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Summerland Breeze - Three house retreat, perfect for multiple families

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Summerland Breeze
View upon entering property.
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Amazing views.
View from above the house.

Reviews

10 out of 10
Exceptional
7 bedrooms4+ bathroomsSleeps 14

Popular amenities

  • Dryer
  • Hot tub
  • Washer
  • Parking available
  • Pool
  • Barbecue grill

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

Rooms & beds

7 bedrooms (sleeps 14)

Master Bedroom

1 King Bed

The Boat Room

1 King Bed

The Fish Room

2 Single Beds

The Mermaid Room

2 Single Beds

The Ocean Room

1 King Bed

The Relax Room

1 King Bed

The Starfish Room

2 Single Beds

4 bathrooms, 1 half bathroom

Bathroom - Lower Level

Towels provided · Toilet · Shower only

Cottage One Bathroom

Towels provided · Toilet · Shower only

Cottage Two Bathroom

Towels provided · Toilet · Shower only

Master Bathroom

Towels provided · Bathtub or shower · Bathtub · Toilet · Jetted bathtub · Hair dryer

Powder Room

Towels provided · Toilet

Spaces

Deck or patio
Kitchen
Kitchenette
Balcony
Outdoor play area
Dining area

About this property

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

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Pet-friendly

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House Rules

Check in after 5:00 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

Events allowed: family gatherings, birthday parties, weddings
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Pets

Pets allowed: dogs (limit 3 total)
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Smoking

Smoking is not permitted

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 that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
Property Registration Number DWE5404797

About the area

Summerland Key

Located in Summerland Key, this holiday home is on the beach. Florida Keys Beaches and Coupon Bight Aquatic Preserve reflect the area's natural beauty and area attractions include Blue Hole and Big Munson Island. With jet skiing, scuba diving and snorkelling nearby, you'll find plenty of adventures in the water.
Map
Summerland Key, FL

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, FL (EYW-Key West Intl.) - 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

Frequently asked questions

Does Summerland Breeze - Three house retreat, perfect for multiple families have a pool?

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

Is Summerland Breeze - Three house retreat, perfect for multiple families pet-friendly?

Yes, this property allows dogs (limit 3 total).

What time is check-in at Summerland Breeze - Three house retreat, perfect for multiple families?

Check-in begins at 5:00 PM.

What time is check-out at Summerland Breeze - Three house retreat, perfect for multiple families?

Checkout is at 10:00 AM.

Where is Summerland Breeze - Three house retreat, perfect for multiple families located?

Situated on the beach, this holiday home is within a 15-minute walk of Florida Keys Beaches, Crab Key and Pye Key. Coupon Bight Aquatic Preserve and Venture Out Keys are also within 6 miles (10 km).

Reviews

10

Exceptional

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

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Jim G.

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

Summerland Breeze

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

10/10 Excellent

Matt P.

Liked: Check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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

About the host

Hosted by Randy and Emily Hassler

Host profile image

Why they chose this property

This property is unique and beautiful in many ways....incredible ocean views, one-of-a-kind pool area (fully screened-in), and ample living space. Summerland Key is a lovely, quiet neighborhood, located just 25 miles from the heart of Key West (40 minute drive to Mallory Square, 25 minute drive to Key West Airport.

What makes this property unique

Three homes on the property make this a perfect option for multiple families, providing closeness and privacy at the same time.