Florida Keys Holidays

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Florida Keys Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was S$1,704, price is now S$1,370 per person
S$1,370
per person
10 Mar - 13 Mar
found 21 hours ago
Return flight included
Chicago (ORD) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Good... The carpet needs deep cleaned. Stayed here before and room was newer/cleaner.

Reviewed on 26 Jan, 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was S$2,984, price is now S$2,038 per person
S$2,038
per person
10 Mar - 13 Mar
found 21 hours ago
Return flight included
Chicago (ORD) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!

Reviewed on 28 Jan, 2026

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Price was S$2,306, price is now S$1,812 per person
S$1,812
per person
10 Mar - 13 Mar
found 21 hours ago
Return flight included
Chicago (ORD) to Key West (EYW)
9.4/10 Exceptional! (390 reviews)
The room was good but very small. It wasn’t a major thing because we were not in it most of the day. Everything was clean and cleaning services were provided daily. The breakfast wasn’t what I was expecting, but it was a true continental breakfast I guess. Front desk help was great. We didn’t use the pool because it was cold weather when we were there.

Reviewed on 26 Jan, 2026

Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
New Town
Price was S$1,714, price is now S$1,383 per person
S$1,383
per person
10 Mar - 13 Mar
found 21 hours ago
Return flight included
Chicago (ORD) to Key West (EYW)
8.8/10 Excellent! (1,749 reviews)
Pool was excellent! Also hotel moped rental, and transportation to downtown was great!

Reviewed on 28 Jan, 2026

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was S$1,716, price is now S$1,403 per person
S$1,403
per person
10 Mar - 13 Mar
found 21 hours ago
Return flight included
Chicago (ORD) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
Wonderful place to stay. Facilities were great. There were three bar/ restaurants to choose from with all very good food. You could walk off site to a few other local places with very good food also. The room was clean. Staff was helpful.

Reviewed on 27 Jan, 2026

Where to stay in Florida Keys

Find the best Florida Keys areas and neighborhoods for the activities you enjoy most. Learn more about Florida Keys
Key West Historic District

Old Town Key West

2 out of top 10 points of interest in this area
5/5(6 area reviews)

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Florida Keys Beaches.

Find hotels in Old Town Key West

Things to do near Florida Keys

The Florida Keys are perfect for a beachside family holiday, offering a variety of outdoor activities. Visitors can enjoy excellent diving, free kayaks, and live music while exploring vibrant shopping areas and resorts. Ideal picnic spots enhance the experience, making it a delightful destination for both relaxation and adventure.

Shopping

Seven miles from the Florida Keys, The Kite House offers a delightful selection of unique gifts and souvenirs. Meanwhile, We Cycle Key West, located six miles away, is perfect for cycling enthusiasts wanting to explore the scenic beauty of the area.

Recreation

Relax at the MLK Community Pool & Community Center, offering a family-friendly outdoor atmosphere. Play a round at the Key West Golf Club, where sports enthusiasts can enjoy the lush surroundings. Experience the charm of the Red Barn Theater, a hub for romance and cultural entertainment just moments away.

Adventure

In the Florida Keys, experience thrilling snorkelling in the vibrant coral reefs of Key Largo, or embark on a kayaking adventure through the mangroves of Big Pine Key. For a unique experience, try parasailing over the turquoise waters of Key West for breathtaking views of the coastline.

Nightlife

The nightlife in the Florida Keys is vibrant and diverse. Enjoy live music at the Green Parrot Bar in Key West or sip cocktails at the iconic Sloppy Joe's. For a more relaxed evening, visit the Sunset Pier to take in stunning views while enjoying a laid-back atmosphere.

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

Find the best attractions near Florida Keys

The Florida Keys offers a perfect blend of beach and outdoor activities, making it ideal for family vacations. Visitors can explore modern squares, national parks, and historic civic government buildings, catering to those seeking cultural experiences. Don't miss the best beaches and attractions in Key West, where you'll find a vibrant atmosphere perfect for family adventures.

  • Mallory Square: Experience the vibrant atmosphere of Mallory Square, known for its lively sunset celebrations featuring street performers, artisans, and food vendors. This bustling square is the perfect spot to soak in the local culture while enjoying breathtaking views of the Gulf of Mexico.
  • Harry S. Truman Little White House: Step back in time at the Harry S. Truman Little White House, a historic government building that served as a winter retreat for President Truman. Explore its fascinating exhibits that showcase the rich political history and culture of Key West.
  • Key West Shipwreck Museum: Dive into maritime history at the Key West Shipwreck Museum, where you can learn about the daring lives of shipwreck salvagers. Engaging exhibits and artefacts bring the stories of the sea to life, making for an enlightening experience.

Best time to go to Florida Keys

The best time to visit Florida Keys can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Florida Keys falls in August, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature around Florida Keys falls in January, visitor numbers are average and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January70.9°F (21.6°C)No RainMostly SunnyAverageAverage
February72.1°F (22.3°C)No RainMostly SunnyAverageSlightly High
March73.2°F (22.9°C)No RainMostly SunnySlightly HighSlightly High
April76.8°F (24.9°C)No RainMostly SunnySlightly LowSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageAverage
July84.0°F (28.9°C)Light RainMostly SunnySlightly HighAverage
August84.4°F (29.1°C)Light RainMostly SunnyAverageSlightly Low
September83.5°F (28.6°C)Light RainMostly SunnySlightly LowSlightly Low
October80.6°F (27.0°C)Light RainMostly SunnySlightly LowSlightly Low
November76.5°F (24.700000000000003°C)Light RainMostly SunnyAverageAverage
December73.6°F (23.1°C)No RainMostly SunnySlightly HighAverage

Tips to save on your trip to Florida Keys

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Florida Keys.
  • Consider traveling to Florida Keys during the low season (August to October) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Top hotels in Florida Keys

Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is S$382 per night from 2 Feb to 3 Feb
S$382
2 Feb - 3 Feb
includes taxes & fees
9.2/10 Wonderful! (1,658 reviews)
Beautiful beach area. Friendly staff.

