Sugarloaf Key Accommodations

3-bedroom Ocean-front house in Sugarloaf Key with large private swim/boat dock!

New Property

New

3-bedroom Ocean-front house in Sugarloaf Key with large private swim/boat dock!

6 Guests 3 Bedrooms 3 Bathrooms

House

Air Conditioner
Internet
Laundry

AU $1,678/Night For 7 Nights AU $11,746

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9.6

Exceptional

(2 Reviews)

Pelico Paradise

2228.13 ft² 10 Guests 5 Bedrooms 4 Bathrooms

House

Pet Friendly
Parking
Air Conditioner

AU $427/Night For 7 Nights AU $2,989

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New

Starlight Serenity - Hideaway w Stunning Views

1 Bedroom 1 Bathroom

Family Friendly House

Balcony/Terrace
Pet Friendly
Parking

AU $1,081/Night For 7 Nights AU $7,570

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Private and Exclusive Florida Keys Getaway

10.0

Exceptional

(14 Reviews)

Private and Exclusive Florida Keys Getaway

893 ft² 4 Guests 2 Bedrooms 2 Bathrooms

Ocean View House

Oceanfront
Fireplace/Heating
Ocean View

AU $1,398/Night For 7 Nights AU $9,788

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Highly Rated

9.1

Exceptional

(474 Reviews)

Sugarloaf Key RV Resort & Cottages

398.26 ft² 18 Guests 33 Bedrooms 4 Bathrooms

Family Friendly House

Fireplace/Heating
Pool
Pet Friendly

AU $643/Night For 7 Nights AU $4,503

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10.0

Exceptional

(11 Reviews)

Private and Exclusive Beach Getaway

2239 ft² 8 Guests 2 Bedrooms 3 Bathrooms

Ocean View House

Oceanfront
Fireplace/Heating
Ocean View

AU $2,063/Night For 7 Nights AU $14,438

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8.0

Excellent

(1 Review)

Villa of the Setting Sun

4004.17 ft² 8 Guests 1 Bedroom 4 Bathrooms

Free Cancellation House

Private Beach
Oceanfront
Fireplace/Heating

AU $3,939/Night For 7 Nights AU $27,570

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Tropical paradise on canal in Lower Keys-pool, tiki, firepit, dock, dog friendly

10.0

Exceptional

(1 Review)

Tropical paradise on canal in Lower Keys-pool, tiki, firepit, dock, dog friendly

1440 ft² 6 Guests 2 Bedrooms 2 Bathrooms

Ocean View House

Private Pool
Fireplace/Heating
Pool

AU $467/Night For 7 Nights AU $3,266

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7.4

Very Good

(552 Reviews)

Sugarloaf Lodge

452.08 ft² 10 Guests 13 Bedrooms 3 Bathrooms

Family Friendly Cabin

Pool
View
Parking

AU $265/Night For 7 Nights AU $1,858

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Spacious Pull-Through RV Lot at Sugarloaf Key with Pool, Saltwater Lake Access & Tiki Bar

Price Dropped

10.0

Exceptional

(1 Review)

Spacious Pull-Through RV Lot at Sugarloaf Key with Pool, Saltwater Lake Access & Tiki Bar

6 Guests 1 Bedroom 1 Bathroom

Ocean View RV Rental

Oceanfront
Pool
Ocean View

AU $191/Night For 7 Nights AU $1,339

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New

Starlight Serenity - Hideaway with Stunning Views

904.17 ft² 4 Guests 1 Bedroom 1 Bathroom

Free Cancellation House

Fireplace/Heating
View
Pet Friendly

AU $814/Night For 7 Nights AU $5,700

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9.6

Exceptional

(11 Reviews)

The Lighthouse - Beach Houses Key West

678 ft² 4 Guests 2 Bedrooms 1 Bathroom

Ocean View House

Oceanfront
Fireplace/Heating
Pool

AU $2,652/Night For 7 Nights AU $18,567

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More Top-Rated Accommodations in Sugarloaf Key Area

Why Choose Rent By Owner for your Sugarloaf Key Accommodations?

