Entire home

Ocean Front Luxury Vacation Rental Near Key West

Choose dates to view prices

Photo gallery for Ocean Front Luxury Vacation Rental Near Key West

A heated pool
Interior
Property grounds
Game room
Fridge, microwave, oven, stovetop

Reviews

9.4 out of 10
Exceptional

Entire home

4 bedrooms5 bathroomsSleeps 84006 sq ft

Popular amenities

  • Dryer
  • Hot Tub
  • Washer
  • Parking available
  • Pool
  • Kitchen

Explore the area

Map
Sugarloaf Key, FL
  • Upper Sugarloaf Sound
  • Upper Sugarloaf Key
    ‪3 min drive‬
  • Florida Keys Beaches
    ‪16 min drive‬
  • Key West, FL (EYW-Key West Intl.)
    ‪34 min drive‬

Room options

About the neighborhood

Summerland Key

This vacation home places you next to Upper Sugarloaf Sound and within a 15-minute walk of Upper Sugarloaf Key. The vacation home includes a private pool, a kitchen, and a balcony.

What's nearby

  • Upper Sugarloaf Key - 3 min drive - 0.9 miles
  • Florida Keys Beaches - 16 min drive - 7.0 miles
  • Sugarloaf Beach - 17 min drive - 7.4 miles
  • Boca Chica Nude Beach - 34 min drive - 15.7 miles
  • Duval Street - 39 min drive - 24.1 miles

Getting around

  • Key West Intl. Airport (EYW) - 27 min drive

Restaurants

  • ‪Mangrove Mama's - ‬4 min drive
  • ‪Baby's Coffee - ‬10 min drive
  • ‪The Square Grouper Bar & Grill - ‬8 min drive
  • ‪Galley Grill - ‬11 min drive
  • ‪My New Joint - ‬8 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.

Ocean Front Luxury Vacation Rental Near Key West

Luxury Villa of the Setting Sun

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

🌓 Oceanfront Event Venue & Luxury Vacation Rental Near Key West

A Private Paradise for Weddings, Retreats, Reunions & More

Welcome to your exclusive oceanfront escape—an unforgettable event venue and luxury vacation rental just 18 miles from the charm and energy of Key West. With breathtaking ocean views, total privacy, and world-class amenities, this stunning estate offers the perfect setting for your next celebration or gathering.

āø»

🌊 A Dream Setting for Any Occasion

Whether you’re planning a beachfront wedding, a corporate retreat, a milestone birthday, or a wellness escape, this secluded waterfront property offers unmatched beauty and flexibility.
•Private sandy beach with panoramic Gulf views
•Expansive outdoor spaces for ceremonies, receptions, or group activities
•Heated saltwater pool and hot tub with sun loungers and shaded seating
•Covered lanai with outdoor dining and wet bar for effortless entertaining
•Space to accommodate tents, live music, photo booths, or yoga sessions
•On-site parking for guests and vendors

āø»

šŸ’Ž Amenities That Elevate Every Stay

This property is packed with premium amenities designed for comfort, relaxation, and entertainment:
•Chef’s dream kitchen with oversized refrigerator, wine fridge, large island, and top-of-the-line appliances
•Game room with pool table, poker table, air hockey, arcade games, and a wet bar
•Spa-inspired sauna for unwinding after a full day of events or adventures
•Kayaks and paddleboards to explore the sparkling waters right from your private beach
•Smart TVs in every room, high-speed WiFi, and full laundry facilities

āø»

šŸ›Œ Luxurious Accommodations – Sleeps 8

Every bedroom is a private sanctuary, offering comfort and style for overnight guests:
•Four elegant bedrooms, each with its own en suite bathroom
•Spa-style features including soaking tubs, walk-in showers, and bidets
•Select rooms feature private balconies with sunrise or sunset views
•Premium linens, stylish decor, and central A/C throughout

āø»

šŸ“ Prime Location Near Key West

Enjoy the perfect mix of seclusion and accessibility—surrounded by nature, but just a short drive to vibrant attractions:
•Explore the Great White Heron and Key Deer Wildlife Refuges
•Visit the Ernest Hemingway Home, Mallory Square, and Duval Street
•Charter a boat, go fishing, or enjoy snorkeling adventures nearby

āø»

🌟 Host Unforgettable Moments

This is more than a rental—it’s a destination designed for memories. From casual beach barbecues to elegant waterfront weddings, every detail of this estate sets the stage for something truly special.

šŸ“… Now accepting event bookings and vacation stays.
šŸ”— Contact us or Book your stay to start planning your dream getaway.

