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Florida Keys Vacation Rentals

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Vacation Rentals in Florida Keys

Captain Pip's at Knight's Key Inn

Captain Pip's at Knight's Key Inn

3 out of 5
40 Kyle Way W, Marathon, FL
The price is CA $98 per night from Dec 8 to Dec 9

Situated in Marathon, this aparthotel is 0.1 mi (0.1 km) from Vaca Key and 2.4 mi (3.8 km) from Seven Mile Bridge. Pigeon Key Foundation and The Turtle Hospital ...

4.5/5Wonderful! (559 reviews)

"Overalls very good.....nice location... .............."…"

Reviewed on Nov. 21, 2020

Captain Pip's at Knight's Key Inn
Tropical Cottages

Tropical Cottages

3 out of 5
243 61st Street Gulf, Marathon, FL
The price is CA $98 per night from Dec 2 to Dec 3

Situated in Marathon, this cottage is 0.3 mi (0.5 km) from Crane Point Museum and Nature Center and 2.3 mi (3.7 km) from Sombrero Beach. Florida Keys Country ...

4/5Very Good! (144 reviews)

"I stayed in what appeared to be the original house (divided into 2 units). Classic old Florida, very "keysey"."…"

Reviewed on Nov. 24, 2020

Tropical Cottages
Skipjack Resort Suites & Marina

Skipjack Resort Suites & Marina

3 out of 5
19 Sombrero Blvd, Marathon, FL
The price is CA $154 per night from Dec 8 to Dec 9

Situated in Marathon, this golf aparthotel is 0.2 mi (0.2 km) from Florida Keys Country Club and 2.1 mi (3.5 km) from Sombrero Beach. Crane Point Museum and ...

4.2/5Excellent! (628 reviews)

"Lovely king suite- clean - served our visit to Marathon for three nights well! Maid service non existent due to covid but helpful staff brought us everything we needed when requested. ( Towels and amenities) Very close to some good restaurants and Publix ."…"

Reviewed on Nov. 8, 2020

Skipjack Resort Suites & Marina
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Riptide RV Resort

Riptide RV Resort

2 out of 5
97680 Overseas Hwy, Key Largo, FL

Situated in Key Largo, this beach campsite is 0.4 mi (0.6 km) from Bluefin Rock Harbor Marina and 3.1 mi (4.9 km) from John Pennekamp Coral Reef State Park. ...

4.2/5Excellent! (92 reviews)
Such a cute place!

"Easy, fun and clean experience"…"

Reviewed on Aug. 16, 2020

Riptide RV Resort
Bayside Townhomes and Boatslips

Bayside Townhomes and Boatslips

3.5 out of 5
81450 Overseas Highway, Islamorada, FL
The price is CA $298 per night from Dec 1 to Dec 2

Located in the heart of Islamorada, this beach condo is within a 10-minute walk of Hurricane Monument and Florida Keys Brewing Co.. Indian Key Historic State ...

4.6/5Wonderful! (187 reviews)
Wonderful stay

"We had a wonderful 6 night stay at the Islander Bayside Townhomes. We started on a very positive note when we received a phone call from the front desk 4 hours prior to our check-in time to let us know that our room was ready for us if we wished to check-in early. I am a seasoned traveler and I have ..."…"

Reviewed on Oct. 25, 2020

Bayside Townhomes and Boatslips
Ragged Edge Resort & Marina

Ragged Edge Resort & Marina

2.5 out of 5
243 Treasure Harbor Dr, Islamorada, FL
The price is CA $233 per night from Dec 3 to Dec 4

Situated near the beach, this aparthotel is 0.6 mi (0.9 km) from Founders Park and 2.3 mi (3.6 km) from Theater of the Sea. Windley Key Fossil Reef Geological ...

5/5Exceptional! (1 review)

"We have stayed at Ragged Edge before and had the two-bedroom, apartment style room. It is a large layout with lots of room in the kitchen and open den layout when you walk in. The bathrooms are also nicely updated and very clean. The units are kept up and have a "homey" feel to them. Not fancy, just ..."…"

Reviewed on Oct. 12, 2020

Ragged Edge Resort & Marina
The Reef at Marathon by Capital Vacations

The Reef at Marathon by Capital Vacations

3 out of 5
6800 Overseas Hwy, Marathon, FL

Located in the heart of Marathon, this condo is 0.6 mi (1 km) from Crane Point Museum and Nature Center and 2.6 mi (4.2 km) from Sombrero Beach. Florida Keys ...

