Short Term Rental Management in Key West, Florida

Short Term Rental Management in Key West

Awning offers full-service vacation rental property management for busy vacation rental owners and Airbnb hosts in Key West, Florida. Starts at 15% of revenue.

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Key West, Florida

Key West, Florida is a popular destination for tourists seeking a tropical vacation. The area is known for its beautiful beaches, warm weather, and variety of water activities such as fishing and boating. It also offers a lively nightlife, delicious seafood, and a rich history and culture. This makes it an attractive location for Airbnb rentals, as visitors often come to the area to soak up the sun, enjoy the laid-back island lifestyle and explore the many things to do and see in Key West.

The seasonality for Airbnb stays and tourism in Key West is heavily influenced by the winter months. From December to April, the town is bustling with visitors and bookings are at their highest. The summer months also see a decent amount of visitors, but not as many as the winter months. The shoulder seasons of fall and spring tend to be the least busy.

Key West has specific short-term rental regulations in place, including a requirement for hosts to register their property with the town and obtain a rental permit. There are also restrictions on the number of guests that can stay in a rental property and the maximum number of days a property can be rented out per year. As an Airbnb host, it is important to be aware of and comply with these regulations to avoid fines or penalties.

Managing an Airbnb in Key West can be challenging for hosts, particularly when it comes to ensuring compliance with local regulations and maintaining the property. A professional Airbnb management company can help by handling all aspects of property management, such as cleaning, maintenance, and guest communication. They can also provide support and guidance on complying with local regulations and maximizing bookings.

In Key West, the most sought-after amenities and locations for Airbnb rentals are properties with ocean views, access to the beach and proximity to popular tourist attractions such as the Ernest Hemingway Home and Museum, the Harry S. Truman Little White House and the Southernmost Point Buoy. Properties that are well-maintained and have modern amenities such as air conditioning, high-speed internet, and comfortable furnishings are also in high demand.

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Market overview
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Airbnb seasonality
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Short-term rental regulations
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Airbnb property management
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Locations and amenities
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Key West, Florida

Key West’s short-term rental market remains one of the nation’s most lucrative. Listings average a 72% occupancy rate, $347–$371 ADR, and approximately $7,900–$7,600 monthly income. Market trends show a strong demand for entire-home condos and 2-bedroom units, often attracting couples and small groups, with 1–3 bedroom homes capturing the majority of bookings. High-end, fully renovated properties with vacation-style amenities—like pools, outdoor kitchens, and flexible one-night minimums—are especially successful.

Rental Seasonality

The seasonality for Airbnb stays and tourism in Key West is heavily influenced by the winter months. From December to April, the town is bustling with visitors and bookings are at their highest. The summer months also see a decent amount of visitors, but not as many as the winter months. The shoulder seasons of fall and spring tend to be the least busy.

Top Neighborhoods & Attractions

Key West is known for its vibrant Old Town district, home to charming historic architecture, Duval Street's nightlife, and eclectic dining. Visitors flock to attractions like Mallory Square’s Sunset Celebration, Ernest Hemingway's Home and Museum, and the Key West Butterfly & Nature Conservatory. The Southernmost Point buoy and Fort Zachary Taylor Historic State Park are also top destinations.

Average Daily Rate

$503

Average Occupancy Rate

66%

Property Management Fees

25% to 35%

Average Annual Revenue

$101.8k | up 8% year over year

Taxes & Regulations in Key West, Florida

Short Term Rental Regulations

Short‑term rentals (under 30 days) are allowed but tightly regulated. Hosts must obtain a City of Key West Business Tax Receipt plus a Monroe County Transient Occupancy Rental (TOR) license for rentals under six months. A minimum stay of 28 nights is required, and zoning rules may further restrict eligible properties.

Taxes

Owners must collect and remit a 5% Tourist Development Tax, 7.5% State Sales Tax, and a 1.5% County Discretionary Sales Surtax on rental income.

Ease of Regulation

Difficult | Strict zoning laws, minimum stay requirements, and additional permits make compliance challenging.

Types of Short Term Rental Properties in Key West, Florida

Key West offers an extraordinary diversity of Airbnb accommodations that capture the island's unique maritime character and tropical charm. Visitors can choose from waterfront houseboats and boats for an authentic Keys experience, historic cottages and bungalows that reflect the city's Victorian architecture, or luxurious villas and condos with modern amenities. The destination features everything from budget-friendly camping options and tiny homes to upscale boutique hotels and serviced apartments. Unique accommodations include treehouses, castles, and even a tent option for adventurous travelers. Traditional options like entire homes, townhouses, and rental units provide comfortable stays, while specialty lodging such as bed and breakfasts, resorts, and aparthotels cater to different preferences and budgets. In terms of amenities, 74% of properties have a pool, 25% have a hot tub and 70% have a washer and dryer.

