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Places to stay in Sunset Key

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Vacation rentals for every style

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Popular amenities for Sunset Key places to stay

Self check-in
Gym
BBQ grill
Laptop-friendly workspace
Wifi

Other great vacation rentals in Sunset Key

Guest favorite
Two wooden chairs provide seating on the deck of the houseboat, facing the open waters of Key West. Large glass doors lead into the kitchenette area, with a view of the serene sea and sky, emphasizing the peaceful outdoor setting.
Houseboat in Key West
4.95 out of 5 average rating, 19 reviews

Shanty Pineapple Key West

KirstieRating, 5 stars1 week ago
Thanks to Tony for making our stay at the Shanty Pineapple was a wonderful experience! Everything was clean and how it was described in the listing! We had a great time celebrating our anniversary! The view of the sunrise and sunset each day was amazing! And the food delivery was extremely convenient! Thanks again Tony! Highly recommend!
Guest favorite
A modern countertop is highlighted by a bronze faucet, complemented by clear glass jars filled with yellow bath sponges. The backsplash features a subtle blue herringbone pattern, adding a refreshing touch to the serene bathroom environment.
Apartment in Key West
4.82 out of 5 average rating, 67 reviews

Blue Room at the Grand Maloney

DiegoRating, 5 stars2 weeks ago
Phenomenal place, the location was a big plus! you can walk everywhere. looking forward to staying again
Guest favorite
Houseboat in Marathon
5 out of 5 average rating, 19 reviews

Adventurers escape breathtaking off-grid houseboat

YulieskaRating, 5 stars2 weeks ago
Una gran experiencia, hermoso lugar. Joe fantastico. Siempre pendiente y dispuesto a ayudar.
Superhost
A charming tiny floating houseboat is anchored on clear turquoise waters, featuring a cozy wooden deck with storage crates. Distinct round windows and a circular doorway add character, while the structure's white exterior contrasts beautifully with the vibrant surrounding environment.
Houseboat in Key West
4.71 out of 5 average rating, 173 reviews

A slice of paradise in the Florida Keys

CarmenRating, 5 stars3 months ago
Wonderful night! Only a few bugs around dusk that left by nightfall. Lots of planes took off from 5-7 PM, but again they stopped by nighttime and not sure that it happens every day. The boat itself was perfect, exactly as described!
A sandy beach transitions to calm waters, framed by palm trees and greenery. Sun loungers are arranged neatly along the shore. A private spiral staircase leads to the beach, while a wooden dock extends into the water, inviting leisurely excursions.
Condo in Key West
4.91 out of 5 average rating, 82 reviews

Ocean Front Suite with Direct Beach Access

TerrenceRating, 5 stars1 week ago
It was a wonderful experience and the amenities and staff were great! Will 100% recommend the on site restaurants dinner menus (PRIME RIB!!). The 24 hr pool and hot tub access were also a nice touch. Allowed us to enjoy water activities during the day, and some cooler experiences in the evening away from the sun!
Top guest favorite
A private conch cottage floats on calm waters, featuring a light green exterior with white trim. Spacious decks are present at the front and back, while paddle boards and kayaks are visible nearby, highlighting the connection to the surrounding nature.
Houseboat in Key West
5 out of 5 average rating, 62 reviews

Key West Outpost: eco-vacation

FrankRating, 5 stars3 days ago
This place was a dream come true. Greta way to detach from the everyday stress and chaos. We loved everything from the tranquility to the scenery. We enjoyed kayaking and paddle boarding as well as some fishing. Saw some bonet head sharks and some barracuda. Caught some snapper. Can’t say it enough this place was amazing and will for sure be coming back. Thank you!!
Guest favorite
Two white chairs are positioned on a striped red and white deck, providing a cozy seating area. Sunlight reflects off the nearby water, and a canopy shades the upper deck in the background under a bright blue sky with scattered clouds.
Boat in Key West
5 out of 5 average rating, 21 reviews

