See all properties
Entire home

A Tropical Luxury Getaway, Your own private resort!!

Family-friendly stay with outdoor pool in Summerland Key

Choose dates to view prices

Photo gallery for A Tropical Luxury Getaway, Your own private resort!!

A boat deck with seating, a small table with a drink, and a view of the water with other boats.
A clear view of a beach with shallow water and distant land.
A beach view with a pool, lounge chairs, and palm trees.
A room with a large window overlooking a body of water, palm trees, and a distant shoreline.
Exterior

Reviews

10 out of 10
Exceptional

Entire home

6 bedrooms7 bathroomsSleeps 16

Popular amenities

  • Ocean view
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

View in a map
Little Torch Key, FL
  • Place, Big Pine Key Flea Market
    ‪3 min drive‬
  • Place, National Key Deer Refuge Visitor Center
    ‪4 min drive‬
  • Place, Coupon Bight Aquatic Preserve
    ‪4 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪47 min drive‬

Room options

About the area

Summerland Key

Oceanside stay.You'll find Boondocks Grille & Draft House and Big Pine Key Flea Market within 3 miles (5 km) of this vacation home. Also, National Key Deer Refuge Visitor Center is within 3 miles (5 km) and Key West Visitors Center is within 6 miles (10 km).
View more Vacation homes in Summerland KeyOpens in a new window

What's nearby

  • Big Pine Key Flea Market - 3 min drive - 4.0 km
  • National Key Deer Refuge Visitor Center - 4 min drive - 4.6 km
  • Coupon Bight Aquatic Preserve - 4 min drive - 4.3 km
  • Key West Visitors Center - 5 min drive - 6.3 km
  • Florida Keys Beaches - 8 min drive - 8.7 km

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 33 min drive

Restaurants

  • ‪No Name Pub - ‬9 min drive
  • ‪Boondock's Grille & Drafthouse - ‬3 min drive
  • ‪Morning Joint - ‬10 min drive
  • ‪Kiki's Sandbar - ‬3 min walk
  • ‪Pop's Smoke Shed - ‬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.

A Tropical Luxury Getaway, Your own private resort!!

For more pictures on this property look us up on Instagram at sterlingbayhouse. This house is located on the open water with private dock and private in ground pool has five (5) bedrooms with king size beds with private bathroom and the 6th bedroom with three (3) queen size beds and their own bathroom. Bedroom six (6) with queen size beds has Foosball and Shuffleboard game table. All bedrooms have their own smart TV's to log into whatever platform you may need. Full kitchen with dining room, and spacious exterior porch. Downstairs you will have plenty of seating with table and chairs, couches, loungers by pool area, beach cabanas, hammock, and two tiki huts to relax under. Bar area under home has big screen tv to watch the games on with a commercial ice machine, poker table with roulette wheel, darts, and Pac man machine for the kids or kids at heart still. Fishing poles, light tackle, Ping Pong table under home, paddle boards (2), kayaks (5) and beach cruisers (6) to ride around on. Receiver in bar area to play local radio stations or bluetooth connectivity with speaker all over the back yard.

Similar properties

Pool
Sugarloaf Key RV Resort & Cottages
Summerland Key
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
4.7 out of 5, Exceptional, 26 reviews
Sugarloaf Key RV Resort & Cottages

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Pool/Spa

  • Heated pool
  • 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
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Chef service
  • Dining table

Bedrooms

  • 6 bedrooms
  • Bedsheets provided

Bathroom

  • 6.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed
  • Note from host: Outdoors only! Absolutely no smoking in the house.

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • Near a hospital
  • Near an outlet shopping mall
  • Near the ocean
  • On the waterfront

Things to do

  • Arcade/game room
  • Bicycles
  • Foosball table
  • Gym
  • Heated pool
  • Kayak
  • Table tennis
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks 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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles

Policies

Check-in

Check-in time starts at 4:00 PM

Check-out

Check-out before 10:30 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Take out the trash
Turn off the lights
Failure to complete these may result in a negative review from the host.

Rules

Absolutely do NOT open and leave open windows and doors!!!
No Smoking in house .