What makes our Accommodations special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Sugarloaf Key Accommodations

Where are the best neighborhoods to stay in Sugarloaf Key?

In Sugarloaf Key, Florida, you’ll find neighborhoods that offer a perfect blend of tranquility and easy access to the area's natural beauty. Whether you prefer staying in a quiet, residential area or closer to the waterfront, each neighborhood provides a unique experience suited to your relaxed island getaway. Explore the local charm and enjoy seamless booking options for your ideal stay in this inviting part of Florida.

Sugarloaf Shores

In this area, you can enjoy a peaceful retreat while being close to the natural beauty that surrounds Sugarloaf Key. It offers a selection of reliable accommodations perfect for those seeking a serene stay in the region, ensuring a comfortable and seamless experience.

View 141+ Rentals in Sugarloaf Shores

Best Times to Visit Sugarloaf Key

When should you plan your Accommodations stay?

Choosing the optimal time to vacation here can enhance your experience, as the region offers ideal conditions for relaxation and outdoor activities during specific seasons, allowing you to enjoy the best of this destination's natural beauty and warm climate.

Peak Season Highlights

December to April

During this period, the area experiences its peak season as visitors seek warm weather and pleasant beach conditions. This is an ideal time to enjoy outdoor activities while escaping colder climates elsewhere.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 65°F to 70°F

June to August

The summer months bring the high season with lively atmosphere and longer days, perfect for water-based pursuits and exploring the region’s natural beauty.

Average Temperature Daytime: 88°F to 92°F - Nighttime: 78°F to 82°F

Off-Season Highlights

May and November

Shoulder months offer a quieter experience with fewer crowds, making it a great choice for travelers seeking more relaxed accommodations and outdoor serenity.

Average Temperature Daytime: 77°F to 85°F - Nighttime: 68°F to 74°F

September and October

Early fall can be less crowded, though it's wise to consider potential weather changes. It provides a peaceful setting for a more private getaway.

Average Temperature Daytime: 82°F to 87°F - Nighttime: 73°F to 78°F

Weekly Weather Forecast for Sugarloaf Key

How to Book Your Sugarloaf Key Accommodations

What's our booking process?

Our platform allows you to browse a curated selection of accommodations. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Sugarloaf Key

More Top-Rated Accommodations in Sugarloaf Key Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

Enjoy outdoor cooking with a private barbecue grill in your vacation rental’s backyard.
Relax and sunbathe on spacious decks or patios overlooking the water.
Take advantage of outdoor dining areas perfect for al fresco meals.
Make use of docks or boat slips if your accommodation offers waterfront access.
Swim in a private pool to cool off after exploring the scenic region.
Benefit from lush landscaped gardens that add to the outdoor ambiance of your stay.
Utilize dedicated outdoor lounge spaces for relaxing evenings under the stars.

Top Attractions Around Sugarloaf Key

What attractions are nearby?

In this vibrant destination, you can enjoy a variety of outdoor activities such as fishing, kayaking, and snorkeling just moments from your stay, offering an authentic experience of the region's natural beauty and marine life.

Family Activities

Snorkeling and Beach Exploration: Discover the vibrant marine life and pristine beaches that make this region ideal for family snorkeling adventures, offering memorable experiences right at your doorstep.
Kayaking and Water Activities: Enjoy peaceful kayaking excursions in the calm waters surrounding this destination, perfect for families seeking outdoor fun and scenic views.
Wildlife Viewing and Nature Tours: Explore local parks and nature reserves where you can observe native wildlife and learn about the area's unique ecosystems with your loved ones.
Family-Friendly Boat Tours: Embark on guided boat tours that showcase the stunning scenery and rich marine environment, providing engaging activities for all ages here in the region.

