Florida Keys holiday rentals

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
Private kitchen
Dining
Exceptional
(5 reviews)

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

Key Largo

7% off
AU$3,435
for 7 nights, 1 cottage
AU$491 per night
includes taxes & fees
Charming and Cozy ,2/2 in Key Largo,Where Island Vibes and Adventures Await You.
View from the lanai. 🐠🌴☀️🎣
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
AU$6,834
for 7 nights, 1 home
AU$976 per night
includes taxes & fees
Beautiful Canal front w/ dock - private pool -4/3~walk to beach~Outdoor smart tv
Pool
Exterior detail
Interior
Dining
Very good
(6 reviews)

New Keys Cabins. Family sized cabins with full kitchens,

Marathon

8% off
AU$3,437
for 7 nights, 1 cabin
AU$491 per night
includes taxes & fees
New Keys Cabins. Family sized cabins with full kitchens,
Interior
Pool
Its not a Mirage...its Mirage Manor
If Bananas are ripe then eat em
Exceptional
(38 reviews)

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

Marathon

8% off
AU$6,371
for 7 nights, 1 home
AU$910 per night
includes taxes & fees
Marathon 3BR on 55' Canal Boat Dock w Pool Spa Hot Tub Free pool heat bay side
Interior
Property grounds
Dining
Room
Exceptional
(54 reviews)

Convenient central Marathon location, canal view.

Marathon

7% off
AU$2,091
for 7 nights, 1 home
AU$299 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
AU$4,850
for 7 nights, 1 apartment
AU$693 per night
includes taxes & fees
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
Living room
Marina
Kitchen
Outdoor dining
Exceptional
(11 reviews)

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

Key Largo

7% off
AU$1,701
for 7 nights, 1 home
AU$243 per night
includes taxes & fees
The Newly Renovated Couples Retreat in Key Largo , Pool beach , and Marina
Marina
Pool
Property grounds
Exterior
Exceptional
(18 reviews)

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

Key West

8% off
AU$8,324
for 7 nights, 1 home
AU$1,189 per night
includes taxes & fees
Funky Chicken Cottage with shared pool, 3 bed 3 bath minutes from Key West
Conch Cottage from above, with so much more outdoor space than our neighbors.
A common walkway leads to Conch Cottage: Vacation vibes on Harbor Village Drive!
Canal-side living! Say hello to passing boaters, paddlers & kayakers.
Enjoy a morning coffee out on your private balcony.
Wonderful
(9 reviews)

Hawks Cay Island Retreat - Duck Key - Pool & Patio

Marathon

8% off
AU$4,739
for 7 nights, 1 villa
AU$677 per night
includes taxes & fees
Hawks Cay Island Retreat - Duck Key - Pool & Patio
Back of clubhouse next to pool
Back porch with pool view
Living area
Side view of condo
Exceptional
(208 reviews)

Casa Caribe Beautiful tropical 2 bedroom sleeps 6

Key West

8% off
AU$6,826
for 7 nights, 1 home
AU$975 per night
includes taxes & fees
Casa Caribe Beautiful tropical 2 bedroom sleeps 6
Living area
Marina
Interior
Pool
Exceptional
(52 reviews)

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

Key Largo

8% off
AU$2,974
for 7 nights, 1 home
AU$425 per night
includes taxes & fees
Tiny house in the Florida Keys with Deck and Marina with boat ramp
Pool
Interior
Living area
Marina
Exceptional
(89 reviews)

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

Tavernier

7% off
AU$2,874
for 7 nights, 1 apartment
AU$411 per night
includes taxes & fees
Breathtaking Ocean views! Owners who care. “Sangria Sunrise”! 10% off charters!
Downstairs area
Second pool
Sports court
Oceanfront  Seating
Exceptional
(17 reviews)

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

Key Largo

8% off
AU$4,568
for 7 nights, 1 home
AU$653 per night
includes taxes & fees
NEW LISTING! Key Largo Oceanside Townhouse with Private Marina, Lagoon, & Pools
The Maison Property, beach, pool, summer kitchen and day dock from the Atlantic.
Sunrise over the large Maison resort style pool.
Gated entrance to the Maison Property.
Great room with sliding glass doors to balcony deck.
Exceptional
(76 reviews)

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

Islamorada

8% off
AU$7,605
for 7 nights, 1 apartment
AU$1,086 per night
includes taxes & fees
Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
Living area
Property grounds
Private kitchen
Room
Exceptional
(5 reviews)