🚨 Important Note: Allergy-Friendly Property

To ensure a safe and healthy environment, this home cannot accept animals of any kind, including service animals, due to the owner’s severe allergies. We appreciate your understanding and cooperation in maintaining the well-being of all guests.

🌊 Book your stay today and experience oceanfront luxury like never before! 🌊

Things to Know
Check-in time: 4:00 p.m.
Check-out time: 10:00 a.m.
All guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.
No smoking is permitted anywhere on the premises.
Absolutely do NOT open and leave open windows and doors!!!
Guests must travel by car to reach this home.

What's nearby
* Sugarloaf Beach - 0 min walk
* Most beautiful Sunset in the hemisphere ( private ) - you are there
* Flager Bridge is seen from the property
* National Key Deer Refuge Visitor Center - 4 min drive
* Big Pine Key Flea Market - 4 min drive
* Key West Visitors Center - 6 min drive
* Coupon Bight Aquatic Preserve - 9 min drive
* Florida Keys Beaches - 15 min drive

Parking notes: There is free parking available for 10 vehicles.

Security camera details: Four external cameras are around the perimeter of the home.

Dock details:
2 days notification is required in order to heat the pool and pool spa. A fee of USD 32 per day must be paid prior to check-in to purchase pool and pool spa heat for your stay.


Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the ā€œDamage Waiverā€). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
The vacation home is air-conditioned and features a kitchen, 4.5 bathrooms, and a balcony. There's space to spread out with 4 bedrooms and a dining area. Guests can expect to find a TV with a DVD player. Other standard amenities include a private pool, a washing machine, and a coffee maker.

Property manager

Vacasa of Florida

Languages

English, French, German, Italian, Spanish

Similar properties

Property amenities

Beach

  • On the beach

Pool/Spa

  • Heated pool
  • Hot tub
  • Massage
  • Private pool
  • Sauna

Internet

  • Available in the house: Internet access

Parking and transportation

  • Car required
  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Wet bar

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 4.5 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Living room
  • Separate dining area

Entertainment

  • Books
  • DVD player
  • Games
  • Stereo
  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property
  • Note from host: Smoking is not permitted anywhere on the premises.

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • In a rural location
  • In a village
  • Near a hospital
  • Near the bay
  • Near the marina
  • Near the ocean
  • On the waterfront

Things to do

  • Arcade/game room
  • Billiards/pool table
  • Foosball table
  • Heated pool
  • Kayak
  • Table tennis
  • Water sports equipment
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing 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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden
  • Property located in a resort
  • Unit size: 4,006 square feet

Policies

Check-in

Check-in time starts at 4:00 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

  • This property doesn't allow pets

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
Onsite parties or group events are strictly prohibited
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 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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Property is also known as

51318

Frequently asked questions

What's there to see around this vacation home?

This vacation home is located in Summerland Key, just steps from Upper Sugarloaf Sound. You'll also find Upper Sugarloaf Key and Lower Sugarloaf Sound within a short drive.

Is parking available on site at this vacation home?

Yes, there is a garage.

Is there a spa available at this vacation home?

Spa services at the vacation home include massages.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there is a hot tub.

What amenities will couples enjoy at Ocean Front Luxury Vacation Rental Near Key West?

Amenities that appeal to couples at this beachfront vacation home include a private pool and a kitchen in each accommodation with some featuring ocean views.

Are there hot tubs at Ocean Front Luxury Vacation Rental Near Key West?

Yes, this vacation home has a spa tub.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Does this vacation home have connecting rooms?

No, this vacation home doesn't feature connecting guestrooms.

How close is the airport from this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 17.8 mi away (27 minutes by car).

Are there rooms with balconies that I can book at Ocean Front Luxury Vacation Rental Near Key West?

Yes, every accommodation at Ocean Front Luxury Vacation Rental Near Key West comes with a balcony with some featuring ocean views.

Ocean Front Luxury Vacation Rental Near Key West Reviews

Reviews

9.4

Exceptional

Rating 10 - Excellent. 33 out of 43 reviews
Rating 8 - Good. 7 out of 43 reviews
Rating 6 - Okay. 3 out of 43 reviews
Rating 4 - Poor. 0 out of 43 reviews
Rating 2 - Terrible. 0 out of 43 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Stan V.