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

Events allowed: family gatherings, birthday parties, weddings
Noise Ordinances go into affect 10:00 PM

Smoking

Smoking is not permitted
Outdoors only! Absolutely no smoking in the house.

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: 40
Note from host: Noise Ordinances go into affect 10:00 PM
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, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 40. Note from host: Noise Ordinances go into affect 10:00 PM For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Frequently asked questions

How close is A Tropical Luxury Getaway, Your own private resort!! to the airport?

This vacation home is 23.3 mi (33-min drive) away from the Marathon, FL (MTH-Florida Keys Marathon) airport, the closest popular airport to the property.

Does A Tropical Luxury Getaway, Your own private resort!! have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is A Tropical Luxury Getaway, Your own private resort!! to the beach?

This vacation home is 7.1 mi (15-min drive) from Florida Keys Beaches and 8.2 mi (12-min drive) from Loggerhead Beach. Don't forget your sunscreen!

Does A Tropical Luxury Getaway, Your own private resort!! offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at A Tropical Luxury Getaway, Your own private resort!!?

No, there is no casino at this vacation home.

What time is check-in at A Tropical Luxury Getaway, Your own private resort!!?

Check-in begins at 4:00 PM.

Is there free parking at A Tropical Luxury Getaway, Your own private resort!!?

Free parking is not available at this vacation home.

Does A Tropical Luxury Getaway, Your own private resort!! have a pool?

This vacation home features an outdoor pool.

Does A Tropical Luxury Getaway, Your own private resort!! have a spa?

There are no spa services available at this vacation home.

How close is A Tropical Luxury Getaway, Your own private resort!! to downtown Summerland Key?

This vacation home is 3.7 mi away from Summerland Key.

A Tropical Luxury Getaway, Your own private resort!! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 54 out of 55 reviews
Rating 8 - Good. 1 out of 55 reviews
Rating 6 - Okay. 0 out of 55 reviews
Rating 4 - Poor. 0 out of 55 reviews
Rating 2 - Terrible. 0 out of 55 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

McKell G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing host, beautiful house and property!
Stayed 7 nights in Feb 2026
Verified review

10/10 Excellent

Nancy A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Sterling Bay House is truly a private resort. It was impeccably clean, with lovely rooms; the kitchen was well-stocked, the beds comfortable. Our family loved the pool (best ever), the fun oceanfront with cabanas, hammock, its own sand beach, and the expansive dock for fishing. Brava!
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

Tomi S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house, pool and amenities!
Stayed 7 nights in Jan 2026
Verified review

10/10 Excellent

Iven T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host had everything covered and was very responsive when we had a question. The amenities were fantastic.
Stayed 6 nights in Jan 2026
Verified review

10/10 Excellent

Mary W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was spotless, well stocked and well labeled. The Sterling Bay House exceeded our expectations. A large group of 16 gathered for a family re-union to celebrate a 70th birthday with an age range from 19 months to 86 years. Plenty of fun things to do within 40 minutes of the house.
Stayed 6 nights in Mar 2026
Verified review

10/10 Excellent

Larry P.

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

Family Vacation

Everything we needed to have a great vacation was provided. Super nice place!We would stay here agin
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

Katherine D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wow! What a house! We had so much fun and while we left a few times, really no need with the amenities and location. It’s everything the pictures show.
Stayed 6 nights in Dec 2025
Verified review

10/10 Excellent

Nancy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a great place to stay. The kitchen was well stocked and organized. There were more beach towels than you could ever use. The sleeping arrangements/bedrooms were great for a large group. The swimming pool, pool toys, and games were amazing. And..the host was great about responding and helping. For a relaxing and fun place to be with young kids you can’t go wrong.
Stayed 6 nights in Nov 2025
Verified review

10/10 Excellent

Heather L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My family and I stayed at the Sterling Bay House from March 27th to April 3rd. This property is amazing! The house was impeccably clean and beautifully decorated. The outside was awesome as well. So many amenities come with this house inside and out. From the various games we played, attempting to paddleboard, and fishing on the dock. We even rode bikes the one day (two we couldn't use- one had a flat tire and the other the chain kept popping) but we still had fun. Both the children and adults were never bored. We had one small issue with the heated pool. Steven was quick to respond and came right over and fixed the problem. We went for a very short walk to Kiki's one night. Loved the atmosphere, the food was delicious, and great service. We had so much fun, lots of laughs, and many memories made! Thank you Steven!
A beautiful view every day!
Stayed 7 nights in Mar 2026
Verified review

8/10 Good

HARRY H.

