Florida Keys holiday homes

We found 7,666 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Florida Keys

Showing deals for:1 Jan - 8 Jan

Interior
Marina
Marina
Marina
Exceptional
(62 reviews)

Living the Dream Key West Style

Key West

8% off
NZ$4,393
for 7 nights, 1 houseboat
NZ$628 per night
includes taxes & fees
Living the Dream Key West Style
Private kitchen
Marina
Pool
Living area
Exceptional
(53 reviews)

Tiny house in the Florida Keys with Deck and Marina with boat ramp

Key Largo

8% off
NZ$3,763
for 7 nights, 1 home
NZ$538 per night
includes taxes & fees
Tiny house in the Florida Keys with Deck and Marina with boat ramp
Living area
Pool
Interior
Terrace/patio
Exceptional
(31 reviews)

Sun Bake @ Sponge Cake, 64' Sea Wall,

Summerland Key

8% off
NZ$5,225
for 7 nights, 1 home
NZ$746 per night
includes taxes & fees
Sun Bake @ Sponge Cake, 64' Sea Wall,
Plenty of comfy seating to plan out your Key Largo adventure!
Sun bathe and relax in the sun with these comfy chaise loungers!
Cook a wonderful dinner in this fully stocked kitchen!
Bedroom one has a memory foam mattress, 100% cotton sheets,  and 50" Roku TV.
Exceptional
(27 reviews)

Jaw-dropping Canal View Key Largo Boat Slip, Bay

Key Largo

8% off
NZ$8,196
for 7 nights, 1 apartment
NZ$1,171 per night
includes taxes & fees
Jaw-dropping Canal View Key Largo Boat Slip, Bay
Marina
Property grounds
Room
Interior
Exceptional
(12 reviews)

Oasis by the Sea. Key Largo Getaway.

Key Largo

8% off
NZ$3,326
for 7 nights, 1 home
NZ$475 per night
includes taxes & fees
Oasis by the Sea. Key Largo Getaway.
Marina
Interior
Living area
View from our condo
Exceptional
(62 reviews)

Rare Key Largo Moon Bay condo with 3 bdrm & 2.5 baths!! Min 6 night stay please!

Key Largo

8% off
NZ$6,759
for 7 nights, 1 apartment
NZ$966 per night
includes taxes & fees
Rare Key Largo Moon Bay condo with 3 bdrm & 2.5 baths!! Min 6 night stay please!
Walking distance to Duck Key Marina, water sports and a small beach.
Situated in a Gated Community
Private heated pool with plenty of seating and outdoor games
Outdoor Dining
Exceptional
(42 reviews)

Private Pool Oasis - Centrally Located in Florida Keys

Marathon

8% off
NZ$9,846
for 7 nights, 1 home
NZ$1,407 per night
includes taxes & fees
Private Pool Oasis - Centrally Located in Florida Keys
Kitchen
Second pool
Downstairs area
Sports court
Exceptional
(17 reviews)

NEW LISTING! Key Largo Oceanside Townhouse with Private Marina, Lagoon, & Pools

Key Largo

8% off
NZ$5,143
for 7 nights, 1 home
NZ$735 per night
includes taxes & fees
NEW LISTING! Key Largo Oceanside Townhouse with Private Marina, Lagoon, & Pools
Pool
Exterior detail
Room
Dining
Very good
(6 reviews)

New Keys Cabins. Family sized cabins with full kitchens,

Marathon

8% off
NZ$4,378
for 7 nights, 1 cabin
NZ$625 per night
includes taxes & fees
New Keys Cabins. Family sized cabins with full kitchens,
Flat screen Smart TV in living room with HBO & Showtime anytime
Pool
Pull out sofa bed w/ comfortable  mattress. Property #2178313 for more reviews
Over the rainbow
Exceptional
(42 reviews)

Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!

Key Colony Beach

8% off
NZ$5,789
for 7 nights, 1 home
NZ$827 per night
includes taxes & fees
Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!
Private kitchen
Terrace/patio
Pool
Room
Exceptional
(24 reviews)

Resort-style condo short walk from the ocean, includes golf cart.