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

Summerland Key

6% off
AU$5,057
for 7 nights, 1 home
AU$722 per night
includes taxes & fees
Warm and relax 3-bed 2 bath home in charming Summerland Key minutes from K.West
Bedroom one has a memory foam mattress, 100% cotton sheets,  and 50" Roku TV.
Sun bathe and relax in the sun with these comfy chaise loungers!
Plenty of comfy seating to plan out your Key Largo adventure!
Cook a wonderful dinner in this fully stocked kitchen!
Exceptional
(26 reviews)

Jaw-dropping Canal View Key Largo Boat Slip, Bay

Key Largo

8% off
AU$4,791
for 7 nights, 1 apartment
AU$684 per night
includes taxes & fees
Jaw-dropping Canal View Key Largo Boat Slip, Bay
Dining
Room
Interior
Private kitchen
Wonderful
(21 reviews)

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

Marathon

7% off
AU$2,795
for 7 nights, 1 home
AU$399 per night
includes taxes & fees
Charming 2beds 2 baths w/pool 10 mins from the beach!
PICNIC AREA
Largest lagoon pool night view
Main Dining Room
Access to Private Roof Top
Exceptional
(22 reviews)

True Key Largo Luxury!

Key Largo

8% off
AU$6,071
for 7 nights, 1 home
AU$867 per night
includes taxes & fees
True Key Largo Luxury!
Property grounds
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
AU$3,708
for 7 nights, 1 home
AU$530 per night
includes taxes & fees
Key Colony Beach Home Casa Sunny Sea Key Colony Beach, Fl Keys
Pull out sofa bed w/ comfortable  mattress. Property #2178313 for more reviews
Pool
Flat screen Smart TV in living room with HBO & Showtime anytime
Dock you boat here. Underwater lighting for night fishing off of the dock. Fun!
Exceptional
(39 reviews)

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

Key Colony Beach

7% off
AU$3,748
for 7 nights, 1 home
AU$535 per night
includes taxes & fees
Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!
Bright and blue, pool is heated December to March! Private pool and tiki bar..
Bay views from the bar 🌘, Book your Holiday & 2024 dates now!
Privacy bamboo fence
Cozy & comfy, perfect for family & friends time🌴
Exceptional
(135 reviews)

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

Key Colony Beach

8% off
AU$4,346
for 7 nights, 1 home
AU$621 per night
includes taxes & fees
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
Property grounds
Pool
The best deep water marina in Key West, with dry slips & wet slips available.
Living area
Exceptional
(154 reviews)

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

Key West

8% off
AU$5,093
for 7 nights, 1 apartment
AU$728 per night
includes taxes & fees
'Oceanside Oasis' Direct Ocean Views & 3 BR'S
Marina and our building at night
Marina walkway at night
Club house at Night
Pool Area and Bar at Oceanpointe
Exceptional
(149 reviews)

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

Tavernier

7% off
AU$3,847
for 7 nights, 1 apartment
AU$550 per night
includes taxes & fees
OCEANVIEW / OCEANFRONT APARTMENT WITH RESORT AMENITIES, KEY LARGO, TAVERNIER
Living Room Seating Area with mirrored wall brings another view of ocean inside!
North Beach area with new firepits, bbq's, Adirondack chairs & Tiki huts
Tower has a beautiful open air atrium in the middle of it!
Heated salt-water Middle Pool is also available for your use
Exceptional
(317 reviews)

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

Key Largo

8% off
AU$2,685
for 7 nights, 1 apartment
AU$384 per night
includes taxes & fees
Last Minute Aug'26 Deals! OCEANFRNT Lux 1350sf, Great Views &All Amenities Home!
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    Enjoy full kitchens, laundry, pools, gardens and more
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    More space, more privacy, more amenities — more value

Why visit Florida Keys

  • Stunning beaches: The Florida Keys boast beautiful sandy shores, perfect for relaxation and sunbathing.
  • Outdoor adventures: Engage in thrilling activities like snorkelling, diving, and kayaking in vibrant marine environments.
  • Cultural experiences: Discover local history and art in charming towns, including vibrant festivals and lively squares.
  • National parks: Explore breathtaking landscapes and diverse wildlife in protected areas, ideal for nature enthusiasts.
  • Unique accommodations: Enjoy a range of lodging options, from cosy cottages to modern condos, catering to all budgets.

Popular types of accommodation around Florida Keys

Discover the charm of Florida Keys, United States of America, where you can find private holiday homes, cosy cottages, and modern condos. Whether you're seeking budget accommodations or luxury experiences, there's something for everyone. Enjoy free parking and even unique options like an aqua lodge. Explore local attractions, stunning beaches, and vibrant marine life, making your stay truly unforgettable.