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

KEYS VACATION 2025

The house and pool were very nice.
Stayed 7 nights in Mar 2025
Verified review

10/10 Excellent

JD

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

Spring Break in Little Torch Key

This is by far the best property we've found in the Keys. The layout was perfect for our group and the outdoor space was amazing. The owner was very responsive to any questions we had. We will definitely stay here again when we come back.
Stayed 7 nights in Mar 2025
Verified review

10/10 Excellent

alexander v.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This place is amazing and fully equipped/outrigged. The listing is exactly as stated and beautiful. Very active marine wildlife and warm clear Florida key's water. Owner is very responsive and nice. Kiki's just a two-minute walk away and great restaurants a very quick drive. Everyone in our party was amazed, had a blast, and were sad to leave. I can honestly say that it is the best property I've rented.
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

Amy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our family of 10 just spent a heavenly week at Sterling Bay House and we could not love this house more! The house itself is just incredible—spacious, well organized and thought out, beautifully decorated, with so many great amenities! It truly feels like a small private resort. The location on Little Torch Key is perfect—it feels private and secluded, yet it is just a short five minute drive to the grocery store and pickleball courts. It’s also in a perfect location for a day trips to Key West or Marathon, which came in handy when we had a couple of windy days. None of us were ready to leave Sterling Bay House at the end of the week! We are also so impressed with the owners, Steve and Whitney. Steve is super responsive and helpful, and quickly fixed a couple of very minor issues that popped up. He’s also just a genuinely nice guy! We would highly recommend SBH to others, and will hopefully be returning ourselves sooner rather than later!
Stayed 7 nights in Jan 2026
Verified review

10/10 Excellent

Greg W.

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

Living the Life!

We loved every minute of our stay at Sterling Bay House! The house is a well appointed fulfilling all our needs! We were nine adults and five kids. There were fun things for the kids to do. The kids (and adults) loved the pool, we enjoyed being on the dock and fishing, enjoyed all the games for the outside, enjoyed the kayaks. We had iguana visits and key deer! We would definitely stay there again!
Stayed 7 nights in May 2025
Verified review

10/10 Excellent

Craig C.

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

Family Vacation

Great property and location. House is designed and built perfectly for family or multiple couples. It has all the amenities you could hope to enjoy. Great hosts and very helpful. We left a couple of articles of clothing and they graciously sent them to us. Highly recommend.
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

Ronda S.

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

Family Christmas

Awesome property - everyone had plenty of room and never felt crowded. Amenities were endless. Welcome basket was nice. Plenty of everything from dishes to silverware- to pots/pans to towels. Location is perfect~everything was within great proximity. The warm pool was enjoyed by all.
Stayed 7 nights in Dec 2024
Verified review

10/10 Excellent

Minette T.

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

Perfect Paradise

Perfect vacation for our three families! The house was gorgeous and well stocked with all of the nice little extras! Clean and comfortable, and the owner was extremely helpful and responsive with questions. Our own little mini resort with kayaks, corn hole, pool games, fire pit and bikes all included. Thank you for the hospitality!
Stayed 6 nights in Dec 2022
Verified review

10/10 Excellent

Susan K.

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

Excellent Venue

The Sterling Bay House was absolutely beautiful and I would highly recommend it to anyone. Our daughter had a small family wedding at the venue and it was absolutely gorgeous. The owners were very friendly and timely in responding to any questions we had and even went above and beyond to have all the dinnerware, glassware and silverware for the event. The location was very convenient to restaurants and stores and only a half hour or so to Key West.
Stayed 7 nights in Mar 2023
Verified review

10/10 Excellent

Tracy V.