4.5/5Wonderful! (64 reviews)

"Lots of space, beautiful grounds, easy to get to, clean!"…"

Reviewed on Oct. 19, 2020

The Reef at Marathon by Capital Vacations
Topsider Resort by Capital Vacations

Topsider Resort by Capital Vacations

3.5 out of 5
75500 Overseas Hwy, Islamorada, FL

Nestled on the beach, this Islamorada condo is within 3 mi (5 km) of San Pedro Underwater Archaeological Preserve State Park, Anne's Beach and Indian Key Historic ...

4.5/5Wonderful! (18 reviews)

"Beautiful resort, right in the bay. Beautiful views!"…"

Reviewed on Nov. 20, 2020

Topsider Resort by Capital Vacations
Waterfront Cottage in Key Largo

Waterfront Cottage in Key Largo

999 Morris Ave, 618, Key Largo, FL

Situated in Key Largo, this romantic holiday home is within 9 miles (15 km) of Key Largo Baptist Church, John Pennekamp Coral Reef State Park and Christ of the ...

5/5Exceptional! (5 reviews)
Manatee Bay

"Thoroughly enjoyed our stay and will definitely rebook in the future! The unit was clean, well organized and included everything that we needed to get settled in and immediately begging enjoying our vacation."…"

Reviewed on Sep. 24, 2020

Waterfront Cottage in Key Largo
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy, Islamorada, FL

Nestled on the beach, this Islamorada villa is 0.3 mi (0.6 km) from History of Diving Museum and 2 mi (3.2 km) from Theater of the Sea. Florida Keys Brewing ...

The Islands of Islamorada
Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club

3 out of 5
107800 Overseas Hwy, Key Largo, FL
The price is CA $208 per night from Dec 9 to Dec 10

Situated on the waterfront, this condominium resort is 0.8 mi (1.3 km) from John Pennekamp Coral Reef State Park, and within 6 mi (10 km) of MarineLab Undersea ...

4/5Very Good! (137 reviews)

"A very good stay"…"

Reviewed on Mar. 9, 2020

Anchorage Resort & Yacht Club
Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina

2 out of 5
38801 Overseas Highway, Big Pine Key, FL

Nestled on the beach, this Big Pine Key campsite is within a 10-minute walk of Bahia Honda State Park and Sandspur Beach. Loggerhead Beach is 2.2 mi (3.6 km) ...

4.2/5Excellent! (68 reviews)

"We loved everything about this little paradise, we can't wait to go back"…"

Reviewed on Jul. 14, 2020

Sunshine Key RV Resort & Marina
Mariner's Club Key Largo by KeysCaribbean

Mariner's Club Key Largo by KeysCaribbean

3.5 out of 5
97501 Overseas Hwy, Key Largo, FL

Situated by the sea, this condominium resort is 0.3 mi (0.5 km) from Bluefin Rock Harbor Marina and 2.1 mi (3.3 km) from Dolphins Plus. John Pennekamp Coral ...

3.9/5Good! (375 reviews)

"This property is a bunch of town homes that are fairly well maintained looking. We were a little disappointed that there was nowhere to eat on the property originally, but there's plenty of places to eat in Key Largo and the surrounding areas."…"

Reviewed on Feb. 10, 2020

Mariner's Club Key Largo by KeysCaribbean
Old Wooden Bridge Marina

Old Wooden Bridge Marina

2.5 out of 5
1791 Bogie Drive, Big Pine Key, FL
The price is CA $187 per night from Nov 28 to Nov 29

Located in Punta Brisa, this cottage is 0.4 mi (0.7 km) from No Name Key and 2.4 mi (3.9 km) from National Key Deer Refuge Visitor Center. Florida Keys Wilderness ...

3.9/5Very Good! (35 reviews)

"Loved the beautiful sunrise and quiet area. Not a fan of the septic stench."…"

Reviewed on Oct. 23, 2020

Old Wooden Bridge Marina
Welcome to Paradise!

Welcome to Paradise!

1530 Ocean Bay Drive, # 208, Key Largo, FL

Situated in Key Largo, this condo is 0.5 mi (0.8 km) from Dolphins Plus and 2.4 mi (3.9 km) from John Pennekamp Coral Reef State Park. Bluefin Rock Harbor Marina ...

