Discover Your Perfect Lower Sugarloaf Key Vacation Homes

Best Vacation Homes in Lower Sugarloaf Key

New
6 Guests 3 Bedrooms 3 Bathrooms
House
  • Air Conditioner
  • Internet
  • Laundry
R19,618/Night For 7 Nights R137,320
9.6
Exceptional
(2 Reviews)
2228.13 ft² 10 Guests 5 Bedrooms 4 Bathrooms
House
  • Pet Friendly
  • Parking
  • Air Conditioner
R4,992/Night For 7 Nights R34,946
New
1 Bedroom 1 Bathroom
Family Friendly House
  • Balcony/Terrace
  • Pet Friendly
  • Parking
R12,642/Night For 7 Nights R88,498
10.0
Exceptional
(14 Reviews)
893 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R16,346/Night For 7 Nights R114,428
9.1
Exceptional
(474 Reviews)
398.26 ft² 18 Guests 33 Bedrooms 4 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Pet Friendly
R7,521/Night For 7 Nights R52,649
10.0
Exceptional
(11 Reviews)
2239 ft² 8 Guests 2 Bedrooms 3 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R24,114/Night For 7 Nights R168,801
10.0
Exceptional
(10 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Ocean View
  • Balcony/Terrace
  • View
R4,316/Night For 7 Nights R30,216
10.0
Exceptional
(9 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Fireplace/Heating
  • Ocean View
  • Balcony/Terrace
R4,486/Night For 7 Nights R31,399

Lower Sugarloaf Key Luxury Rentals

New
1797.57 ft² 10 Guests 5 Bedrooms 4 Bathrooms
House
  • Private Beach
  • Oceanfront
  • Pool
Unlock the Best Price
New
2537 ft² 8 Guests 4 Bedrooms 4 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R90,967/Night For 7 Nights R636,777
9.8
Exceptional
(7 Reviews)
1 ft² 20 Guests 9 Bedrooms 9 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
R54,081/Night For 7 Nights R378,559
8.0
Excellent
(1 Review)
4004.17 ft² 8 Guests 1 Bedroom 4 Bathrooms
Free Cancellation House
  • Private Beach
  • Oceanfront
  • Fireplace/Heating
R46,047/Night For 7 Nights R322,330
New
4006 ft² 8 Guests 4 Bedrooms 5 Bathrooms
Group Friendly House
R39,490/Night For 7 Nights R276,431
8.0
Excellent
(2 Reviews)
2314 ft² 8 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R32,336/Night For 7 Nights R226,360
9.6
Exceptional
(11 Reviews)
678 ft² 4 Guests 2 Bedrooms 1 Bathroom
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
R31,009/Night For 7 Nights R217,065
New
14 Guests 6 Bedrooms 6 Bathrooms
Ocean View Villa
  • Oceanfront
  • Pool
  • Ocean View
R28,771/Night For 7 Nights R201,399

Lower Sugarloaf Key Pet Friendly Vacation Rentals

10.0
Exceptional
(4 Reviews)
1568 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Hot Tub
  • Fireplace/Heating
  • Pool
R9,238/Night For 7 Nights R64,670
New
904.17 ft² 4 Guests 1 Bedroom 1 Bathroom
Free Cancellation House
  • Fireplace/Heating
  • View
  • Pet Friendly
R9,519/Night For 7 Nights R66,640
10.0
Exceptional
(1 Review)
1440 ft² 6 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Fireplace/Heating
  • Pool
R5,455/Night For 7 Nights R38,181
New
1442.36 ft² 8 Guests 3 Bedrooms 2 Bathrooms
House
  • View
  • Pet Friendly
  • Parking
R7,554/Night For 7 Nights R52,879
10.0
Exceptional
(1 Review)
2 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
R2,459/Night For 7 Nights R17,210
10.0
Exceptional
(1 Review)
6 Guests 1 Bedroom 1 Bathroom
Ocean View RV Rental
  • Oceanfront
  • Pool
  • Ocean View
R2,235/Night For 7 Nights R15,650
8.4
Excellent
(7 Reviews)
1302 ft² 8 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R20,055/Night For 7 Nights R140,391
8.0
Excellent
(1 Review)
598 ft² 4 Guests 2 Bedrooms 1 Bathroom
Family Friendly House
  • Balcony/Terrace
  • Breakfast
  • Pet Friendly
R2,617/Night For 7 Nights R18,327

