Book Direct & Save - No Booking Fees

Florida Keys Vacation Rentals

(572 rentals)
Days in the Florida Keys are spent on the water — diving the reef off Key Largo, chasing tarpon out of Islamorada, or walking down to the dock behind the house. Vacation rentals commonly have docks on canals, though there are some beaches within driving distance in each major area. Expect to pay a median of $388 a night for a vacation house or $290 a night for a condo.
Median nightly
$439
half of rentals cost less
Cheapest area
$306
Key Largo median
Best value month
September
warm water, low rates
Peak season
Jan-Mar
priciest

Where to stay in the Florida Keys

Map of Monroe County vacation rental areas
FLORIDA KEYS
The Lower Keys
Rental areas in the Florida Keys, from the mainland southwest: Key Largo, Islamorada, Marathon, the Lower Keys and Key West. Geometry from US Census TIGER/Line, public domain.
Key Largo →
The closest island to the mainland, Key Largo is known for its diving. It offers shallow coral reefs and deeper shipwrecks, great for both snorkeling and scuba diving.
55 rentals · from $85 · MIA 60–70 min
Islamorada →
Although it’s best for sport fishing, especially in the backcountry flats, a weekend stay typically won't work here. The village sets a seven-day minimum outside its tourist commercial district.
113 rentals · from $93 · MIA 90–100 min
Marathon →
In the middle of the keys, this is a good homebase if you want to explore both ends. Kids get the Turtle Hospital at MM 48.5 and the Dolphin Research Center at MM 59 on Grassy Key. Marathon’s code sets a seven-day minimum.
128 rentals · from $148 · EYW 60–70 min
The Lower Keys
Big Pine Key, Summerland Key, and Cudjoe Key sit past the Seven Mile Bridge, and more of their houses come with a dock than anywhere else in the chain. Key deer wander Big Pine, and boats run out to Looe Key, the reef named for a British frigate wrecked there in 1744.
EYW 40–45 min
Key West →
A walkable cultural area, Old Town has several attractions and nightlife, including the nightly sunset celebration at Mallory Square. Expect a condo or a cottage rather than a canal home.
71 rentals · from $133 · EYW 10–15 min
Tavernier Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Ocean-View | Family-Friendly | Resort Amenities | Tavernier / Upper KeysProperty Overview Welcome to Coastal Ways Suite at Ocean Pointe, a beautifully appointed 900 sq ft, 2-bedroom ocean-view condo in the Upper Florida Keys. Nestled between Key Largo and Islamorada, this resort-style retreat offers...

View all property information

Featured review

"Loved ocean Point unit 3210"

Unit was nicely updated and exactly as advertised. The unit was nicely appointed including the kitchen. Close to pool and tennis courts. Loved the beach! We will be back!

See all reviews

$266
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 5 miles to Anne's Beach

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Enjoy the sunrise from the balcony or from the condo through 50' of glass sliding doors. You can also view the sunset from our walkway on bayside. We have a full kitchen, dishwasher to microwave, washer/dryer, even beach towels. We have wifi,cable TV in living area and all bedrooms, master bath...

View all property information

Featured review

"Keys Condo"

Awesome peaceful location,clean and perfect amenities lots of birds and fish at marina manatee, sand sharks ,etc

See all reviews

$288
avg per night
Tavernier House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Swim. Sleep. Repeat., at Manatee Manor. This 3-bedroom, 2.5-bath home on Plantation Key has something for everyone. Enjoy a drink by the tiki bar, rack ‘em up at the billiard table, or soak up some vitamin D next to the pool. With an entrance just off the carport, the downstairs offers a comfortable...

View all property information

$303
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 3 miles to John Pennekamp State Park

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy the panoramic view this tropically decorated, fifth-story unit has to offer of the Atlantic Ocean and the adjacent Wildlife Sanctuary. The unit affords its guests the spectacular sunsets the Florida Keys are famous for, right from your balcony and living room.Kawama Yacht Club is situated at...

View all property information

Featured review

"Boys week"

Great atmosphere, two minutes to the Atlantic. Jose great host, very clean. Thank you Jose for sharing your home.

