Florida Keys Golf Vacations

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Flight and Golf hotel deals in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Northside Resort
CA $872
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,460 reviews)
Good

Reviewed on Sep 15, 2026

Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
CA $2,311
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,422 reviews)
Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal clear. Staff was friendly and accommodating. The roosters that roamed were the healthiest looking rooster I ever saw 😉. We wandered off the property but my observation was that you didn’t need to leave to stay busy and active, very self-contained.

Reviewed on Sep 14, 2026

Hawks Cay Resort

Hawks Cay Resort

CA $1,505
per person
Oct 21 - Oct 27
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Miami (MIA)
8.2/10 Very good! (1,006 reviews)
Beautiful resort

Reviewed on Sep 15, 2026

Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

CA $1,565
per person
Oct 21 - Oct 27
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Miami (MIA)
8.8/10 Excellent! (1,009 reviews)
The room was clean and the pools were excellent! But everything else was just average, and I don't know that I'd say it was worth a $50/day resort fee (what does this cover? Why not just put it in the room rate?) We stayed 4 nights and by the third night we had to ask to have someone come by and bring fresh towels. I'm used to seeing signs at hotels that state for environmental reasons they may only clean rooms every so often, but there was no such indication. Our room was off at the edge of the resort, by the fitness room which meant every time someone came in the building, the whole building shook when the door slammed behind them. So much for getting a nice sleep-in on vacation because this started at 5 or 6 am. I can definitely see the benefit to staying here with a larger group, families and friends staying in one of the villas. But as a couple, I probably wouldn't come back.

Reviewed on Sep 15, 2026

Eden House

Eden House

Key West Historic District
CA $1,374
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (1,003 reviews)
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5* Golf holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
CA $2,311
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,422 reviews)
Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal clear. Staff was friendly and accommodating. The roosters that roamed were the healthiest looking rooster I ever saw 😉. We wandered off the property but my observation was that you didn’t need to leave to stay busy and active, very self-contained.

Reviewed on Sep 14, 2026

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3 Night Golf holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Hawks Cay Resort

Hawks Cay Resort

CA $915
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
8.2/10 Very good! (1,006 reviews)
Beautiful resort

Reviewed on Sep 15, 2026

Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

CA $1,035
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
8.8/10 Excellent! (1,009 reviews)
The room was clean and the pools were excellent! But everything else was just average, and I don't know that I'd say it was worth a $50/day resort fee (what does this cover? Why not just put it in the room rate?) We stayed 4 nights and by the third night we had to ask to have someone come by and bring fresh towels. I'm used to seeing signs at hotels that state for environmental reasons they may only clean rooms every so often, but there was no such indication. Our room was off at the edge of the resort, by the fitness room which meant every time someone came in the building, the whole building shook when the door slammed behind them. So much for getting a nice sleep-in on vacation because this started at 5 or 6 am. I can definitely see the benefit to staying here with a larger group, families and friends staying in one of the villas. But as a couple, I probably wouldn't come back.

Reviewed on Sep 15, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $1,197
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip flight included
Austin (AUS) to Key West (EYW)
8.6/10 Excellent! (3,560 reviews)
Good first impression checking in. Staff was friendly and courteous. Room was ok off of the Tranquility pool. We did not like the heavy frosted sliding bathroom door, it was loud. There also needs to be counter space or cabinet of some sort in the bathroom. We brought a table in so we could put our toiletries on it. There should be another mirror somewhere in the room other than the one in the bathroom. Our light and fan was on some kind of timer and turned on and off automatically at random times. Turning on at 7 am was not cool. The beach was gross with all the sargassum and stunk really bad. We booked at this hotel due to being on the beach and we didn’t even go on it at all. The resort next door had really clean and usable beach. Not sure why ours was so bad. One of the pools is under construction. The bar off the beach was nice except for the smell. Food was good. Good reminder communications from the hotel on events and happenings at the pools. Overall, good food and drinks, friendly staff and easily accessible to the main streets.

Reviewed on Sep 15, 2026

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4 Night Golf holidays in Florida Keys

Price found within the past 48 hours. Click for updated prices.
Hawks Cay Resort

Hawks Cay Resort

CA $1,530
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very good! (1,006 reviews)
Beautiful resort

Reviewed on Sep 15, 2026

Heron House - Adult Only

Heron House - Adult Only

Old Town Key West
CA $1,533
per person
Oct 26 - Oct 30
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (1,158 reviews)
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Matecumbe
CA $2,311
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9.2/10 Wonderful! (1,422 reviews)
Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal clear. Staff was friendly and accommodating. The roosters that roamed were the healthiest looking rooster I ever saw 😉. We wandered off the property but my observation was that you didn’t need to leave to stay busy and active, very self-contained.