Adult Activities

Deep-sea Fishing: Experience the thrill of deep-sea fishing excursions, where you can catch a variety of local game fish in the pristine waters surrounding this destination.
Snorkeling and Diving: Explore vibrant coral reefs and marine life through snorkeling and diving adventures that showcase the area's rich underwater ecosystems.
Kayaking and Paddleboarding: Enjoy tranquil paddling sessions along calm waterways, ideal for observing the natural beauty and wildlife of the region.
Sunset Cruises: Relax aboard a sunset cruise to witness breathtaking views over the water, making for an unforgettable evening in this scenic locale.

Other Places to Stay in Sugarloaf Key, FL

Lower Florida Keys

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Upper Sugarloaf Key

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Key West Fly Fishing

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Sugarloaf Shores

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Lower Sugarloaf Key

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Sugarloaf Beach

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Upper Sugarloaf Sound

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More Places to Stay Near Sugarloaf Key

Sugarloaf Key Travel Tips

How Can You Make the Most of Your Stay?

Plan your activities early: Explore the region's renowned outdoor recreation options to make the most of your stay in Sugarloaf Key and ensure availability for popular excursions.
Choose waterfront accommodations: Opt for properties with direct access to the water to enjoy the scenic beauty and tranquility that define this destination's atmosphere.
Respect the local environment: Practice eco-friendly habits during your visit to help preserve the pristine natural surroundings that make the area so unique.
Utilize local resources: Take advantage of nearby shops, dining, and services to immerse yourself fully in the region's lifestyle while supporting the local community.

Transportation Options

Rental Car Services: Renting a vehicle gives you the flexibility to explore this destination and its surrounding areas at your own pace, ideal for those staying in Sugarloaf Key.
Public Transportation: Local buses provide an affordable and convenient way to navigate the region without the hassle of parking or driving.
Shuttle Services: Specialized shuttles operate between key locations in the area, making it easy to reach popular spots and transport accommodations.
Taxis and Rideshare Options: Taxis and rideshare services like Uber or Lyft offer quick, reliable transportation around the destination for your convenience.

Local Customs Options

Respect for the Seafood Industry: Locals in this destination often have a deep appreciation for their seafood traditions, so visitors are encouraged to honor local fishing practices and cuisine.
Environmental Preservation Etiquette: The area values its natural beauty, making it customary to participate in conservation efforts, such as avoiding littering and respecting protected wildlife habitats.
Waterway Courtesy: Navigating the region’s water channels involves observing boating right-of-way rules and maintaining a respectful distance from other vessels and swimmers.
Community Festivities: Participating in or observing local celebrations and seasonal events is common, and engaging with these customs offers a genuine experience of regional culture.

Frequently Asked Questions about Sugarloaf Key Accommodations

1. What are the top Accommodations in Sugarloaf Key?

There are a lot of options in Sugarloaf Key. If you plan on staying in the Sugarloaf Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Accommodations in Sugarloaf Key:

2. How many Accommodations are available in Sugarloaf Key?

Currently, the total number of properties listed by RBO in 2026 is over 95 in the Sugarloaf Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Sugarloaf Key. 

3. What is the cancellation policy for accommodations in this destination?

The cancellation policy varies depending on the property owner and listing. It is recommended to review the specific cancellation and refund terms detailed on the property listing before booking.

4. Are there options for early check-in or late check-out available?

Early check-in and late check-out requests are subject to availability and approval by the property owner. You should contact the host directly through the listing to inquire about these options.

5. How do I find out about amenities included with my stay?

Details about amenities are provided in each property listing. For any specific questions, you can reach out to the property owner directly for clarification before confirming your reservation.

6. What are the payment methods accepted for booking here?

Payment methods are specified on the listing page and typically include major credit cards and other secure online payment options. For additional assistance, you can contact the property owner or support.

7. Is there a minimum stay requirement for bookings in this area?

Minimum stay requirements depend on the property listing and can vary. Make sure to check the reservation details on the listing page to confirm the length of stay permitted.