Lower Sugarloaf Key Large Vacation Homes

10.0
Exceptional
(9 Reviews)
12 Guests 5 Bedrooms 4 Bathrooms
Ocean View House
  • Private Pool
  • Hot Tub
  • Fireplace/Heating
R12,794/Night For 7 Nights R89,565
7.4
Very Good
(552 Reviews)
452.08 ft² 10 Guests 13 Bedrooms 3 Bathrooms
Family Friendly Cabin
  • Pool
  • View
  • Parking
R3,104/Night For 7 Nights R21,726
10.0
Exceptional
(6 Reviews)
1 ft² 10 Guests 4 Bedrooms 4 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Kitchen
R24,796/Night For 7 Nights R173,580
10.0
Exceptional
(2 Reviews)
2943 ft² 12 Guests 4 Bedrooms 4 Bathrooms
Family Friendly House
  • Private Pool
  • Pool
  • Balcony/Terrace
R8,482/Night For 7 Nights R59,382
9.8
Exceptional
(56 Reviews)
10 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • Private Pool
  • Pool
  • Balcony/Terrace
R10,022/Night For 7 Nights R70,155
9.8
Exceptional
(28 Reviews)
2142 ft² 12 Guests 5 Bedrooms 3 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Ocean View
R28,373/Night For 7 Nights R198,607
9.8
Exceptional
(14 Reviews)
2668 ft² 10 Guests 4 Bedrooms 3 Bathrooms
Family Friendly House
  • Private Pool
  • Pool
  • Balcony/Terrace
R10,480/Night For 7 Nights R73,357
9.8
Exceptional
(8 Reviews)
2450 ft² 10 Guests 5 Bedrooms 2 Bathrooms
Family Friendly House
  • Private Pool
  • Pool
  • Balcony/Terrace
R7,031/Night For 7 Nights R49,217

Why Choose Rent By Owner for your Lower Sugarloaf Key Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Lower Sugarloaf Key

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you experience the best of what this destination has to offer, whether you're seeking sunny days, pleasant weather, or fewer crowds for a more relaxed stay in the region's comfortable vacation rentals.

Peak Season Highlights

winter
Winter (December to February)

This destination experiences its peak season during the winter months when travelers seek warmer climates for their vacation rentals, enjoying mild days and cool evenings.

Average Temperature Daytime: 75°F - Nighttime: 60°F
spring
Spring Break (March to April)

Spring break brings an influx of visitors looking to enjoy pleasant weather and abundant outdoor activities, making it a vibrant time to book vacation rentals here.

Average Temperature Daytime: 78°F - Nighttime: 62°F

Off-Season Highlights

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Summer (June to August)

During these summer months, fewer travelers visit, offering a quieter experience with warm days perfect for relaxing at your vacation rental in the area.

Average Temperature Daytime: 88°F - Nighttime: 75°F
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Fall (September to November)

Autumn sees a slowdown in visitors, providing an ideal opportunity to find exclusive deals on vacation rentals while enjoying the region’s mild weather.

Average Temperature Daytime: 82°F - Nighttime: 68°F

Weekly Weather Forecast for Lower Sugarloaf Key

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

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

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 a private outdoor pool, perfect for relaxing under the Florida sun.
  • Take advantage of a spacious outdoor patio or deck for al fresco dining and entertaining.
  • Experience direct access to the waterfront with a dock or boat slip, ideal for boating enthusiasts.
  • Relax in a hammock or lounge chairs while soaking up the warm coastal breeze.
  • Utilize outdoor grilling facilities to prepare delicious meals amidst scenic surroundings.
  • Benefit from lush landscaped gardens that provide privacy and a touch of nature.
  • Make use of shaded outdoor seating areas, perfect for enjoying the region’s pleasant climate.
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Family Activities

  • Snorkeling at Looe Key Reef: Discover vibrant marine life and colorful coral formations just off the coast, making it a perfect family adventure in this tropical destination.
  • Exploring Bahia Honda State Park: Enjoy swimming, picnicking, and walking along scenic trails at this beautiful state park located nearby for outdoor family activities.
  • Wildlife Watching at the Lower Keys Marsh: Observe various bird species and other local wildlife in their natural habitat, providing an educational experience for the whole family.
  • Kayaking in the Calm Waters: Paddle through the tranquil waters of the region’s protected channels and creeks, ideal for beginners and young explorers in this family-friendly area.
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Adult Activities

  • Deep Sea Fishing Tours: Experience the thrill of deep-sea fishing in the waters surrounding this destination, renowned for its rich marine life and expert guides.
  • Snorkeling at Coral Reefs: Explore vibrant coral reefs just off the coast, offering a chance to observe colorful marine ecosystems unique to the region.
  • Paddleboarding Adventures: Enjoy serene paddleboarding sessions along the calm waters, ideal for both beginners and experienced enthusiasts looking to relax and take in the scenery.
  • Sunset Kayaking Experiences: Glide across tranquil waterways at sunset, immersing yourself in the natural beauty and peaceful environment of the area.