Liked: Cleanliness

Top Notch Experience

There are no words to describe how wonderful this property is! From the very beginning to the sad ending (because we had to leave), it was a fantastic location, and the house had everything we needed. We stayed in and cooked almost every night and the amenities never disappointed! The view cannot be overstated, and the sunset is beyond earthly! There were 7 of us and the house was large enough that we never felt cramped. There is no way to sit in all the spaces available! There were several reviews that the house was not maintained. We certainly did not have that experience. We've never stayed at a house that was so clean and had everything we needed. From the morning coffee to the evening sunset, this property will not disappoint! Would stay there again in a heartbeat! Book it NOW!
Stayed 5 nights in May 2025

10/10 Excellent

Lindsay G.

Liked: Cleanliness

The most beautiful home rental I've ever been to

This property is truly magical. We spent every day lounging by the pool and kayaking. At night, we would fish from our own private beach. We saw dolphins, small sharks and other marine life. The house is immaculate and equipped with everything you need for a relaxing vacation. Don't hesitate.
Stayed 3 nights in Apr 2025

10/10 Excellent

Shaun M.

Liked: Cleanliness
Stayed 6 nights in Feb 2025

10/10 Excellent

Dawn H., Tucson, AZ

Liked: Cleanliness

Candy to the Eye

Entering the Villa was pure ā€˜Candy to the Eye!’ All amenities were over the top. We absolutely loved the beach, kayaks and canoes. So much fun. The pool was fabulous. The outdoor furniture was so beachy, comfy and many fun seating arrangements. Enjoyed coffee on the balcony every morning. Views, views, views, just stunning. We would love to return to the Villa in the future and stay longer!
Stayed 5 nights in Jun 2024

6/10 Okay

Kurt D.

Great Property Lots of Video Cameras

Nice place, great views. Pool was supposed to be heated, heat pump was broke. Pool was dirty, was supposed to get cleaned on Tuesdays they said. Didn't get cleaned. No hot water to the kitchen sink. Young kid in charge of the property was responsive though. Lots of camera's. If you ever wanted to be on the reality show "Big Brother" this is the place for you. And they check them and call you if they see something they don't like. Kinda creepy but once you get past that its okay.
Stayed 4 nights in Apr 2024

6/10 Okay

hollee h.

Liked: Cleanliness

Beautiful home but..

The home is beautiful! It’s an amazing escape. However the pool heat did not work and vacasa the company that the property is managed by is absolutely horrible horrible horrible!!!! Gary Fields is this homes property manager and I spent my first 3 days of my vacation talking to vacasa reps and agents far more than I did enjoying my vacation allll while being given the runaround about how the pool would be fixed. It never was fixed and Gary actually ended up completely ignoring us altogether.the pool is one massive feature of this home so to not be able to enjoy it was heartbreaking!! I have never in my life had such a horrible experience with a property management company. They had zero regard for us given they’d already gotten our money for our stay. A home valued over several millions of dollars and they didn’t care at all to have the heat worked on or even looked at by anyone. We will never ever rent a place managed by vacasa ever again. No matter how nice the place is- they suck as a company when it comes to helping paying customers in need.
Stayed 5 nights in Mar 2024

8/10 Good

lindsey o.

Liked: Cleanliness

Perfect resort for a group of friends or family

This house is stunning and very secluded. We were there four nights to celebrate a friends 40th birthday and it did not disappoint. Four adult couples and a baby and we each had our own room with bathrooms within. The sunset from the pool was unbelievable each night. We swam, used kayaks and floated in ocean. If you plan to walk into ocean from private beach I would recommend water shoes. We did not utilize the game room because we had perfect weather and spent the whole trip outside around pool/beach. The house was spotless and had all supplies we needed for cooking throughout our stay. We did need to purchase more dish soap, garbage bags and toilet paper. On arrival we had our few hiccups. Vacasa happened to be at property thank goodness. We were told no early check in with a baby and found it odd that all the water was off as the owner thought we were coming the day after. They had said no early check in as cleaners would be there but how was all the water off? We also had no A/C on top level for maybe two hours, not a bit deal just combined with water and a few plumbing issues (water resolved almost immediately and broken toilet/sink fixed next day) was a small let down for price of house. Friday morning around 8 am a woman appeared in the house to ā€œcheck the fire extinguishersā€. This was a surprise no one mentioned. nothing beats the location and views of this for us. It was perfect for the relaxing trip we needed and about 25 from key west for night out and airport.
Stayed 4 nights in Nov 2023

8/10 Good

ANA V.

