset grille in Marathon on Sunday's. Like I said it was the perfect vacation home and we would definitely book this dream home again!
Stayed 28 nights in Feb 2022

10/10 Excellent

Danielle N.

Liked: Cleanliness

Paradise Found

I remember this place being a dream rental 20 years ago. So glad it is back in the vacation rental pool. It was all I'd dreamed it would be and more. You can tell this paradise was designed with heart and with great detail. Very clean, very family friendly. We did bring two boats 36' Yellowfin for offshore fishing and 24' Carolina Skiff.

10/10 Excellent

Stacie B.

Liked: Cleanliness

Sweet Summer Time

We had THE BEST experience staying at Emily and Randy’s place from beginning to end! They are great people to work with and communicate very well pre-arrival and during the stay. We live in SW Florida and take our summers down to the Keys for the last 8 years. We rent a home 6-8 weeks while there and rotate our friends and family to visit with us. This home was by far the best we’ve ever rented. Neighborhood was safe and quiet. The property was very spacious with the most beautiful flowers and plants everywhere! The pool and porch area being enclosed by the screen was a huge plus when it comes to keeping the bugs away at dusk. The open water view was incredible! Entertaining guests in and out for a few weeks is a chore and having the separate cottages for families to spread out was a genius set up and it allowed some quiet time for me in the main house too ☺️ We only came across a couple of downfalls while there. We brought our 31 ft boat. Having a private basin to store the boat was AMAZING! However, it was a bit too big for the scenario. Going in and out in high tide worked fine, low tide we hit bottom a couple times. Also when we pulled out during a Northwest wind it was tricky keeping the boat in the dug out channel. Also extremely tight to turn the boat around in basin. We did it thanks to my husbands boat skills but I closed my eyes and couldn’t watch each time. Lol Overall, This house comes highly recommended by us! 😎☀️🌴
Stayed 42 nights in Jun 2021