See all reviews

$294
avg per night
Islamorada Villa
Sleeps 14, 5 bedrooms, 4 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

⭐ 5 bedroom 4 bathrooms (One bathroom by pool) ⭐ Canal home in Venetian Shores with access to bay and ocean ⭐ 100 foot of dockage on 100 foot wide deep canal. Ask about bringing your own boat ⭐ Location of canal is off Snake Creek near MM86 ⭐ Beautiful large pool with hot tub in tropical...

View all property information

$519
avg per night

Why Choose FloridaRentals.com?

No booking or service fees

No Booking or Service Fees

Save up to 25% compared to other websites - no hidden costs.

Connect Directly with Hosts

Connect Directly with Hosts

Book with confidence and get the best rates.

Florida's #1 vacation rental listings site

Florida's #1 Vacation Rental Site

Trusted by millions - your go-to for the perfect Florida getaway.

Plantation Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Property #27839 - silverEscape to your own Keys hideaway with cozy island‑inspired home, coastal décor and a bright open living/kitchen area that flows onto a huge screened terrace. Relax in your own private pool, tiki hut-gazebo, shaded lounge areas and serene canal views, perfect for lazy mornings,...

View all property information

$400
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo...

View all property information

Featured review

"warm retreat"

Bay Harbor was delightful, from the condo unit to the grounds and amenities. We used the hot tub, exercise room and swimming pool, When we left there was 76 degrees, returned to 20 degrees in Pennsylvania.

See all reviews

$391
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 6.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Gulf-Front Modern Luxury | 5BR w/ Rooftop Deck, Infinity Pool, Dock & More! Indulge in an unparalleled luxury experience in this breathtaking 5-bedroom, 5.5-bathroom estate in Marathon, Florida. With direct Gulf views, high-end amenities, and a sleek modern design, this home is a dream getaway for...

View all property information

Featured review

"AWESOME BAYSIDE OCEAN LOCATION, PROPERTY AND STUNNING HOME - MARCH/APRIL 2026"

The ocean view from the roof and 5 bedroom modern style home is 2nd to none in the keys! Each bedroom has it's own bathroom and the home is very modern and in excellent condition. The infinity pool is...

See all reviews

$1,437
avg per night
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Upon entering the home you’ll be greeted by laidback island decor and vast ocean views. The Tommy Bahama Tiki inspired apartment, over looking the marina located in the 5th building, offers two bedrooms and two bathrooms, Free Parking, High-Speed WiFi, Fully equipped kitchen- Washer and dryer. Self...

View all property information

$275
avg per night
Big Pine Key House
Sleeps 9, 3 bedrooms, 2.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Sunrise Drive, the perfect 3 bedroom, 3 bath home for your stay in the Keys. It’s located in Tropical Estates, a quiet upper scale community with water access throughout. A perfect location if you are looking for a tranquil island setting but close to the fun as Key West is just 25 miles south....

View all property information

Featured review

"Beautiful peaceful!"

I was lucky enough to stay here December and part of January! EXCELLENT owners. AWESOME pool area and a WONDERFUL comfortable home!!! Has everything you need and then some! It is close to Key West and...

See all reviews

$200
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

This rental offers beautiful Bonefish Bay views, private boat access, and everything you need for the perfect Marathon getaway. The home features a fully furnished kitchen, large living area, spacious balcony with open-water views, four bedrooms, three bathrooms, a laundry room, and comfortable sleeping...

View all property information

Featured review

"Lovely home"

This property is beautiful. The views are great, and the beds are comfy. We enjoyed our stay here. The kayaks were a nice bonus as well! The only downside is guest experience. There is no bulk shampoo,...

See all reviews

$496
avg per night
Key West House
Sleeps 10, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Island Dreaming – Your Luxury Key West Getaway - MONTHLY RENTAL Welcome to Paradise*** Please note for 2027 High Season rentals Jan- February - Arrival after the 5th of January for 6 week minimum is required in order to get accurate pricing***Discover the ultimate island retreat at Island...