  • Private Holiday Homes: The top choice for holiday stays in the Florida Keys, offering spacious and comfortable living for families and groups.
  • Condos: A popular option that combines convenience and amenities, ideal for those seeking a home-away-from-home experience.
  • Cottages: These charming retreats provide a quaint atmosphere, perfect for a relaxing getaway by the water.
  • Apartments: A flexible choice for couples or solo travellers, offering essential facilities in a compact setting.
  • Villas: Luxurious accommodations that provide privacy and upscale features, perfect for indulgent stays.**

Top attractions near Florida Keys

The Florida Keys offer a delightful holiday experience with stunning beaches, outdoor adventures, and family-friendly activities. Visitors can explore captivating national parks, historic civic buildings, and vibrant squares, all while soaking up the local culture. Whether you're seeking relaxation or adventure, the Keys provide a perfect backdrop for unforgettable experiences beneath the sun, making it an ideal destination for travellers of all kinds.

  • Mallory Square: A vibrant hub in Key West, Mallory Square is renowned for its lively atmosphere, featuring street performers, local artisans, and stunning sunset views over the Gulf of Mexico, making it a perfect spot for evening relaxation.
  • Fort Zachary Taylor Historic State Park: This historical site offers a blend of adventure and natural beauty, with opportunities for exploring the well-preserved fort, enjoying picturesque beach scenery, and indulging in outdoor activities like swimming and picnicking.
  • Florida Keys National Marine Sanctuary: A haven for marine enthusiasts, this sanctuary provides thrilling experiences such as snorkelling and diving amidst vibrant coral reefs, making it an ideal destination for family adventures and marine exploration.

Things to do recommended for couples

Seeking a romantic getaway in the Florida Keys? Enjoy a candlelit dinner at a seaside restaurant or take a sunset sail, soaking in the stunning views. Don't miss a leisurely bike ride along the scenic coastline, perfect for couples to connect amidst the beautiful surroundings.

Things to do recommended for families

Families can explore the delightful John Pennekamp Coral Reef State Park, where snorkelling and glass-bottom boat tours reveal vibrant marine life. For a unique experience, visit the Dolphin Research Centre, where kids can interact with friendly dolphins while learning about marine conservation.

Things to do recommended for groups

Explore the vibrant marine life with a group snorkelling trip at John Pennekamp Coral Reef State Park or indulge in a sunset dinner cruise, enjoying the stunning views of the Florida Keys' coastline while savouring local seafood delicacies.

*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 journeying with a group, as a family, with your pets, or planning a longer stay, be sure to apply the appropriate filters. Here are some Stayz booking recommendations 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 all of these options and more on Stayz.
  • Traveling to Florida Keys with young kids: Traveling with young children can be demanding. You must prioritise their comfort and safety, along with access to age-appropriate facilities such as a private swimming pool. It’s also wise to consider your closeness to attractions suitable for families.
  • Taking your pets with you to Florida Keys: For some, a family holiday isn’t complete without their four-legged companion by their side. If this resonates with you, then explore Stayz properties that welcome pets. Many pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels right at home.
  • Planning for a long term stay visiting Florida Keys: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Florida Keys

Discover the charm of the Florida Keys, an enchanting island paradise perfect for beach escapes and family adventures. Explore the vibrant Key West, immerse in tropical excursions, and enjoy serene moments on the best islands. From historical sites to romantic coastal retreats, every corner of the Keys offers a unique blend of outdoor and cultural experiences, making it an idyllic destination for a memorable holiday.

  • Key West: Key West is a charming island city located 10km from the heart of the Florida Keys. With its natural island charm, visitors can enjoy a blend of family attractions, urban sophistication and business amenities. The area offers a variety of activities, including exploring the local shopping district and a modern shopping centre. Notable landmarks nearby include sandy beaches and vibrant streets that capture the lively spirit of the city.
  • Old Town Key West: Old Town Key West is a historic neighbourhood situated 11km from the Florida Keys. This area offers a rich mix of city culture, family-friendly attractions and business opportunities. Wander through its quaint streets, explore local shopping areas and enjoy the ambience of a traditional shopping centre. The neighbourhood is renowned for its charming street views, sandy beaches and cosy family-friendly beach spots.
  • Sunset Key: Sunset Key is a delightful neighbourhood located 10km from the Florida Keys. It presents visitors with a fusion of urban appeal, family attractions and business-oriented experiences. Stroll through the local shopping centre and explore nearby shopping areas. The key attractions include beautiful beaches, inviting family beach settings and scenic streets, providing a comprehensive experience for every traveller.

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. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

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

Booking with Stayz is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay often results in significant savings. To discover the ideal Stayz property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board provides a dedicated area for you to plan new trips, manage your existing arrangements, or review your bookings. The properties you’ve saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover your Trip Boards, please visit: https://www.stayz.com.au/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? Stayz 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 Stayz. 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 Stayz 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 Stayz.
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 Stayz.
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 Stayz, 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.