Other Places to Stay in Lower Sugarloaf Key, FL

Lower Sugarloaf Key Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the local waterways: Take advantage of nearby boating and kayaking opportunities to enjoy the region’s renowned aquatic scenery directly from your vacation rental.
  • Visit the best seafood spots: Indulge in fresh, local seafood at nearby eateries or prepare your own in the well-equipped kitchen of your rental to savor authentic flavors.
  • Plan outdoor activities early in the day: Make the most of the area’s pleasant mornings by engaging in activities like fishing or walking along scenic trails near your property.
  • Utilize your rental’s amenities: Relax and unwind by taking advantage of comfort features such as private pools, outdoor decks, or cozy indoor spaces tailored for a tranquil stay here.

Transportation Options

  • Private Car Rentals: You can comfortably explore the area with a private car rental, providing flexibility and convenience for your stay here.
  • Taxi Services: Reliable taxi services are available to quickly get you around the region without the hassle of driving yourself.
  • Public Transportation: Local bus routes offer an affordable way to navigate this destination, connecting you to key points of interest in the area.
  • Bicycle Rentals: For a scenic and eco-friendly option, consider renting a bicycle to enjoy the natural beauty of the region at your own pace.

Local Customs Options

  • Respect for Marine Life: Locals and visitors alike uphold a strong tradition of caring for the surrounding waters, ensuring that marine ecosystems remain healthy and vibrant.
  • Fisherman’s Respect: The region's fishing customs emphasize sustainability and appreciation for the local fish populations, which is reflected in early morning fishing practices and local cuisine.
  • Casual Coastal Attire: When visiting here, casual and beach-friendly clothing is customary, reflecting the relaxed, seaside lifestyle prevalent among residents and travelers.
  • Community Celebrations: Participating in or observing neighborhood events often involves showcasing local arts and seafood traditions, highlighting the area's rich cultural heritage.

Frequently Asked Questions About Lower Sugarloaf Key?

1. What are the top vacation rentals in Lower Sugarloaf Key?

2. How many vacation rentals have private pools in Lower Sugarloaf Key?

3. Which vacation homes in Lower Sugarloaf Key are best for families?

If you are looking for a family-friendly vacation home in Lower Sugarloaf Key, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Lower Sugarloaf Key:

4. How many Rentbyowner vacation rentals are available in Lower Sugarloaf Key?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 143 in the Lower Sugarloaf Key area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Lower Sugarloaf Key. 

5. What is the cancellation policy for vacation rentals in Lower Sugarloaf Key, Florida?

Cancellation policies vary depending on the individual property owner. It's important to review the specific listing details and contact the host directly to understand the terms before booking.

6. Are there specific rules or restrictions I should know about when booking a vacation rental here?

Each vacation rental has its own set of house rules and restrictions, such as pet policies or occupancy limits. Be sure to carefully read the listing description and reach out to the host if you have any questions.

7. How do I confirm the availability of my preferred dates in this area?

Availability is updated regularly by property owners. To ensure your dates are open, check the calendar on the listing and consider contacting the host directly for confirmation and any additional details.

8. What amenities are typically included in vacation rentals around here?

Vacation rentals in this region often feature amenities like kitchens, Wi-Fi, parking, and outdoor spaces. Review each listing carefully, as amenities can vary between properties, and contact the owner for specifics.

9. Is it necessary to contact the property owner before finalizing my booking?

While many bookings are completed through the online platform, reaching out to the owner beforehand can help clarify any questions about the property, special requests, or additional information to enhance your stay.

Lower Sugarloaf Key Top Rated Vacation Rentals

10.0
Exceptional
(6 Reviews)
1850 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
R6,272/Night For 7 Nights R43,912
10.0
Exceptional
(5 Reviews)
8 Guests 4 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Pool
R11,547/Night For 7 Nights R80,829
10.0
Exceptional
(4 Reviews)
2400 ft² 8 Guests 4 Bedrooms 3 Bathrooms
Family Friendly House
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
R6,613/Night For 7 Nights R46,293
10.0
Exceptional
(4 Reviews)
1774 ft² 8 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Private Pool
  • Pool
  • Balcony/Terrace
R6,314/Night For 7 Nights R44,191
9.6
Exceptional
(8 Reviews)
1800 ft² 10 Guests 5 Bedrooms 4 Bathrooms
Ocean View House
  • Private Pool
  • Fireplace/Heating
  • Pool
R10,613/Night For 7 Nights R74,293
9.4
Exceptional
(42 Reviews)
610.85 ft² 8 Bathrooms
Hotel
  • Private Beach
  • Oceanfront
  • Hot Tub
R2,467/Night For 7 Nights R17,276
9.4
Exceptional
(15 Reviews)
2100 ft² 8 Guests 4 Bedrooms 2 Bathrooms
Family Friendly House
  • Private Pool
  • Fireplace/Heating
  • Pool
R5,691/Night For 7 Nights R39,840
8.2
Excellent
(1001 Reviews)
1 Bathroom
Family Friendly Hotel
  • Pool
  • Balcony/Terrace
  • Parking
R3,122/Night For 7 Nights R21,858