Key Largo

8% off
NZ$6,800
for 7 nights, 1 apartment
NZ$971 per night
includes taxes & fees
Resort-style condo short walk from the ocean, includes golf cart.
Dining
Beach
Interior
Private kitchen
Exceptional
(10 reviews)

Escape Winter in the Florida Keys ☀️ Marathon Snowbird Retreat Few Dates Left!

Marathon

7% off
NZ$3,108
for 7 nights, 1 villa
NZ$444 per night
includes taxes & fees
Escape Winter in the Florida Keys ☀️ Marathon Snowbird Retreat Few Dates Left!
Heated pool at Coral Hammock huge pool gated
Pool view from upstairs porch lush landscaping around house
Custom closet downstairs
Pool view from upstairs back porch
Exceptional
(413 reviews)

Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach

Key West

8% off
NZ$11,695
for 7 nights, 1 home
NZ$1,671 per night
includes taxes & fees
Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
Exterior
Exterior
Marina
Private kitchen
Exceptional
(204 reviews)

Finest location in Coral Lagoon. End unit with open water bay and marina views.

Marathon

8% off
NZ$9,647
for 7 nights, 1 home
NZ$1,378 per night
includes taxes & fees
Finest location in Coral Lagoon. End unit with open water bay and marina views.
Pool
Marina
Property grounds
Private kitchen
Exceptional
(11 reviews)

R & R in Paradise

Key Largo

7% off
NZ$3,460
for 7 nights, 1 home
NZ$494 per night
includes taxes & fees
R & R in Paradise
Get lost enjoying the canal view and watch nature go by from the balcony!
Relax, unwind, and put your feet up in these cozy chaise loungers!
Plenty of comfy seating to plan out your Key Largo adventure!
Room
Exceptional
(58 reviews)

Boater’s Family Retreat in Key Largo with Waterfront Views and Dock Access

Key Largo

8% off
NZ$8,227
for 7 nights, 1 apartment
NZ$1,175 per night
includes taxes & fees
Boater’s Family Retreat in Key Largo with Waterfront Views and Dock Access
Private kitchen
Terrace/patio
Marina
Room
Exceptional
(40 reviews)

Waterfront Key Largo Escape with Boat Slip and Beautiful Sunrise Views

Key Largo

8% off
NZ$8,900
for 7 nights, 1 apartment
NZ$1,271 per night
includes taxes & fees
Waterfront Key Largo Escape with Boat Slip and Beautiful Sunrise Views
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Florida Keys

  • Island Beauty: Revel in the tropical allure of crystal-clear waters and pristine beaches, perfect for swimming and water sports.
  • Outdoor Adventures: Enjoy island-hopping, kayaking, and exploring national parks that showcase the Keys' natural splendour.
  • Historic Charm: Discover local heritage through historic civic buildings and sites that tell the tale of the Keys' past.
  • Cultural Vibes: Experience vibrant local life in modern squares and community hubs, rich in local traditions.
  • Sunset Magic: Witness breathtaking sunsets that paint the sky with romantic hues over the Atlantic and Gulf.

Top attractions near Florida Keys

Florida Keys offers a blend of beach, outdoor, and family experiences perfect for any traveller. Discover modern squares, national and state parks, and historic civic buildings that showcase the region's rich culture and adventurous spirit. Whether you’re exploring nature or delving into local history, there’s plenty in Florida Keys to make your holiday memorable.

  • Fort Zachary Taylor Historic State Park: Experience scenic outdoor adventures at this national state park located 10km from the Florida Keys, where history meets nature.
  • Truman Beach: Enjoy the relaxed beach vibes at this inviting seaside destination, also 10km from the Florida Keys.
  • Curry Mansion Museum: Delve into local culture and history at this museum, situated 10km from the Florida Keys, offering a glimpse into the region’s past.

Things to do recommended for couples

Ready for a romantic getaway in the Florida Keys? Explore the stunning sunsets at Mallory Square, indulge in a sunset sail, or cuddle up on the beach at Key Largo. A visit to a charming café or a scenic bike ride along the Overseas Highway adds to the magic.