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

Another Perfect Year at Summerland House!

We had another amazing stay this year! Such a wonderful house for the whole family! It has it all from stunning coastal views, private beach and pool! Very close to local restaurants, snorkeling, a great dock for a boat and fishing. The house is tucked in, and perfect o just relax with a tropical drink in hand! They also have kayaks, fire pit, and a room downstairs, with all kinds of fishing gear, poles, big coolers and amazing Ice maker. Perfect for a big family or group, every room has a bathroom, towels for inside and out! Wonderful game room, spacious kitchen and living room! The hosts are incredibly responsive and always make us feel right at home!We can't wait to come back next year!
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Steve P.

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

First Class Property!!!!

This property has it all! From the pool to the dock! Even has a large ice maker and a bait freezer! Left our boat in the water all week. Great location! This is our second time staying in the Sterling bay house and will definitely book it again in the future!
Stayed 8 nights in Jul 2024
Verified review

10/10 Excellent

Joe B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an absolutely incredible stay at this Little Torch Key beach front property. It’s easily one of the best VRBO experiences we’ve had.The house itself is beautiful, new, and extremely well thought out. It’s very spacious and comfortably accommodated our group without ever feeling crowded. Everything was clean, organized, and clearly designed with guests in mind.One of the standout features is the pool, private beach and long dock. We had a boat delivered for the duration of our stay and kept it docked right outside the house, which made the whole trip that much better. Being able to hop on and off the boat whenever we wanted was a huge plus.The property also came equipped with fishing rods and tackle, and even a deep freezer for storing bait. Small details like that really made a difference. We spent a lot of time out on the water snorkeling, fishing, and anchoring at nearby sandbars. The surrounding waters are absolutely beautiful.Location-wise, it’s hard to beat. You’re just a short 2 minute walk to Kiki’s Sandbar & Grille, which quickly became one of our favorite spots for food, drinks, and live music.The owners were fantastic—very responsive, helpful, and genuinely great to work with from start to finish.Between the house, the setup, the location, and the overall experience, everything about this trip was just about perfect. We would absolutely stay here again and highly recommend it to anyone looking for a relaxing and memorable stay in the Keys.
Stayed 7 nights in Mar 2026
Verified review

10/10 Excellent

Kayley H.

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

Kansas/Texas Annual Keys Trip

This is year four for our annual family Florida trip and year two at Sterling Bay House. We LOVE this house! The area is nice; the house is beautiful and clean, full of the necessary amenities, and conveniently located. It’s a mini resort that we call home for a week. The host is super accommodating and communicative. We will be back!
Stayed 7 nights in Jun 2023
Verified review

10/10 Excellent

elizabeth k.

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

Exceptional property

The Sterling Bay House was just perfect for our family Christmas in the Keys! Lots of space and a well appointed kitchen (with two dishwashers!) took care of all our needs inside. Outside, the property absolutely shined: pool, cabanas, grill, dock, paddle boards, bikes, kayaks. They thought of everything and we had a wonderful family holiday. Thank you SBH!
Stayed 7 nights in Dec 2022
Verified review

10/10 Excellent

Erika W.

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

Practically perfect in every way!

What a blessing for our group of friends and family to gather and share time and space at Steven’s home. From start to finish it was easy, comfortable, and luxurious! The home is immaculate and full of sweet creative details. We were a group of 12 with ages 7-75 and everyone had everything that they could need or want! We would love to return again for more fun:)
Stayed 5 nights in Mar 2022
Verified review

10/10 Excellent

Verified traveller

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

The best house and property

We have stayed at a lot of houses together with our cousins and this was probably our favorite! The house itself was gorgeous and clean with every appliance and thing you could need. The owners really put thought into every detail. The house was decorated beautifully. The beds were super comfortable. The pool was incredible. The beach area and dock were so much fun. We enjoyed snorkeling, kayaking, swimming, and playing darts and other games. Thank you so much! We would love to come back.
Stayed 6 nights in Apr 2023