Florida Keys holiday homes

We found 7,672 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Florida Keys

Showing deals for:20 Nov - 27 Nov

Interior
Living area
Dining
Private kitchen
Exceptional
(5 reviews)

Charming and Cozy ,2/2 in Key Largo,Where Island Vibes and Adventures Await You.

Key Largo

7% off
NZ$4,143
for 7 nights, 1 cottage
NZ$592 per night
includes taxes & fees
Charming and Cozy ,2/2 in Key Largo,Where Island Vibes and Adventures Await You.
Roomy kitchen
Exterior
Upstairs Lanai
Pool
Exceptional
(111 reviews)

Beautiful Canal front w/ dock - private pool -4/3~walk to beach~Outdoor smart tv

Marathon

8% off
NZ$8,295
for 7 nights, 1 home
NZ$1,185 per night
includes taxes & fees
Beautiful Canal front w/ dock - private pool -4/3~walk to beach~Outdoor smart tv
Room
Exterior detail
Pool
Dining
Very good
(6 reviews)

New Keys Cabins. Family sized cabins with full kitchens,

Marathon

8% off
NZ$4,145
for 7 nights, 1 cabin
NZ$592 per night
includes taxes & fees
New Keys Cabins. Family sized cabins with full kitchens,
If Bananas are ripe then eat em
Pool
Its not a Mirage...its Mirage Manor
Interior
Exceptional
(38 reviews)

Marathon 3BR on 55' Canal Boat Dock w Pool Spa Hot Tub Free pool heat bay side

Marathon

8% off
NZ$7,740
for 7 nights, 1 home
NZ$1,106 per night
includes taxes & fees
Marathon 3BR on 55' Canal Boat Dock w Pool Spa Hot Tub Free pool heat bay side
Room
Property grounds
Marina
Dining
Exceptional
(54 reviews)

Convenient central Marathon location, canal view.

Marathon

7% off
NZ$2,472
for 7 nights, 1 home
NZ$353 per night
includes taxes & fees
Convenient central Marathon location, canal view.
LA BRISA BEACHFRONT GATED CONDO COMMUNITY
Outdoor dining
Living area
Boondock's Mini Golf
Wonderful
(152 reviews)

GATED OCEANFRONT CONDO AT SMATHER'S BEACH

Key West

8% off
NZ$5,918
for 7 nights, 1 apartment
NZ$845 per night
includes taxes & fees
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
Kitchen
Marina
Outdoor dining
Dining
Exceptional
(11 reviews)

The Newly Renovated Couples Retreat in Key Largo , Pool beach , and Marina

Key Largo

7% off
NZ$2,055
for 7 nights, 1 home
NZ$294 per night
includes taxes & fees
The Newly Renovated Couples Retreat in Key Largo , Pool beach , and Marina
Interior
Pool
Marina
Property grounds
Exceptional
(18 reviews)

Funky Chicken Cottage with shared pool, 3 bed 3 bath minutes from Key West

Key West

8% off
NZ$10,158
for 7 nights, 1 home
NZ$1,451 per night
includes taxes & fees
Funky Chicken Cottage with shared pool, 3 bed 3 bath minutes from Key West
Enjoy a morning coffee out on your private balcony.
A common walkway leads to Conch Cottage: Vacation vibes on Harbor Village Drive!
Kick back, read, play board games & watch TV in the well-appointed living area.
Canal-side living! Say hello to passing boaters, paddlers & kayakers.
Wonderful
(9 reviews)

Hawks Cay Island Retreat - Duck Key - Pool & Patio

Marathon

8% off
NZ$5,817
for 7 nights, 1 villa
NZ$831 per night
includes taxes & fees
Hawks Cay Island Retreat - Duck Key - Pool & Patio
Living area
Back porch with pool view
Beautiful large heated pool
Back of clubhouse next to pool
Exceptional
(208 reviews)

Casa Caribe Beautiful tropical 2 bedroom sleeps 6

Key West

8% off
NZ$8,283
for 7 nights, 1 home
NZ$1,183 per night
includes taxes & fees
Casa Caribe Beautiful tropical 2 bedroom sleeps 6
Living area
Marina
Pool
Private kitchen
Exceptional
(52 reviews)

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

Key Largo

8% off
NZ$3,561
for 7 nights, 1 home
NZ$509 per night
includes taxes & fees
Tiny house in the Florida Keys with Deck and Marina with boat ramp
Living area
Interior
Pool
Marina
Exceptional
(89 reviews)

Breathtaking Ocean views! Owners who care. “Sangria Sunrise”! 10% off charters!

