Sugarloaf Key vacation rentals

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Discover a selection of 51 homes and other vacation rentals in Sugarloaf Key that are perfect for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a pool. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.
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Find out more about Sugarloaf Key

Find out more about Sugarloaf Key

Why visit Sugarloaf Key

  1. Outdoor Adventures: Enjoy a variety of outdoor activities, from fishing charters to kayaking in the beautiful waters of Sugarloaf Key.
  2. Beautiful Beaches: Relax on stunning beaches, perfect for sunbathing and swimming in the crystal-clear waters.
  3. Family-Friendly Activities: Experience a range of family-oriented experiences, ensuring fun for all ages.
  4. Rich Culture: Explore local attractions, including historic houses and nearby islands that showcase the area's vibrant culture.
  5. Variety of Accommodations: Choose from cozy condos, charming homes, and delightful cottages for a perfect stay.

Popular types of accommodation around Sugarloaf Key

Planning your getaway to Sugarloaf Key? Discover the perfect vacation rental to suit your needs! From charming waterfront cottages to spacious private homes and luxurious condos, there’s something for everyone. Enjoy a relaxing stay at Sugarloaf Lodge or unwind in a resort home with a pool. Experience the beauty of Sugarloaf Key, where comfort and adventure await!

  • Condos: The top choice for visitors to Sugarloaf Key, offering modern amenities and beautiful views.
  • Cottages: A delightful option for those seeking a quaint and cozy experience among tropical surroundings.
  • Houses: Ideal for families or groups, these homes provide space and comfort for a relaxing getaway.
  • Apartments: A convenient choice for travelers looking for a home-like atmosphere with easy access to local attractions.
  • House Boats: Experience a unique stay on the water with charming and adventurous houseboat rentals.**

Top attractions around Sugarloaf Key

Sugarloaf Key offers a perfect blend of outdoor activities, beautiful beaches, and family-friendly experiences. Visitors can explore local attractions such as historic houses and stunning islands, while also enjoying the area's rich culture. Fishing charters are a popular option for those looking to experience the waters. Whether you're traveling solo or with family, Sugarloaf Key promises a memorable vacation filled with adventure and relaxation.

  1. Florida Keys Beaches: Located just 1 mile from Sugarloaf Key, this beautiful beach offers a relaxed atmosphere with stunning ocean views, perfect for sunbathing, swimming, and enjoying beach vibes.
  2. Duval Street: Approximately 17 miles away, Duval Street is a lively area known for its vibrant nightlife, unique shops, and diverse dining options, embodying the energetic city vibes of Key West.
  3. Upper Sugarloaf Key: Nestled within Sugarloaf Key, this charming neighborhood features a local community vibe, with quaint homes and access to outdoor activities, making it a great spot to explore.

Things to do recommended for families

Families can have a splashing good time at the MLK Community Pool & Community Center, located 17 miles from Sugarloaf Key. With its family-friendly atmosphere and sports activities, it’s a great spot for outdoor fun and relaxation for all ages.

Things to do recommended for groups

Group travelers to Sugarloaf Key can enjoy a round at the nearby Key West Golf Club, discover unique finds at the Big Pine Key Flea Market, and experience a captivating show at the Key West Burlesque Theater for a perfect blend of outdoor fun, local shopping, and entertainment.

What do I need to keep in mind when booking a vacation around Sugarloaf Key

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Sugarloaf Key with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group activities. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Sugarloaf Key with young kids: Traveling with young children can present its difficulties. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Sugarloaf Key: For many families, a vacation wouldn’t feel complete without their beloved furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Sugarloaf Key: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the perfect spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Sugarloaf Key

Sugarloaf Key offers an idyllic vacation experience perfect for families and outdoor enthusiasts alike. Nestled within the stunning Florida Keys, this tropical paradise allows visitors to explore nearby Summerland Key, where adventure and relaxation await. With a blend of budget-friendly excursions and family-friendly activities, you can soak in the vibrant atmosphere filled with history and romance. Whether you're seeking beach days or thrilling adventures, Sugarloaf Key is the perfect destination for unforgettable memories.

  • Key West: Located 17 miles from Sugarloaf Key, Key West is renowned for its vibrant atmosphere and rich history. This lively city attracts travelers seeking a mix of family fun, business opportunities, and urban experiences. Explore the bustling shopping areas, indulge in local cuisine at charming restaurants, or relax on the family-friendly beaches. Don’t miss iconic landmarks like the Southernmost Point Buoy and the Ernest Hemingway Home and Museum, which offer a glimpse into the island’s unique culture and heritage.
  • Sugarloaf Shores: Nestled around Sugarloaf Key, Sugarloaf Shores is a serene neighborhood perfect for those looking for outdoor adventures and family-friendly experiences. Visitors can enjoy the beautiful beaches and recreational areas, making it an ideal spot for swimming, snorkeling, or simply soaking up the sun. With its proximity to shopping centers and local attractions, Sugarloaf Shores offers a laid-back atmosphere while still providing access to everything you need for a memorable vacation.
  • Bay Point: Just 3 miles from Sugarloaf Key, Bay Point is a charming city that embodies the essence of the Florida Keys. With its focus on outdoor activities and family experiences, Bay Point is perfect for those who love nature and water sports. Enjoy easy access to stunning beaches, explore the nearby archipelago, or visit the local shopping areas for unique finds. Bay Point is an excellent base for adventure seekers and families alike, offering a welcoming community feel and a picturesque setting.

