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Florida Keys vacation rentals

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Top-rated vacation rentals in Florida Keys

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

SUPERHOST
  1. Entire condo
  2. Marathon
Tropical Paradise ~ The Reef Marathon, 2BR Villa!

The Reef at Marathon is situated right in the center of the Florida Keys within an exciting, family-oriented island community. Whether visiting to experience the world-class fishing opportunities or simply to lounge under the radiant Florida sunshine, you are sure to love your time at The Reef at Marathon! Each unit at The Reef at Marathon is a standalone villa that includes 2 BR/2 BA, private balcony, a full kitchen, and a washer & dryer. Free Wi-Fi, and parking.

$169 per night
SUPERHOST
  1. Entire guesthouse
  2. Key Largo
Bayside Cottage, beach, fishing pier & sunsets 😎

Cabin/Guesthouse, gardens; beach short two minutes walk, fishing pier, backyard sunsets, private and peaceful. Please; Treat our Cabin with the same love and respect as your own home, thank you. Adults only!!!!

$178 per night
SUPERHOST
  1. Entire condo
  2. Islamorada
Resort with Private Beach & Gorgeous Sunsets!

Private Beach at the Topsider Resort! This resort has 20 unique octagon stilt houses with fabulous amenities, and famous “T” shaped pier stretching out 180 feet into the bay. Onsite you will find a selection of exciting amenities, such as a heated swimming pool, a pristine private beach for relaxing, a cozy Jacuzzi, tennis and shuffleboard courts, bicycles and kayaks. Each Villa has 2 bedrooms and 2 bathrooms, FREE high-speed WIFI, a TV with cable in the family room, two parking spots.

$212 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Boats
  • Cottages

Florida Keys house rentals

  1. Entire home
  2. Key Largo
Ocean view house freekayaks and paddle board
$179 per night
  1. Entire home
  2. Key Largo
Casa Marina - heated pool, ramp & 70 ft of dock!
$178 per night
  1. Private room
  2. Florida City
Coral Cottage
$49 per night
SUPERHOST
  1. Entire home
  2. Key Largo
Key Largo Gem
$98 per night
  1. Entire home
  2. Marathon
NEW LISTING! Dog-Friendly, Oceanfront Home w/Private Pool and Hot Tub!
$252 per night
  1. Entire home
  2. Key Largo
New listing - Newly Renovated Private Single House
$110 per night
SUPERHOST
  1. Private room
  2. Key West
A Little Place in Key West
$156 per night
  1. Entire home
  2. Key Largo
Ocean-Inspired Key Largo Coconut Cottage
$120 per night
  1. Entire home
  2. Key Largo
Beautiful NEW Home in Key Largo Resort
$150 per night
  1. Entire home
  2. Key Largo
Heart & Soul of Key Largo. 2/1 house
$90 per night
SUPERHOST
  1. Entire home
  2. Key Colony Beach
Paradise Found! 3/2 Beach Club included
$240 per night
SUPERHOST
  1. Entire home
  2. Marathon
Waterfront Hideaway
$152 per night

Florida Keys beach vacation rentals

SUPERHOST
  1. Entire condo
  2. Key Colony Beach
Beachside Unit 39 Tiki Huts, Private Beach & Pool
$193 per night
  1. Entire serviced apartment
  2. Marathon
Sunset Villas, 1-bedroom suite w/ Full Kitchen
$129 per night
SUPERHOST
  1. Entire condo
  2. Key Colony Beach
Beachside Unit 14 -Tiki Huts, Beach, Pool...Oh My!
$193 per night
SUPERHOST
  1. Tiny home
  2. Key Largo
The Oasis in key largo with your own private beach
$250 per night
  1. Entire cottage
  2. Key Largo
Tip’Sea 🐢Turtle Beach House
$150 per night
  1. Private room
  2. Key Largo
Keys Escape! Near John Pennekamp National Marine Sanctuary, Pool, Free Parking!
$374 per night
SUPERHOST
  1. Entire home
  2. Key Colony Beach
ABeachBungalow-60’dock w/ access to pool and beach
$325 per night
  1. Entire guest suite
  2. Islamorada
Efficiency - Snorkel, Swim, Kayak
$138 per night
  1. Private room
  2. Key Largo
Sleeping Rm Private Ent w use of RV Park Bathroom
$100 per night
SUPERHOST
  1. Entire condo
  2. Key Colony Beach
Oceanfront Sunrise Condo Private Beach Heated Pool
$305 per night
SUPERHOST
  1. Entire condo
  2. Key Colony Beach
Beachside Unit 28 - Private Beach, Pool & Paradise
$189 per night
SUPERHOST
  1. Entire condo
  2. Key Colony Beach
Beachside Unit 37 - Come Relax on the Atlantic!
$193 per night