View all property information

$639
avg per night
Key Largo House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to your dream coastal escape! A peaceful and beautifully well maintained home where comfort meets adventure. Beautiful 3-story canal-front home, just 3 houses from the ocean. Boaters Dream!! Including an entertainment room, ideal for an executive office or a private guest retreat with sofa bed....

View all property information

$325
avg per night
Islamorada House
Sleeps 10, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to One Ten Palms!Escape to paradise at this private oceanfront estate in Islamorada, where the laid-back spirit of the Keys meets resort-style comfort. Set on more than two acres of lush tropical grounds, the property is graced with 110 swaying palms and 250 feet of natural oceanfront beach,...

View all property information

$1,324
avg per night
Little Torch Key House
Sleeps 8, 3 bedrooms, 3 bathrooms
10 reviews

Distance to beach: 10 miles to Bahia Honda

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Paradise awaits in the Lower Keys! Situated on a large corner lot, you have over 200 feet of concrete dockage so BIG BOATS are welcome! Featured on " American Dream Home," this vacation home will not disappoint. Whether you're looking to fish the Atlantic or Gulf, snorkel at Looe Key Reef,...

View all property information

Featured review

"Vacation Getaway"

This home was absolutely beautiful! My husband and I, along with his family, stayed here and it accommodated 6 adults, 1 teen, a baby, and even our dog—everyone was perfectly comfortable. We loved relaxing...

See all reviews

$392
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
13 reviews

Distance to beach: 4 miles to Anne's Beach

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy the sunrise from the balcony or from in the condo through 50 ft of glass sliding doors. You can also see the sunset from our walkway on bayside. We have a full kitchen from dishwasher to microwave, washer/dryer, even beach towels. We have wifi, cable TV, and a Master Bath with whirlpool tub,...

View all property information

Featured review

"Excellent location, wonderful ocean view with full sunrises, clean and well-equipped condo with large balcony."

Condo was well equipped and tastefully decorated in an appropriate style. Direct ocean views from a 50' balcony overlooking docked boots with the occasional manatee swimming by was exceptional. Location...

See all reviews

$288
avg per night
Key Largo Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool

About this property

Welcome to our little slice of paradise! Your perfect Key Largo escape in the exclusive Landings of Largo community! This spacious and beautifully appointed 4-bedroom, 3-bathroom corner unit offers the ultimate blend of comfort, convenience, and resort-style amenities—ideal for families, groups,...

View all property information

Featured review

"Perfect large and roomy condo"

I can't express how much we love this condo at the Landings at Largo. The community is fantastic and so friendly. The pickleball court and pool are steps away and the pool is temperature-controlled. Our...

See all reviews

$318
avg per night
Tavernier House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • WiFi

About this property

Welcome to Ananda Shala!Nestled at Mile Marker 92 in Tavernier, this beautifully appointed 3-bedroom, 3-bath bayfront retreat invites you to slow down from the moment you arrive. Inspired by the spirit of a “shala”—a space for practice, reflection, and mindful living—this home...

View all property information

$368
avg per night
Key West House
Sleeps 10, 4 bedrooms, 3 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny...

View all property information

Featured review

"The Perfect Home"

I came to this house with friends, completely unsure what to expect from Key West. The island itself moves at this fascinating, slightly calm/chaotic pace, but stepping into this rental felt like entering...

See all reviews

$907
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 4 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Welcome to The Butterfly Cottage – Where Nature's Magic Meets Keys ComfortEscape to a truly unique Florida Keys experience at our certified Monarch Butterfly Garden sanctuary! This charming traditional conch cottage offers families a peaceful retreat where butterflies dance through native...

View all property information

$239
avg per night
New
Special Offer
Big Pine Key House
Sleeps 5, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Beautifully updated for your stay. This is not your typical vacation rental home, everything is new and curated for a wonderful stay. Conveniently located on deep water for Gulf or Atlantic access, no low bridges to navigate, with a natural preserve across the canal for privacy. Get ready to relax in...

View all property information

Featured review

"Big pine key paradise"

We absolutely loved our stay! The house was so cozy, clean, bright, and peaceful, and it had everything we needed to feel right at home. One of our favorite parts was enjoying our morning coffee on the...