4.8/5Exceptional! (13 reviews)
Perfect Tropical getaway

"This condo was steps above others we've stayed in. It was clean and tidy with every amenity we needed and then some. There were plush towels and several types of pillows. It has kitchen gadgets galor including a powerful blender for top notch margaritas. It's within walking distance of Key Largo ..."…"

Reviewed on Sep. 20, 2020

Welcome to Paradise!
Angler's Reef Resort by KeysCaribbean

Angler's Reef Resort by KeysCaribbean

3.5 out of 5
84977 Overseas Highway, MM 84.9, Islamorada, FL

Nestled on the beach, this Islamorada holiday home is within a 10-minute walk of Windley Key Fossil Reef Geological State Park and Theater of the Sea. Founders ...

4.6/5Wonderful! (10 reviews)
Beautiful but missing a few things.

"The condo is beautiful and the property/pool were a good location. The things that we felt were not 100% were there was no extra towels for showering. Four for 3 people for nine days. There were no extra blankets foe the beds and it was very cold a couple of nights (heat was out but it did get fixed) ..."…"

Reviewed on Mar. 20, 2020

Angler's Reef Resort by KeysCaribbean
Bay Breeze Houseboat Getaway

Bay Breeze Houseboat Getaway

Key Largo, FL
The price is CA $260 per night from Dec 5 to Dec 6

Located in Key Largo Village, this romantic houseboat is within a 15-minute walk of John Pennekamp Coral Reef State Park and Dolphins Plus Bayside. Key Largo ...

Bay Breeze Houseboat Getaway
Crewed Cruising on 62' 1400 sq ft Houseboat Motor Yacht - Wheelchair Accessible

Crewed Cruising on 62' 1400 sq ft Houseboat Motor Yacht - Wheelchair Accessible

225 Upper Matecumbe Road, Key Largo, FL

Located in Sexton Cove Estates, this historic houseboat is within a 15-minute walk of Key Largo Baptist Church and John Pennekamp Coral Reef State Park. Christ ...

Crewed Cruising on 62' 1400 sq ft Houseboat Motor Yacht - Wheelchair Accessible
Indigo Reef Resort Villas & Marina by KeysCaribbean

Indigo Reef Resort Villas & Marina by KeysCaribbean

3.5 out of 5
11600 1st Avenue Gulf, Marathon, FL

Situated on the waterfront, this condo is steps away from Florida Keys Aquarium Encounters and Captain Hooks Marina and Dive Center. Island Hoppers Aerial Adventures ...

4.5/5Wonderful! (43 reviews)
Cumbersome, but nice.

"We had to move from one unit to the next mid vacation due to ,either, vrbo, or coral reef making an error, in which they gave us a lodging unit which was not abailable for the entire period of our vacation. We received a modest discount for our inconvenience, having to move all of our stuff and boat ..."…"

Reviewed on Sep. 14, 2020

Indigo Reef Resort Villas & Marina by KeysCaribbean
Serenity AT Sea! Leave ALL Your Worries Behind!!!

Serenity AT Sea! Leave ALL Your Worries Behind!!!

299 Morris Ave, Key Largo, FL

Situated in Key Largo, this houseboat is within 9 miles (15 km) of Key Largo Baptist Church, John Pennekamp Coral Reef State Park and Upper Sound Point. Key ...

4.5/5Wonderful! (2 reviews)
The Best but not for the fancy nor faint of heart

"You get to stay on the water in a secluded area!!! I absolutely loved it, and it was probably one of my favorite vacations!!! :-). But it’s also camping on the water mostly without running water, and AC only through a generator that only lasts about 7 hours total before you have to put more gas in ..."…"

Reviewed on Nov. 10, 2020

Serenity AT Sea! Leave ALL Your Worries Behind!!!
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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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Florida Keys. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Other types of properties in Florida Keys you may be interested in

Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys

2.5 out of 5
13201 Overseas Hwy, Marathon, FL
Free cancellationReserve now, pay when you stay
The price is CA $165 per night from Nov 29 to Nov 30
Fairfield Inn & Suites by Marriott Marathon Florida Keys
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy, Key Largo, FL
Free cancellationReserve now, pay when you stay
The price is CA $178 per night from Dec 16 to Dec 17
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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.