Reviewed on 25 Jan, 2026

Chesapeake Beach Resort
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
61 Hawks Cay Blvd Marathon FL
Fully refundableReserve now, pay when you stay
The price is S$525 per night from 3 Feb to 4 Feb
S$525
3 Feb - 4 Feb
includes taxes & fees
8/10 Very Good! (1,012 reviews)
The room was spacious, clean, and modern. The pools and pool areas were clean and maintained. The restaurants and cafe had really good food. The EV charging station was very convenient.

Reviewed on 21 Jan, 2026

Hawks Cay Resort
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard Marathon FL
Fully refundableReserve now, pay when you stay
The price is S$539 per night from 1 Feb to 2 Feb
S$539
1 Feb - 2 Feb
includes taxes & fees
9/10 Wonderful! (1,084 reviews)
Property was beautiful, room was clean but a little underwhelming compared to the resort we stayed at for a few days before during our trip to Key West. Our only and biggest complaint was that we opted to eat off property during our stay, after spending $48.00 for 2 coffees, muffins a bagel for breakfast ...

Reviewed on 24 Jan, 2026

Isla Bella Beach Resort & Spa
See all 8,411 properties in Florida Keys
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Mallory Square which includes a sunset and a bay or harbor as well as a large group of people

Mallory Square

4/5(36 reviews)

Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.

Mallory Square
Smathers Beach showing a sandy beach, a luxury hotel or resort and tropical scenes

Smathers Beach

4/5(10 reviews)

Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.

Smathers Beach
Southernmost Point featuring signage as well as a large group of people

Southernmost Point

4/5(39 reviews)

Snap a memorable photograph from the edge of North America at this monumental landmark.

Southernmost Point

What to do in Florida Keys

12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

S$35
per adult
92% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

S$58
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Key Largo Snorkeling Tour - rental mask, fins and vest INCLUDED

Key Largo Snorkeling Tour - rental mask, fins and vest INCLUDED

S$87
per adult
88% of travellers recommend
Key Largo Snorkeling Tour - rental mask, fins and vest INCLUDED
See all activities in Florida Keys

Frequently asked questions

Can I cancel my flight booking to Florida Keys due to COVID-19?
If you've yet to book your tickets, read the terms and conditions of the airfare you're considering. If you've already reserved your flight to Florida Keys, make use of our Customer Service Portal. The information here will help determine which COVID-19 policies apply to your booking and guide you with the next steps.
What's the best way to find cheap flights to Florida Keys that have flexible change policies?
We understand that things can change from one minute to the next, so booking a flexible ticket with Expedia is a sensible idea. Just tick the "No change fee" box directly under the "Flexible change policies" filter. Your low-cost, flexible flight to Florida Keys is just a few clicks away.
What are some of the general tips for travellers to Florida Keys during the COVID-19 outbreak?
The COVID-19 pandemic has brought about dramatic changes to the way we travel. If you're planning an escape to Florida Keys, the following tips will help you navigate these new rules and challenges:
  • Research what, if any, rules or restrictions apply to both your origin and destination. It may not be possible to travel depending on local circumstances, so be sure to check before you lock something in.
  • When you pass through airport screening, keep your face mask on. You will be asked to briefly lower it for identification purposes. Anyone refusing to wear a mask may be fined and denied entry.
  • Avoid handing your boarding pass directly to a TSA employee. Instead, position the pass on the reader and then hold it up to allow the agent to visually inspect it.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on luggage. This will have to be removed from your bag for screening.
  • Put any personal items (phone, wallet and keys) in your carry-on rather than a bin to minimize handling during screening.
  • Separate any food you have for X-ray screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA employee to touch and inspect your belongings.

Which airlines fly to Florida Keys?
Delta is a leading airline servicing Florida Keys. Search for airfares to Key West Intl. Airport (EYW) and you'll have 191 Delta flights each month to pick from.
How can I find cheap tickets to Florida Keys?
An effective strategy for scoring cheap airfares is to be flexible with your travel dates. Begin with searching for your flight to Florida Keys, then click on the "flexible dates" box to see prices for nearby days. Another helpful hint? Book well in advance. To give you an idea of fares, was the best price for a flight to Florida Keys in the last seven days.
How much is a flight to Florida Keys?
The cost of a round-trip journey to Florida Keys in the last seven days ranged between and . If you were travelling one way from (), you could have gotten a great deal from only .
What are the most popular airports to fly into in Florida Keys?
Start planning your Florida Keys escape by securing one of the 1119 flights each month to Key West Intl. Airport (EYW). This is the region's main entry point.
When is the cheapest time to fly to Florida Keys?
Jet off on a Tuesday to boost your odds of picking up the cheapest deal to Florida Keys. Mondays are usually the second most affordable day to depart. Saturday is normally the most expensive day to fly anywhere.
How much is a plane ticket to Florida Keys?
In the last seven days, ticket prices to Florida Keys varied from to .
Which airlines with flights to Florida Keys employ COVID-19 cleanliness policies?
As passengers begin travelling once again, most reputable airlines have introduced social distancing and other important measures to help lessen the spread of COVID-19. Here are some of them:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • Frontier Airlines - this airline is known for electrostatic cleaning and conducting passenger temperature checks.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.