See all reviews

$251
avg per night
Islamorada House
Sleeps 14, 6 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to Caribee Beach House!Discover the enchanting charm of Caribee Beach House, where the timeless allure of old-school Islamorada beautifully melds with stylish comforts. Tucked away in the heart of downtown Islamorada, this hidden gem offers an extraordinary retreat with 200 feet of private...

View all property information

$2,252
avg per night
Cudjoe Key House
Sleeps 6, 2 bedrooms, 3 bathrooms
55 reviews

Distance to beach: 15 miles to Bahia Honda

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This luxurious home overlooking Cudjoe Bay on the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with 11 total homes. This is #111 and I also rent 109 and 107 in case you need more than one. We are 40 feet from the water's edge facing Southwest. Lounge...

View all property information

Featured review

"Nice Condo"

Well kept clean condo and good host. The host has a nice binder with information and local things to do with mile markers. I would have liked to have the list emailed to me before we came to plan more...

See all reviews

$513
avg per night
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

SEAS THE DAY—or do absolutely nothing at all. You’re officially on island time.Welcome to your oceanfront retreat at Ocean Pointe Suites, where serene Atlantic views, coastal luxury, and resort-style amenities come together for the ultimate Florida Keys escape. Perfect for couples, friends,...

View all property information

$295
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 1 bathroom
2 reviews

Distance to beach: 0.8 miles to Fort Zachary Taylor State Park and Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Due to a change in licensing we are only available for monthly rentals. However I will consider offering a last minute deal pay for 3 and stay for 4. Please contact me directly.Here in Key West we believe in One Human Family where everyone is welcome and treated like family.Our condo has always...

View all property information

Featured review

"KWTrip"

Top notch place in great location. Very clean. Would definitely stay in this unit again sometime in the future.

See all reviews

$395
avg per night
Tavernier House
Sleeps 11, 4 bedrooms, 3 bathrooms

Distance to beach: 4 miles to Founders Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Coral Key!Discover a refined yet relaxed waterfront retreat in the heart of Plantation Key at Mile Marker 90. Thoughtfully designed for comfort, relaxation, and effortless entertaining, this spacious home offers everything you need for a memorable Florida Keys escape.Upon entering,...

View all property information

$593
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Mother Ocean!This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room...

View all property information

$455
avg per night
Tavernier Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

You'll find coastal comfort in our oceanfront condo at Ocean Pointe Suites in Key Largo, located directly on the Atlantic. Situated on 60 lush acres, Ocean Pointe offers a newly renovated pool and jacuzzi, private lagoon beach, outdoor grills, marina, boat ramp, pier, tennis, nature trails, swings...

View all property information

$242
avg per night
Tavernier Apartment
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Simply relax in this One bedroom One bathroom Oceanfront Condo at Ocean Pointe Suites in Tavernier.The comforting living room features a FLAT SCREEN TV, comfy pull out QUEEN SLEEPER SOFA and sliding glass doors that open to the step-out lanai offering sweeping views of the Atlantic.Visit delicious...

View all property information

$250
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2.5 bathrooms
3 reviews

Distance to beach: 0.5 miles to Higg's Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Private Luxury Key West Home with Private Pool, surrounded by lush tropical landscaping in the Casa Marina neighborhood of Old Town.The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district...

View all property information

Featured review

"Stunning Private Villa in Key West - Fabulous Location!"

We were so impressed with this Key West hidden gem. Along with it's beauty, you feel the love and care the owners have for this private home, as they provided you with all the amenities, plus so much more....

See all reviews

$451
avg per night
Tavernier House
Sleeps 14, 6 bedrooms, 4 bathrooms

Distance to beach: 1 miles to Founders Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Morada Breeze! This 6-bedroom, 4-bath bayside slice of paradise is ready to make your next vacation an enjoyable one. Located on Plantation Key in Islamorada, Morada Breeze has the amenities to elevate your trip to the Keys.Step inside to discover an expansive kitchen perfect for preparing...