Florida Keys winter vacation rentals

SUPERHOST
  1. Entire guesthouse
  2. Key West
Pelican Cottage
$164 per night
SUPERHOST
  1. Private room
  2. Key West
Nuns Room, A single travelers delight!
$156 per night
SUPERHOST
  1. Entire condo
  2. Key West
WALK TO BEACH, MALLORY SQUARE, DUVAL STREET
$175 per night
SUPERHOST
  1. Entire rental unit
  2. Key Largo
Escape to the Seaside - Manta Cottage
$150 per night
SUPERHOST
  1. Entire condo
  2. Key West
Key West Studio a short walk from Higgs & Duval
$117 per night
SUPERHOST
  1. Entire cottage
  2. Key Largo
Charming Key Largo Cottage on the Water w/Kayaks!
$247 per night
SUPERHOST
  1. Entire cottage
  2. Key Largo
Key Largo Waterfront Home with Tiki & Boat Dock
$225 per night
SUPERHOST
  1. Entire condo
  2. Key Largo
Rest and Relax
$99 per night
SUPERHOST
  1. Entire condo
  2. Key Colony Beach
Beachside Unit 27 - The Beach is Calling You!
$173 per night
SUPERHOST
  1. Entire vacation home
  2. Key Largo
Waterfront, GROUND LEVEL, Awesome Sunsets!!!
$224 per night
SUPERHOST
  1. Entire condo
  2. Islamorada
Beautifully Updated Studio Apartment, Summer Sea Condo
$75 per night
  1. Entire rental unit
  2. Marathon
Deluxe King One Bedroom Suite
$207 per night

Your guide to Florida Keys

All About The Florida Keys

From vibrant Key West to the mysteriously named No Name Key, the Florida Keys offer historical intrigue and geographical wonder in a graceful archipelago, stretching out from the Everglades towards Havana. Postcard-worthy turquoise waters make the Keys a popular destination for sports fishing, scuba diving, and boating. If you fancy a more leisurely set of activities during your visit, boat rides in the tropical sun and snorkeling let you set your own pace for exploring the dazzling coral islands.

The strong culinary culture of the Keys is centered around fresh seafood, from mahi-mahi to snapper to blackfin tuna, alongside other edible delights, like Key lime pie on a stick. For those wanting to explore both land and sea, consider venturing into the Mel Fisher Maritime Heritage Museum or the Key West Shipwreck Treasure Museum, both of which are excellent forays into the impact the ocean has had on the history of these islands.


How do I get around Florida Keys?

There are multiple ways to get to the Florida Keys, the simplest being by plane. Several major airlines offer flights to Key West International Airport (EYW) on a daily basis. Alternative means of accessing the area include taking bus or shuttle services, driving to the Keys via the All-American Road, or even sailing your own boat. Once you’re there, the best way to get around is by biking. The region has many oceanside roads, and cycling along the cerulean waters is an experience in itself. Another means of transit is the local bus services. The area is served by five bus routes that traverse the majority of Key West, including its Old Town. There is also a shuttle service that connects the different islands.


When is the best time to stay in a vacation rental in Florida Keys?

The best time to look for Florida Keys vacation rentals is between March and May. There are typically fewer crowds during this time and the weather is still warm without being humid, unlike in the muggier summer months.. The islands also host a variety of events in the spring. The 7 Mile Bridge Run in April is an annual marathon spanning the entirety of one of the island’s bridges. The Taste of Key West, also in April, is an annual celebration of the various cuisines that call the archipelago home, and feature everything from fine dining to seafood shacks and food trucks. The Key West Songwriters’ Festival in May has been going strong for 25 years and features dozens of performers across genres such as country, reggae, and rock.


What are the top things to do in Florida Keys?

Duval Street

Duval Street, running from Mallory Square to the Southernmost Point marker, is one of Key West’s most lively streets. Host to museums, shops, galleries, and cafes, Duval Street is great not only for people-watching, with its many annual parades and events, but also for learning about the history of the Florida Keys, with attractions such as the Ernest Hemingway Home and Museum, and the former Strand Theater.

Dry Tortugas National Park

Dry Tortugas National Park, 70 miles from Key West, is only accessible by boat or plane, but is a worthwhile stop on any trip to the Florida Keys. An archipelago of seven beach-ringed islands, one is taken up entirely by the preserved ruins of Fort Jefferson, which stands guard over the coral, seagrass, and shipwrecks that welcome snorkelers from around the world. Popular snorkeling spots are the Historic Coaling Pier, Fort Jefferson's moat wall, and Garden Key. Boaters can explore around Loggerhead Key's Little Africa Reef and the Windjammer Wreck.

Marathon

Not to be confused with the activity, or the location of the same name in Greece, Marathon is the sportfishing center of the Florida Keys. Charters are easily arranged here for deep-sea, reef, and flats fishing. A variety of beaches and beachfront restaurants line the strip, while the former Seven Mile Bridge on the island makes a scenic path for walkers, joggers, and cyclists.