Bedrooms
Average daily rate
1 bed

$348

2 bed

$521

3 bed

$742

4+ bed

$1547

Why choose Awning

We have an experienced team and a suite of technology dedicated to providing the best service possible.

Awning logo
Other property managers
Cost
Starting at 15%
25-40%
Host communications
Dedicated phone and text line with no time on hold
Chat bots, hold lines and email threads
Insurance
Robust liability and dwelling coverage for every reservation
Spotty coverage with low claim approval rates
Contract
Pricing
Communication
Management
Maintenance
Reporting
Value

No cancellation fees
No contract lock-in
Just 90 days notice to cancel

Annual contracts with cancellation penalties

Awning logo
Other
Cost
Starts at 5%
25-40%
Host communications
Dedicated phone and text line with no time on hold
Chat bots, hold lines and email threads
Insurance
Robust liability and dwelling coverage for every reservation
Spotty coverage with low claim approval rates
Average guest rating

No cancellation fees
No contract lock-in
Just 90 days notice to cancel

Annual contracts with cancellation penalties

Experience in numbers

Rest well knowing your property is managed by an experienced team powered by world-class technology.

+10-30%

in gross revenue

4.8 stars

guest rating

5+ years

managing STRs

What you get with Awning in Key West, Florida

Taking care of your home

Awning’s team ensures your home is maintained and stocked well and always ready for its next booking.

Making guests happy

With an always available operations and support team, we’re available to take the 2am call about the toilet to make your guest happy.

Attract the most guests

We use our data and best practices to ensure your listing performs as well as possible and makes you the most money.

Unlock your home’s potential

Schedule a call to learn more about Awning’s Short Term Rental Property Management Service.

Schedule a call
Call or text 415-223-2830

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FAQ

What is vacation rental management?

Vacation rental management is the full operation of a short-term rental property, including listing optimization, booking coordination, guest communication, cleaning, and maintenance to maximize revenue and satisfaction. It’s ideal for owners who want a hands-off income stream. Learn how it works with Awning’s vacation rental management services.

How does Airbnb management work?

Airbnb management covers optimizing your listing, managing bookings and calendars, messaging guests, coordinating cleaning and repairs, and adjusting pricing to drive revenue. A professional manager handles these tasks so owners can stay passive.

What are the benefits of hiring a professional Airbnb manager?

Professional Airbnb managers handle everything from guest inquiries and pricing to maintenance and compliance, resulting in higher efficiency, more consistent occupancy, and better reviews—even while you focus on other priorities. Explore more at Awning’s owner resources.

What is full-service vs half-service vacation rental management?

Full-service management covers everything from listing creation and pricing to guest support, cleaning, and maintenance. Half-service plans handle fewer operational tasks, often leaving cleaning and guest messaging to the owner. See full-service benefits.

Are there restrictions on personal use for properties under Awning management?

Owners can block dates on the calendar for personal use as long as it doesn’t conflict with existing bookings. Discuss your calendar preferences directly with your Awning advisor. Start with Awning contact & advisor scheduling.

How much are Awning property management fees?

Awning’s full-service vacation rental management fees start at 10% of monthly revenue, depending on property type, location, and services needed. This competitive pricing includes core management but may vary with additional offerings. See the full breakdown at Airbnb management fees explained.

What services does Awning vacation rental management offer?

Awning handles all key short-term rental management services, including:

  • Listing optimization & marketing
  • Dynamic pricing models
  • Guest communication & calendar management
  • Cleaning, linen, and restocking
  • Pool, hot tub & lawn maintenance
  • Smart home automation & guidebooks

Explore the full services list at Awning vacation rental management services.

Can Awning help me convert a rental property or home into an Airbnb?

Yes — Awning assists owners from property selection and furnishing to final setup and ongoing management so your home is optimized for revenue on Airbnb and other platforms. Start with Awning’s get started page.

How does Awning compare to Vacasa?

Awning delivers full-service management at a lower starting percentage and greater fee transparency than Vacasa, which typically charges higher rates with additional service costs. See Vaasa Fees explained.

How does Awning compare to Evolve?

Unlike Evolve’s half-service model, Awning provides full operational support including cleaning, pricing, and guest communication for a truly hands-off experience. More on full vs half service.

Does Awning offer insurance for hosts and their properties?

Awning provides tailored insurance options that cover property and income risks related to short-term rental activity. Ask your advisor for a tailored quote.

Will Awning maintain amenities like pools and hot tubs?

Yes — Awning coordinates maintenance for features like pools, hot tubs, and outdoor areas so amenities remain guest-ready and compliant. These are part of Awning’s property maintenance services.

What is the pet policy for properties under Awning management?

Pet policies are set by the property owner. Awning supports owner-defined pet rules and can assist with additional cleaning or maintenance plans as needed. Link to your preferences via Awning support.

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