Things to do recommended for families

Families visiting the Florida Keys can enjoy a fun day exploring the Turtle Hospital, a hands-on wildlife experience, and kayaking through mangroves, offering a true taste of local life.

Things to do recommended for groups

Groups exploring the Florida Keys can enjoy a vibrant local experience with water sports, island hopping, and delicious seafood feasts, capturing the unique island vibe and laid-back culture perfect for Kiwis seeking adventure and relaxation.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Florida Keys

Whether you're travelling with a group, as a family, with your pets, or seeking extended stays, be sure to apply the appropriate filters. Here are some Vrbo booking tips for you.

  • Traveling to Florida Keys with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Florida Keys with young kids: Traveling with little ones can be a challenge. You must ensure their comfort and safety, along with age-appropriate amenities like a private pool. It’s also wise to consider how close you are to family-friendly attractions.
  • Taking your pets with you to Florida Keys: Some travellers wouldn’t consider a family holiday complete without their furry companion. If that describes you, take a look at Vrbo properties that welcome pets. Many of these homes also offer feeding bowls and beds, ensuring a comfortable stay for every member of the family.
  • Planning for a long term stay visiting Florida Keys: If you’re after holiday rentals offering discounts for month-long stays, you’ve come to the right spot. With the appropriate filter, you can effortlessly locate and save on monthly rentals. Be sure to include options like a parking space, a quality kitchen, or a private pool in your search as well.

Where to stay near Florida Keys

Discover the enchanting islands of the Florida Keys, perfect for beach lovers and families. Enjoy tropical vibes, captivating history, and romantic sunsets on Key Largo and beyond. With scenic sightseeing spots and cozy holiday options, the Keys offer an ideal escape for any traveller seeking a blend of outdoor adventure and laid-back island charm.

  • Key West: Key West is an enchanting island city located 10km from the Florida Keys. Known for its vibrant atmosphere, this destination offers a delightful combination of family-friendly activities, business opportunities, and a rich cultural tapestry. Visitors can explore a variety of shopping areas and enjoy its renowned beaches, perfect for a day of sun and sand. Key West is also famous for its lively streets filled with eclectic shops and dining options, making it an ideal spot for both relaxation and adventure.
  • Old Town Key West: Situated 11km from the Florida Keys, Old Town Key West is a charming neighbourhood brimming with character and history. This area is perfect for those seeking a city-themed experience, with family-friendly attractions and business amenities at hand. Stroll along picturesque streets, indulge in shopping, and unwind at nearby beaches, including family-friendly options that cater to all ages. The vibrant atmosphere and unique architecture create a welcoming environment for visitors looking to immerse themselves in local culture.
  • Sunset Key: Just 10km from the Florida Keys, Sunset Key is a picturesque neighbourhood known for its stunning sunsets and laid-back vibe. Travelers flock here for its city-themed charm, family-friendly spots, and business facilities. Enjoy leisurely days exploring shopping areas and resorts while taking in the breathtaking views from the beach. With its tranquil streets and inviting atmosphere, Sunset Key is an ideal destination for those looking to relax and soak up the natural beauty of the surroundings.

Best time to go to Florida Keys

If you're planning a trip to Florida Keys, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January70.9°F (21.6°C)No Rain (Dry)Mostly Sunny
February72.1°F (22.3°C)No Rain (Dry)Mostly Sunny
March73.2°F (22.9°C)No Rain (Dry)Mostly Sunny
April76.8°F (24.9°C)No Rain (Dry)Mostly Sunny
May79.3°F (26.3°C)Light RainMostly Sunny
June82.6°F (28.1°C)Light RainMostly Sunny
July84.0°F (28.9°C)Light RainMostly Sunny
August84.4°F (29.1°C)Light RainMostly Sunny
September83.5°F (28.6°C)Light RainMostly Sunny
October80.6°F (27.0°C)Light RainMostly Sunny
November76.5°F (24.7°C)Light RainMostly Sunny
December73.6°F (23.1°C)No Rain (Dry)Mostly Sunny

Booking with Vrbo is a breeze

Are you keen to save on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides you with a dedicated area to start new adventures, continue planning, or neatly organise your bookings. Your saved or reserved properties are now categorised into Potential, Upcoming, or Current Trips. To explore Trip Boards, visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Lively Florida Keys will entice you

