Lower Keys Vacation Rentals

Lower Keys Florida Vacation Rentals By Owner

Start your search for oceanfront pool home rentals with docks, private pools, by owner and more below.

Cudjoe - Tranquility in Paradise (28+ night rentals)

Cudjoe Key Vacation Rentals
3/BR 2/BA SLEEPS 8

Summerland Breeze: 28 NIGHT MINIMUM! CHECK OUT OUR JUNE SPECIAL! A three-house resort style getaway in the Florida Keys

Summerland Key Vacation Rentals
7/BR 5/BA SLEEPS 14

Sunny Florida Keys Getaway

Little Torch Key Vacation Rentals
2/BR 2/BA SLEEPS 4

Little Torch Breeze

Little Torch Key Vacation Rentals
3/BR 2.5/BA SLEEPS 6

South Point Shores - Florida Keys Monthly Rental with Dock

Sugarloaf Key Vacation Rentals
3/BR 2/BA SLEEPS 6

Captain Kidd's Hideaway - Florida Keys Monthly Vacation Rental with Dock

Little Torch Key Vacation Rentals
3/BR 2/BA SLEEPS 6

Reel Paradise - Summerland Key canal front pool home

Little Torch Key Vacation Rentals
3/BR 2/BA SLEEPS 6

7 Seas

Little Torch Key Vacation Rentals
3/BR 3/BA SLEEPS 8

Bahia Azul - Private Sandy Beach - Florida Keys Monthly Vacation Rental

Ramrod Key Vacation Rentals
4/BR 2/BA SLEEPS 8

Aloe House - Affordable Cudjoe Key Monthly Rental with Dock

Cudjoe Key Vacation Rentals
3/BR 3/BA SLEEPS 6

Conch House Oceanfront Home With Amazing Panoramic Views

Little Torch Key Vacation Rentals
4/BR 4/BA SLEEPS 7

Margarita Villa - Little Torch Key Monthly Rental with Dock

Little Torch Key Vacation Rentals
3/BR 2/BA SLEEPS 6

Buccaneer Boathouse - Florida Keys Monthly Rental

Little Torch Key Vacation Rentals
2/BR 2/BA SLEEPS 4

Summerland Nest - Oceanfront with pool

Summerland Key Vacation Rentals
7/BR 5/BA SLEEPS 12

KEYS TO THE TROPICS

Big Pine Key Vacation Rentals
3/BR 2/BA SLEEPS 8

Sunkissed - Florida Keys Monthly Rental

Ramrod Key Vacation Rentals
2/BR 1.5/BA SLEEPS 4

Oasis -Oceanfront tropical home with pool and dock

Summerland Key Vacation Rentals
4/BR 3/BA SLEEPS 14

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Lower Keys Vacation Rentals

The Lower Keys are a chain of tropical islands located in the southernmost part of the Florida Keys. These islands, including Big Pine Key and Marathon, are known for their crystal clear waters, beautiful beaches, and unique wildlife. The Lower Keys are the perfect destination for couples, families, and nature enthusiasts looking to relax and unwind in a peaceful and serene setting.

Hosts in the Lower Keys often rent their homes for a minimum of 30 nights, with check-ins typically on the first of the calendar month. Keep reading for more information to help with your search.

Is the Lower Keys a good place to rent a vacation rental?

The Lower Keys offer a wide variety of vacation rentals to choose from, including beachfront homes, condos with private docks, and pool homes. Whether you're looking for a romantic getaway or a family vacation, the Lower Keys have something for everyone. With its beautiful homes and unique amenities, the Lower Keys are one of the best places in Florida to rent a vacation home.

What do I need to know to rent a vacation home in the Lower Keys?

Lower Keys Vacation Rental Information

The Lower Keys have their own rules and regulations for vacation rentals. With a limited number of small hotels and motels in this area, vacation rentals are the primary accommodation option in the Lower Keys.

Typical Stay Periods

Vacation rentals in the Lower Keys can be rented for different periods of time, depending on the host's preference and the location of the property. Most hosts in the Lower Keys rent their homes on a monthly basis.

  • monthly
Typical Rental Turnover Day

The typical rental turnover day for the majority of the homes in Florida Keys is the first and last day of the calendar month. This makes this area perfect for snowbirds, seasonal renters and digital nomads to find their perfect home away from home for longer stays.

How much does it cost to rent a vacation home in the Lower Keys?

Lower Keys Vacation Rental Price Information

The cost of vacation rentals in the Lower Keys can vary greatly depending on the time of year and the size/location of the property. Generally speaking, peak season (December-April) will be the most expensive time to visit, while shoulder seasons (May-November) offer more moderate pricing.