“The Easy Way” Comfy, Practical, Convenient

ShawnRating, 5 stars2 weeks ago
In one word, Excellent! Or maybe Outstanding. Everything from location to communication and everything in between. Even got to see a nurse shark and barracuda swim by while sitting on the deck. Eric and his “team” really took care of us for the four full days. Warning though, if you prefer five star hotels, this is not for you. However, if you like to camp or want to relax, unwind, and get away from the day to day hassles then I would highly, highly recommend this. We also took advantage of Eric’s Fishy Business fishing charter. To quote the often to used cliche, we would do this again, in a heartbeat. We cannot emphasize enough how much we enjoyed this half of our vacation. So, if you are still reading this, book it!!
A concrete dock extends into the turquoise water, lined with lounge chairs for relaxation. A palm tree casts shade nearby, while the house's stairway leads up to a bright, elevated porch. The calm water sparkles under a clear sky.
Bungalow in Cudjoe Key
4.89 out of 5 average rating, 9 reviews

Oceanfront Bungalow Venture Out

DanaRating, 5 starstoday
I can surely say that this location had everything we were looking for. The view was incredible and the kids enjoyed fishing and snorkeling right off the dock. We saw many lobsters, tarpon, a nice sized shark, parrot fish, mangrove snapper and a grouper within the canal right at the house dockage. We chummed the water and had a blast catching smaller fish. There was a boat rental right across the bay and we made use of the house’s dock for 3 days. Extremely quiet street. We rarely saw neighbors from the porch. The community pool was nice, clean and cool. The house was clean and inviting. Great location and an overall great stay!
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Your guide to Sunset Key

Welcome to Sunset Key

Sunset Key’s origins are inglorious: the United States Navy built it as a fuel tank depot during the Cold War. Today it's a very different place. This privately owned island community of multimillion-dollar homes is ringed by waving palm trees, white sand, and bright blue waters accessible only via ferry. Those lucky enough to stay in one of the house rentals here can avail themselves of a swimming pool, tennis courts, spa treatments, and yoga on the beach. It would be easy to play luxury island castaway for your entire vacation, but Sunset Key is located just off the coast of the island of Key West, whose serene beaches and bustling saloons have tempted artists and writers to its shores for decades. Go island hopping to get the best of both worlds.

The best time to stay in a vacation rental in Sunset Key

There’s a reason many visitors to the Keys have made themselves permanent residents — the tropical climate is enchanting. The difference in temperature between January and July is slight. Warm, balmy days tempered by cool sea breezes are the norm. However, June through October is the wet season, marked by rain, thunderstorms, and occasional hurricanes. Look to neighboring Key West for events all year round, including Fantasy Fest in October, a weeklong party during which revelers don extravagant costumes and attend street fairs, balls, and a parade.

Top things to do in Sunset Key

Key West Museum of Art & History at the Custom House

Housed in a grand circa-1891 four-story brick building, this museum chronicles the last two centuries of art and history in Key West through two floors of exhibits. The collection includes displays devoted to notable locals and the sinking of the battleship USS Maine in Cuba’s Havana Harbor in 1898.

Key West Cemetery

The residents of Key West have as relaxed an attitude about memorials as they do about life. Dotted among the grand monuments and crypts of Key West Cemetery are cheeky tombstone messages such as “I told you I was sick” and “I’m just resting my eyes.” Established in 1847, this is an active cemetery with an estimated 100,000 people buried within. Self-guided tour maps are available at the cemetery entrance.

Fort Zachary Taylor State Park

It took 21 years to build the circa-1866 fort that lends this park its name. Used by the Union during the Civil War, and later in the Spanish-American War, the fort included then-state-of-the-art features such as a desalination plant and toilets flushed by the tide. After you’ve had your fill of history, head to the park’s gorgeous beach, where tropical fish put on a show for snorkelers. Head underwater and you may catch a glimpse of parrotfish, yellowtail snapper, lobster, and brilliant coral. Speaking of coral, there’s a lot of it at this beach, so wear water shoes (sold in the gift shop if you didn’t pack your own).

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Sunset Key