View all property information

$550
avg per night
Key West Townhome
Sleeps 4, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Key West Getaway in Old Town!In the heart of Old Town, Southard Square Condominiums is an award-winning condo development with stunning gardens, a clubhouse with changing rooms/baths, seating area, kitchenette and one of the largest private community swimming pools in Key West. Staying...

View all property information

Featured review

"Beautiful home"

Thank you for you help in researching a vacation rental . We love key west an we will be inquiring with you in the future

See all reviews

$300
avg per night
Big Pine Key House
Sleeps 4, 2 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to Your Canal-Front Keys RetreatTucked away on Big Pine Key, this elevated canal-front home offers the relaxed rhythm of the Florida Keys with room to breathe, unwind, and reconnect with nature. From peaceful mornings on the deck to spectacular sunsets over the water, this home is designed...

View all property information

$189
avg per night
Big Pine Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Discover your own private escape with this beautiful canal-front home, perfectly positioned for those who love nature, boating, and peaceful coastal living. Backcountry & Ocean Access Enjoy direct canal access leading to incredible backcountry waters ideal for kayaking, paddleboarding, and world-class...

View all property information

$309
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 1.5 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Look no further than this perfect place in the Keys for your next vacation! Our cozy condominium provides an ideal location to enjoy the best of the Florida Keys and has some of the best views in all of Key Largo!Located on the 5th floor, you are the top floor of the building with no one above to...

View all property information

Featured review

"Beautiful view"

Location of condo was excellent. Very nice condo complex . Condo was very nicely decorated and had the best washer/dryer and comfy reclining couch. We wouldn't hesitate to return especially if you are going...

See all reviews

$278
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This condo is located in a tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yacht Club. FYC is a private 70-unit, gated community with a 53-slip marina and accommodations available for that tranquil tropical getaway you've always imagined. This condo offers...

View all property information

Featured review

"Location"

We have been searching for a unit in this area and found this. Islamorada has many restaurants, from fast food to white tablecloths, from waterfront dining to sports bars.

See all reviews

$205
avg per night
Cudjoe Key House
Sleeps 6, 2 bedrooms, 3 bathrooms
49 reviews

Distance to beach: 15 miles to Bahia Honda

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This luxurious home overlooking Cudjoe Bay on the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with 11 total homes. This is #109 and I also rent 111 and 107 in case you need more than one. We are 90 feet from the water's edge facing Southwest. Lounge...

View all property information

Featured review

"Don't worry be happy!!!"

Great location, views were gorgeous from our waterfront decks, 30 mins. to airport! Rental was clean, comfortable & well equipped with everything you need & then some. Home owners thought of everything...

See all reviews

$465
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Villa Sombrero – Private Waterfront Living with Sunset Views in the Florida KeysVilla Sombrero is a peaceful waterfront retreat overlooking Boot Key Harbor, offering breathtaking sunsets to the west and refreshing island breezes flowing in from the east through Sisters Creek. A natural waterway...

View all property information

Featured review

"Nice comfortable place..... Quiet except for construction work going on across the street."

It's the little things...... We had to call concerning changing the water filter on the refrigerator. The pool needed water added so that the filter and heater would work. The strainer was full of debris.......

See all reviews

$656
avg per night
New
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Escape to the heart of the Middle Florida Keys and experience laid-back island living at its finest in this beautifully appointed 3-bedroom, 2-bathroom waterfront retreat. Perfectly designed for families, couples, or boating enthusiasts, this inviting home combines comfort, convenience, and exceptional...

View all property information

$371
avg per night
Big Pine Key House
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Escape to paradise in this beautiful newly remodeled 2 bedroom 1 bath duplex unit on a canal nestled in the heart of Big Pine Key. Perfectly located near a grocery store, great local restaurants, parks, and just minutes from the famous Bahia Honda State Park. Whether you're looking to relax or head...

View all property information

$131
avg per night
Key West House
Sleeps 8, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • WiFi

About this property

The welcoming views at Coral Cove are waiting for you! This brand new two-bedroom, two-bathroom home is located on the open water and canal on Saddlebunch Key, just a stone’s throw from the famous “Baby’s Coffee.” You’re at Milemarker 15 and Key West is just minutes away!This...