Liked: Cleanliness

Nice house, listing not accurate

The house is nice, although is surrounded by swampy area, it’s the only house on the water for miles, I’m assuming is hard to build in this type of land. The listing doesn’t show the aerial pictures, you get the address 2 days before your stay. Also, the house only provides coffee and soap; dish, hand and laundry soap, and not enough for 4 people staying for 5 days. The paper towel and toilet paper were very low quality, didn’t expect it for the type of house we rented. They didn’t provide any spices, not even salt and pepper, be prepare to go to the store and buy everything. The game room is very nice, and they also have pool toys for the kids. They have cameras outside, which we didn’t think it was appropriate. Overall we had a good time, but it didn’t meet our expectations.
Stayed 5 nights in Jun 2023

8/10 Good

Dawn H., Madison, Alabama

Liked: Cleanliness

Paradise

Pictures are 100% accurate!!! Only problem with this home is the road it’s on, when it rains it floods, and the 2 main level bedrooms would not cool like the rest of the house. Had to place a fan in the doorway of one room to cool it down.other than that had a great time
Stayed 8 nights in May 2023

10/10 Excellent

Rob M.

Liked: Cleanliness

Awesome place!

Everything was perfect!
Stayed 10 nights in Mar 2023

10/10 Excellent

Jamie R.

Liked: Cleanliness

Beautiful Place! Paradise!

This is the place to relax! Beautiful!!
Stayed 4 nights in Mar 2023

10/10 Excellent

Todd E.

Liked: Cleanliness

Exceeded every expectation.

Close enough to everything, and far enough for total privacy. Would definitely stay here again.
Stayed 5 nights in Aug 2022

8/10 Good

Katherine O.

Liked: Cleanliness

Gorgeous home, stunning views. Home was very clean and great pool.

We had a great time, house was lovely. Only thing keeping it from a 5 is the fact that while on the ocean, you really can’t swim in the ocean as it’s too shallow. We couldn’t get the Bluetooth speakers by the pool to work. House is very remote but there are a few restaurants nearby which are great. We drove to key west for dinner a number of times, easy 20 minute drive.
Stayed 10 nights in Jul 2022

10/10 Excellent

Tomasz W.

Liked: Cleanliness

Privacy

I really enjoyed the privacy , no busy neighborhoods, quiet and secluded location. House is very well designed and decorated. Private beach, and onsite pool makes this place a really special. Just a short drive to the Key West with it’s restaurant’s and busy bar's. We’ll definitively be back for the longer stay.
Stayed 4 nights in Jul 2022

8/10 Good

Verified traveler

Liked: Cleanliness

Beautiful Property- needs a little maintenance

We really enjoyed the location and views of this gorgeous property. The layout and amenities that it has to offer are second to none. Only reason for a little lower review, is the maintenance of the property…. Several loose tiles in the showers and warped / damaged baseboards in restrooms. Also the outdated / not working grill. Given the cost per night/ week, these items really need to be addressed.
Stayed 5 nights in Jun 2022

10/10 Excellent

thomas n.

Liked: Cleanliness

Your family will love it

This house is SICK! Pictures do not do it justice. Your friends and family will love it!
Stayed 15 nights in Jan 2022

10/10 Excellent

Melanie L.

Liked: Cleanliness

Gorgeous vacation home

Our family of 8 adults thoroughly enjoyed the week. Beautiful spaces for rest, relaxation and play. The pool and hot tub were as spectacular as they look in the pictures, and the beachy ocean access was a great place for corn hole games, lounging in the sun and fishing - so quiet and secluded. We rented paddle boards for a few days to explore a little further out around the shore. The game room is one of the best amenities - it was the perfect place to hang out together after dinner for loads of fun. Key West is only a short drive so you can get your party fix. There are many closer places for great meals though. We loved having lunch at Mangrove Mama’s just around the corner, and for a great steak dinner don’t miss Grill - just north on Rt 1.
Stayed 7 nights in Dec 2021

10/10 Excellent

Patrick H.

Liked: Cleanliness

Could use bathroom on ground floor and instructions to run tv's etccc

Fantastic
Stayed 7 nights in Dec 2021

10/10 Excellent

Paul L.

Liked: Cleanliness

Great getaway!

Super location very laid back and away from the hustle of the Keys
Stayed 4 nights in Jul 2021

10/10 Excellent

Steve W.

Villa of the setting Sun

Amazing home, seclusion, natural habitat and amazingly responsive customer service to a few small issues with storm related items. Great job Vacasa! We would highly recommend this property and property manager. Thanks Carol at Vacasa, you were so kind!!
Stayed 5 nights in Jul 2021

10/10 Excellent

Kelley C.

Incredible home!!!

Incredible view, loved the beach, pool was perfect, outdoor seating for days. Commercial appliances all very nice. Wish it had more bedrooms so it slept more people as it will entertain many more than 8.
Stayed 5 nights in Jun 2021