Reviewed on Sep 14, 2026

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See all available trips from Columbus to Florida Keys
View all trips

Discover the ultimate golf vacation from Florida Keys with Expedia

What are some benefits when booking golf vacations from Florida Keys?

Booking a golf vacation means putting golf at the centre of your entire experience. Not only will you be able to enjoy easy access to the greens, but you'll often have access to all the equipment you need as well. Plus, golf stays tend to be on the more luxurious end of the spectrum, so you're likely to have some other high-end amenities as well.

How can I find the best golf vacations in Florida Keys?

The best way to find golf vacations in Florida Keys is to take advantage of numerous search filters. You can look for golf stays specifically, with additional filters available for certain courses in some destinations. Plus, if you travel during the off-season in , you may even be able to get high-end stays at a discount.

Are there cheap golf packages available?

Yes, you'll find prices as low as CA $872, but the overall price depends on several factors. The time of year you travel to Florida Keys and the amenities you opt for can play a role in the cost of your package. Some package deals offer discounts of up to 20, but that's just a general trend rather than a guarantee.

Can I book golf and spa vacation packages?

Golf is often considered a luxury activity, so it's only natural that it be paired with other high-end experiences. You can implement the spa filter to sort for properties that have spa facilities, which can be especially useful for resting and rejuvenating in between games.

How can I find luxury golf vacations in Florida Keys?

A lot of golf vacations are already luxurious given the nature of the game, but there are a few things you can do to push it as far as it can go. Use search filters to highlight only 5-star properties to ensure you're getting the best of the best. Business-class flights are available as well in most cases.

Can I book an all-inclusive golf vacation in Florida Keys?

In many cases, yes. There's even a search filter for all-inclusivity, so you can sort for all-inclusive stays specifically. Even when an all-inclusive experience that matches your needs isn't available, you may be able to find some half-board options. This is also one of the best ways to find luxury golf vacations.

Why should I book golf packages including flights?

When you book your flight and your accommodations together, you can enjoy some serious savings compared to what you'd find booking separately. We're your one-stop shop for all your travel needs, and convenience is just the beginning when booking golf vacations from Florida Keys with us.

Should I book a last-minute golf vacation?

Booking last-minute to Florida Keys shouldn't be your first choice, but if you like to travel spontaneously, there are a few benefits to enjoy. Occasionally, you may be able to save money by booking last-minute, as accommodations are interested in filling their last few vacancies as fast as they can. The deals aren't guaranteed, however, so keep that in mind when planning. Sometimes, accommodations will simply be sold out.

Can I book a golf vacation that is fully refundable?

Yes, you'll find several options that are fully refundable among our packages in Florida Keys. You can even filter for fully refundable stays specifically. Just remember to check out each accommodation's policy specifically to make sure your booking qualifies.

Why should I book my golf trip with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel needs. You can search through a massive collection of packages and potentially unlock discounts by booking your flight and accommodations together. Even more discounts may be available for Expedia Rewards members, such as special deals and the ability to earn points to put toward discounts on future bookings.

Golf Hotels in Florida Keys

Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
  • 3 hours drive from Duval Street
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,440 reviews)
"Clean and comfortable rooms, but I did get a dated feel, but certainly served our purpose. The property supplied EVERYTHING needed to enjoy your stay. I didn’t have dinner there, but their breakfast was elevated and delish. The Adult pool we used had an exercise instructor, a spa and was crystal ..."

Reviewed on Sep 14, 2026

Cheeca Lodge & Spa
Pier House Resort & Spa

Pier House Resort & Spa

1 Duval St Key West FL
  • 11 min walk from Duval Street
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
Pier House Resort & Spa
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
  • 10 min walk from Duval Street
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (3,603 reviews)
"Good first impression checking in. Staff was friendly and courteous. Room was ok off of the Tranquility pool. We did not like the heavy frosted sliding bathroom door, it was loud. There also needs to be counter space or cabinet of some sort in the bathroom. We brought a table in so we could put our ..."

Reviewed on Sep 15, 2026

Southernmost Beach Resort and Guesthouses
See all 8,263 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.

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $59
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $77
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

CA $109
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
See all activities in Florida Keys

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.