Enjoy the live music and other features of Florida Keys. Renowned for its dolphin watching, seaside and bars, this city welcomes all visitors. Florida Keys Beaches and Duval Street are just a couple of the must-see attractions. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Florida Keys

Are you looking for attractions to visit during your stay? Travellers enjoy fun activities like jogging trails, dolphin viewing and fishing. Venture out of your holiday home and check out everything that makes Florida Keys a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Florida Keys Country Club (8.1 mi / 13 km)
  • Blue Hole (14.9 mi / 24 km)

Exploring the beaches and other natural features in Florida Keys

Travellers appreciate the breathtaking sunsets and beautiful ocean views, which is just a taste of what Florida Keys has to offer. Whether you're an active traveller or just want to take in the scenery, Florida Keys is a great place to get out in nature. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Florida Keys Beaches (27.7 mi / 44.6 km)
  • Pigeon Key (6.6 mi / 10.6 km)
  • Vaca Key (7 mi / 11.2 km)
  • Sombrero Beach (8.9 mi / 14.3 km)
  • Sunset Park Beach (10.4 mi / 16.7 km)
  • Coco Plum Beach (11.3 mi / 18.2 km)

How to get to and around Florida Keys

The nearest airport is in Marathon, FL (MTH-Florida Keys Marathon), located 8.7 mi (14.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Key West, FL (EYW-Key West Intl.), which is 40.8 mi (65.7 km) away.

Frequently asked questions

What is the best area to stay in Florida Keys when booking a holiday home?
Key West is one of the most preferred areas to select a holiday home in Florida Keys. Searching for some top things to do and see here? Be sure to check out Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens.
What is the most popular type of holiday home accommodation in Florida Keys?
The most desirable types of holiday homes in Florida Keys are houses. Want something different? Bookabach offers a variety of options to match our guests' unique needs, so you'll see properties in lots of shapes and sizes. The perfect home away from home is waiting for you — lock in yours today.
How much does it cost to rent a holiday home in Florida Keys?
The average price for a holiday home in Florida Keys is determined by several factors, like property type, length of stay and time of year. Whether you're dreaming about a villa with space for extended family or a quaint cottage for just you and your sweetheart, just add your travel dates to see some great-value stays.
How much does it cost to rent a beach house in Florida Keys?
When you travel and the size and style of the property will help determine the cost of your beachside escape. Enter your Florida Keys travel dates to view your options on Bookabach. Looking for basics like WiFi, or perks like a private pool? Use the filters to pick the amenities and features you want in your holiday home.
What are popular home amenities in Florida Keys?
When it comes to home amenities that people look for in Florida Keys, a microwave oven, off-street parking options and a fridge are the most popular. With Bookabach holiday homes, you'll enjoy choices to suit your taste and style, whether you're on a trip with your partner, your family or even pets.
Are there large group holiday homes in Florida Keys?
Florida Keys has 708 holiday homes that can cater to 10 or more people. These stays come with the space and privacy you need to share good times with your favourite people.
What are the top attractions for families in Florida Keys?
There are loads of cool things to see and do with the family in Florida Keys, including:
  • Mallory Square
  • Duval Street
  • Smathers Beach
Can I find two-bedroom holiday homes in Florida Keys?
Florida Keys has 2,243 two-bedroom properties to pick from. Discover a holiday home with all the privacy and space you need at a fantastic price on Bookabach.
Are there holiday homes with WiFi in Florida Keys?
You'll have a choice of 2,095 holiday homes with WiFi in Florida Keys. If you want to disconnect from daily life during your trip, but still want to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How old do you have to be to rent a holiday home in Florida Keys?
The minimum age is usually 16, 18 or 21. It can vary between properties on Bookabach, so look at the rules of your preferred Florida Keys holiday home before making a booking.
How long can I rent a holiday home in Florida Keys for?
How long you can rent a holiday home in Florida Keys varies according to the property. Just enter your selected dates to see a list of options offering extended stays. With tons of amenities such as laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to discover somewhere perfect to call your home away from home in Florida Keys.