Tavernier

7% off
NZ$3,442
for 7 nights, 1 apartment
NZ$492 per night
includes taxes & fees
Breathtaking Ocean views! Owners who care. “Sangria Sunrise”! 10% off charters!
Sports court
Second pool
Oceanfront  Seating
Kitchen
Exceptional
(17 reviews)

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

Key Largo

8% off
NZ$5,609
for 7 nights, 1 home
NZ$801 per night
includes taxes & fees
NEW LISTING! Key Largo Oceanside Townhouse with Private Marina, Lagoon, & Pools
Propane fire pit and Adirondack chairs.
Sunrise over the large Maison resort style pool.
Gated entrance to the Maison Property.
The Maison Property, beach, pool, summer kitchen and day dock from the Atlantic.
Exceptional
(76 reviews)

Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock

Islamorada

8% off
NZ$9,288
for 7 nights, 1 apartment
NZ$1,327 per night
includes taxes & fees
Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
Property grounds
Property grounds
Room
Private kitchen
Exceptional
(5 reviews)

Warm and relax 3-bed 2 bath home in charming Summerland Key minutes from K.West

Summerland Key

6% off
NZ$6,171
for 7 nights, 1 home
NZ$882 per night
includes taxes & fees
Warm and relax 3-bed 2 bath home in charming Summerland Key minutes from K.West
Cook a wonderful dinner in this fully stocked kitchen!
Sun bathe and relax in the sun with these comfy chaise loungers!
Bedroom one has a memory foam mattress, 100% cotton sheets,  and 50" Roku TV.
Plenty of comfy seating to plan out your Key Largo adventure!
Exceptional
(26 reviews)

Jaw-dropping Canal View Key Largo Boat Slip, Bay

Key Largo

8% off
NZ$5,847
for 7 nights, 1 apartment
NZ$835 per night
includes taxes & fees
Jaw-dropping Canal View Key Largo Boat Slip, Bay
Interior
Room
Private kitchen
Dining
Wonderful
(21 reviews)

Charming 2beds 2 baths w/pool 10 mins from the beach!

Marathon

7% off
NZ$3,347
for 7 nights, 1 home
NZ$478 per night
includes taxes & fees
Charming 2beds 2 baths w/pool 10 mins from the beach!
Master Suite with king bed and sitting area
Largest lagoon pool night view
Access to Private Roof Top
Main Dining Room
Exceptional
(22 reviews)

True Key Largo Luxury!

Key Largo

8% off
NZ$7,383
for 7 nights, 1 home
NZ$1,055 per night
includes taxes & fees
True Key Largo Luxury!
Exterior
Pool
Property grounds
Private kitchen
Exceptional
(11 reviews)

Key Colony Beach Home Casa Sunny Sea Key Colony Beach, Fl Keys

Key Colony Beach

7% off
NZ$4,554
for 7 nights, 1 home
NZ$651 per night
includes taxes & fees
Key Colony Beach Home Casa Sunny Sea Key Colony Beach, Fl Keys
Dock you boat here. Underwater lighting for night fishing off of the dock. Fun!
Pool
Flat screen Smart TV in living room with HBO & Showtime anytime
Pull out sofa bed w/ comfortable  mattress. Property #2178313 for more reviews
Exceptional
(39 reviews)

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

Key Colony Beach

7% off
NZ$4,602
for 7 nights, 1 home
NZ$657 per night
includes taxes & fees
Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!
Cozy & comfy, perfect for family & friends time🌴
Bay views from the bar 🌘, Book your Holiday & 2024 dates now!
Privacy bamboo fence
Bright and blue, pool is heated December to March! Private pool and tiki bar..
Exceptional
(135 reviews)

CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!

Key Colony Beach

8% off
NZ$5,336
for 7 nights, 1 home
NZ$762 per night
includes taxes & fees
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
Property grounds
Pool
Living area
Living area
Exceptional
(154 reviews)

'Oceanside Oasis' Direct Ocean Views & 3 BR'S

Key West

8% off
NZ$6,215
for 7 nights, 1 apartment
NZ$888 per night
includes taxes & fees
'Oceanside Oasis' Direct Ocean Views & 3 BR'S
Marina and our building at night
Marina walkway at night
Pool Area and Bar at Oceanpointe
Club house at Night
Exceptional
(149 reviews)

OCEANVIEW / OCEANFRONT APARTMENT WITH RESORT AMENITIES, KEY LARGO, TAVERNIER

Tavernier

7% off
NZ$4,724
for 7 nights, 1 apartment
NZ$675 per night
includes taxes & fees
OCEANVIEW / OCEANFRONT APARTMENT WITH RESORT AMENITIES, KEY LARGO, TAVERNIER
Heated salt-water Middle Pool is also available for your use
North Beach area with new firepits, bbq's, Adirondack chairs & Tiki huts
Living Room Seating Area with mirrored wall brings another view of ocean inside!
View overlooking Yacht Club Marina and Atlantic Ocean from our Balcony
Exceptional
(317 reviews)

Last Minute Aug'26 Deals! OCEANFRNT Lux 1350sf, Great Views &All Amenities Home!

Key Largo

8% off
NZ$3,216
for 7 nights, 1 apartment
NZ$459 per night
includes taxes & fees
Last Minute Aug'26 Deals! OCEANFRNT Lux 1350sf, Great Views &All Amenities Home!
  • 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.