Best time to go to Sugarloaf Key, Summerland Key

If you're planning a trip to Sugarloaf Key, Summerland Key, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March to April and September, while off-peak times, like August and October to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January71.1°F (21.7°C)No Rain (Dry)Mostly SunnyAverageAverage
February72.1°F (22.3°C)No Rain (Dry)Mostly SunnyAverageAverage
March73.2°F (22.9°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
April76.8°F (24.9°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageAverage
July84.0°F (28.9°C)Light RainMostly SunnyAverageAverage
August84.4°F (29.1°C)Light RainMostly SunnyModerately LowSlightly Low
September83.7°F (28.7°C)Light RainMostly SunnyModerately HighSlightly Low
October80.8°F (27.1°C)Light RainMostly SunnyModerately LowSlightly Low
November76.6°F (24.8°C)Light RainMostly SunnyModerately LowAverage
December73.8°F (23.2°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that meets your budget, simply use our filters to narrow down options by price, location, and type of vacation rental. We're here to help you find the perfect fit for your getaway!

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner has its perks! When you join our travel rewards program, One Key, you can immediately access member discounts and earn OneKeyCash™ on eligible reservations. Enroll today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new trips, manage your existing arrangements, or review your reservations. You can easily find your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

For vacations as sweet as sugar, head to Sugarloaf Key

Sunshine and palm-lined sandy beaches, life in the Florida Keys doesn't get better than this. Sugarloaf Key is a real highlight of the famed Florida Keys. Book a Sugarloaf Key vacation rental in the heart of the island and have some of the best beaches right on your sandy doorstep. Kayaking, swimming and snorkeling are all popular activities. Try a skydiving experience from the small airport, or book a day trip to the Great White Heron National Wildlife Refuge. But if it's just a chilled out vacation you need, then Sugarloaf Key has timeless relaxation written all over it.

For uber scuba diving, visit Sugarloaf Key

The Florida Keys are one of the state's most popular diving spots. Located 5 miles offshore from Big Pine Key is the Looe Key National Marine Sanctuary. A popular scuba diving and snorkeling spot, it has the sunken Adolphus Busch shipwreck, which is home to sharks, parrotfish, and barracuda. From your Sugarloaf Key vacation rental, book a scuba diving or snorkeling safari. Back on dry land, don't miss the Bat Tower, one of 14 (now defunct) wooden towers built in 1929 to attract bats to the Keys.

The Keys to Success - Florida at its best

Life on Sugarloaf Key is all about the beach. Soft coral-white sands lined with swaying palm trees is best for lounging around on with a cocktail in hand. One of the most popular beaches is Sugarloaf Beach on the south of the island. While many come to relax under a radiant sun, there's plenty to keep the water enthusiast occupied. Book a guided sea kayaking tour through the Florida Keys' mangroves, a dolphin-spotting cruise, or a snorkeling safari to see shoals of rainbow-colored fish as they swim just beneath the surface.

Summertime Blues on Sugarloaf Key

Endless sunshine and blue skies, Sugarloaf Key has certainly been blessed by the weather gods. The Florida Keys' rainy season falls between June and September, when the chance of daily showers increases. The busiest time to visit is spring, between February and May, when the sun is almost always shining and temperatures reach highs of 90 degrees. For the best choice of Sugarloaf Key vacation rentals, come in fall, but beware of high winds as it's the height of hurricane season.

Exploring the natural landscape of Sugarloaf Key

Whether you're an active traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Sugarloaf Key. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Florida Keys Beaches (1.5 mi / 2.4 km)
  • Boca Chica Nude Beach (9.7 mi / 15.7 km)
  • Key West Tropical Forest and Botanical Garden (13.4 mi / 21.6 km)
  • Smathers Beach (15.4 mi / 24.8 km)
  • Higgs Beach (16.1 mi / 26 km)
  • Calusa Beach (16.7 mi / 26.9 km)

How to get to and around Sugarloaf Key

The nearest airport is in Key West Intl. Airport (EYW), located 14.2 mi (22.8 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Marathon, FL (MTH-Florida Keys Marathon), which is 31.6 mi (50.9 km) away.

Frequently asked questions

How much does it cost to rent a vacation rental in Sugarloaf Key?
Length of stay, property type and season are some of the conditions that can affect the price of a vacation home. Simply add your travel dates to find your perfect fit. From comfy cottages to sprawling luxury villas, all Vrbo vacation rentals offer unbeatable value.
How much does it cost to rent a beach house in Sugarloaf Key?
The average price for a vacation rental near the beach in Sugarloaf Key depends on when you’ll be there and the size and type of property you’re looking for. You can easily and quickly find prices on Vrbo by entering your destination and preferred travel dates. Then use the handy filter tool to select the number of bedrooms and amenities that you need, like WiFi, a pool and air conditioning.
How old do you have to be to rent a vacation rental in Sugarloaf Key?
We recommend checking with the Sugarloaf Key vacation property you’re looking at on Vrbo as the minimum age varies. However, it’s normally 16, 18 or 21.
How long can I rent a vacation rental in Sugarloaf Key for?
The amount of time you can stay in a Sugarloaf Key vacation home for varies depending on the property. Simply put in your travel dates to browse options offering longer term stays. They have all you require to make your extended trip more enjoyable and comfortable, such as air conditioning and laundries. Some vacation homes may also offer weekly or monthly discounted prices, so you can stay longer for less money.
Does Vrbo offer discounts for vacation homes in Sugarloaf Key?
On Vrbo, you’ll find amazing deals and discounts for Sugarloaf Key. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re off on a short getaway or a longer stay, Vrbo offers lots of options for all styles and budgets.

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