  • Low range: $94 per night - $660 per week - $3,000 per month
  • High range: $715 per night - $5,005 per week - $20,020 per month

Rental Booking Window - Lower Keys

The Lower Keys are a popular vacation destination, so it's a good idea to book your vacation rental well in advance. On average, the booking window for this region is 5-6 months ahead of time. To secure your favorite property, it's best to plan ahead.

However, if you're flexible with your travel dates, you might find great last-minute deals on vacation rentals that haven't book yet. But if you're set on specific dates, it's best to book early.

Guest Retention

Many visitors to the Lower Keys fall in love with the area and return with their families year after year, which increases the demand for vacation rentals. Being one of the best diving, snorkeling and fishing locations in the entire United States it's a mecca to return to again and again.

High Season

High Season - December to April

High season in the Lower Keys runs from December through April, including all major holidays. During this time, it is common for the Keys to book up to 100% occupancy. If you'd like to visit during high season it is best to book as early as possible.

Prices are generally highest during the peak season from December through the first or second week of April, when larger homes can cost over $800 per night.

Low Season - Summer and Fall

The "low season" for vacation rentals in the Lower Keys of Florida typically refers to the period of time with the least amount of tourism, and therefore the lowest demand and lowest prices for vacation rentals. In the Lower Keys, the low season is usually during the summer months, as well as the early fall. During this time, you may be able to find discounted rates on vacation rentals, as well as fewer crowds and shorter lines at local attractions. However, it is important to note that weather in the Lower Keys can be quite hot and humid during the summer, with the risk of hurricanes increasing in the fall. If you are considering a vacation rental in the Lower Keys during the low season, it is a good idea to check the weather forecast and be prepared for potentially challenging conditions. Buying travel insurance is a good option to protect your vacation investment.

When should Snowbirds book Monthly Stays in the Lower Keys?

Lower Keys Monthly Vacation Stays

The best time of year for a senior or digital nomad to book a monthly vacation rental in the Lower Keys of Florida will depend on their personal preferences and the types of activities they are interested in. If you are looking for the most pleasant weather and the lowest prices, you may want to consider booking a rental during the low season, which is usually during the summer and early fall. However, keep in mind that the Lower Keys can be quite hot and humid during this time, with the risk of hurricanes increasing in the fall.

If you are more interested in experiencing the local culture and amenities, you may want to consider visiting during the high season, which is typically during the winter months. During this time, you can expect more crowds and higher prices, but you will also have access to a wider range of activities, such as festivals and events, as well as more opportunities to interact with other tourists and locals.

Ultimately, the best time for a senior or digital nomad to book a monthly vacation rental in the Lower Keys will depend on their personal priorities and what they hope to get out of their trip.

How do I book a pet friendly vacation rental in the Lower Keys of Florida?

Lower Keys Pet Friendly Rentals

There are a number of dog parks in the Lower Keys of Florida where you and your furry friend can enjoy some quality time together.

One popular dog park in the Lower Keys is the Key West Dog Park, located at the intersection of Frances Street and Southard Street in Key West. This fully-fenced dog park features separate areas for small and large dogs, as well as plenty of shade and water stations to keep your pooch cool and hydrated. The Key West Dog Park also has a playground and picnic tables, making it a great spot for the whole family to spend some time together.

Another option is the Marathon Bark Park, located at the Marathon Community Park on Sombrero Beach Road. This dog park features separate areas for small and large dogs, as well as plenty of room to run and play. The Marathon Bark Park also has a shaded seating area, so you can sit and watch your dog have fun while you take a break.

If you're looking for a more secluded spot to enjoy with your dog, you might also consider visiting one of the many beaches in the Lower Keys that allow dogs. Some of the best options include Higgs Beach in Key West and Sombrero Beach in Marathon. Just be sure to check the local ordinances before you go, as some beaches have specific rules about where dogs are allowed.

Overall, the Lower Keys offer a variety of dog-friendly parks and beaches where you and your furry friend can enjoy the beautiful Florida weather and have some fun together.

Where can I find information about Lower Keys Vacation Rentals?

Vacation Rental Statistics

Use the search filters on Florida Rental By Owners website to look for accommodations meeting your criteria.

Lower Keys Vacation Rentals with Pool and Hot Tubs

The Florida Lower Keys are ideal for outdoor living while on vacation. There are multiple options for pools, and hot tubs which make this an ideal year-round destination.

Lower Keys Rental Property Types

There are an abundance of vacation rental accommodation types, the majority ranging from condos to private canal homes: 

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