View all property information

$230
avg per night
Key West Condo
Sleeps 5, 2 bedrooms, 1 bathroom
6 reviews

Distance to beach: 0.2 miles to Fort Zachary Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

AMAZING LOCATION in TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! She's not too shabby after all, she is close to the action, but far enough from the riff-raff :) Large front yard and porch to watch Key West pass by. Beautiful and spacious in/outdoors. POOL within...

View all property information

Featured review

"Shabby Chicken was perfect"

Shabby Chicken was absolutely perfect. From the location, amenities, interior , exterior, proximity to Truman waterfront , Fort Zachary beach and the Green Parrot. Marie (and Tom) were awesome. Karen and...

See all reviews

$398
avg per night
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Located in the first of Ocean Pointe Resort's five buildings, Coastal Retreat offers peaceful views of the protected mangrove preserve with glimpses of the Atlantic Ocean from the living room and private balcony. This thoughtfully renovated 915 sq. ft. corner condo is designed to provide a relaxing...

View all property information

Featured review

"Summer Stay"

My family and I loved our stay here. Great location, super clean, and comfortable. The amenities were great, really liked the decor. Highly recommend if you are looking for a stay in the area.

See all reviews

$310
avg per night
Key Largo House
Sleeps 4, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Stilt home on canal providing quick Bay access. Spacious master bedroom and bath. Bright and sunny kitchen and living area. Huge sundeck overlooking canal for ultimate relaxation. Covered patio underneath home, complete with picnic table, BBQ, hammock, outdoor games, and covered parking.Fenced in...

View all property information

Featured review

"Outstanding rental experience"

I rented this home for three months during the winter/spring and had an incredibly positive experience. The location is excellent- quiet at night but also close to fun bars and restaurants. The house is...

See all reviews

$189
avg per night
New
Key Colony Beach House
Sleeps 10, 5 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Experience the best of Florida Keys living at Marin, a beautifully renovated 4-bedroom, 3-bath waterfront retreat in Marathon's prestigious Key Colony Beach community. Located just two hours south of Miami and one hour north of Key West, this boater's paradise offers direct ocean access, a private...

View all property information

$714
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Open concept meets modern elegance in this stunning canal-front pool home located on sought after Coco Plum in the heart of the Florida Keys. No detail has been spared, from its spacious design to its functionality and huge outdoor living space, this home is sure to be your dream vacation location! Dedicated...

View all property information

$400
avg per night
Key Largo House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your ideal getaway in Key Colony Beach, FL! This charming 2-bedroom, 2-bathroom half duplex is brand new to the vacation rental market and offers everything you need for a relaxing and unforgettable stay. With deep water dockage, you’ll have easy access to the sparkling waters of the...

View all property information

$250
avg per night
Marathon Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Direct oceanfront condo with stunning views of the Atlantic. Large heated pool, tennis, hi speed wifi. Stroll along the long span of beach or relax at the oceanfront pool. Or just sit on your private balcony and watch the world go by. Large open living area, master bedroom with King size bed, the guest...

View all property information

Featured review

"Slice of Heaven"

The condo well appointed with everything you would need for your stay. The pool beautiful and warm, unfortunately the railing on the stairs of the shallow end make it difficult for an adult to get in or...

See all reviews

$291
avg per night
Key Colony Beach House
Sleeps 5, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Adorable 2 bedroom, 1.5 bathroom half duplex. Conveniently located at the top of 4th Street in exclusive Key Colony Beach. Nicely updated, fresh and bright! Walk to the Cabana Club and enjoy the complimentary membership with a large swimming pool, bar/restaurant, beautiful sandy beach. Excellent deep...

View all property information

$221
avg per night
Summerland Key Bungalow
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

This super cozy, comfortable 2-bedroom, 2-bath vacation rental is located in the heart of Cudjoe Key, just minutes from the open ocean. Perfect for fishing, snorkeling, and diving enthusiasts, the home boasts easy access to some of the best spots in the Florida Keys.Relax and unwind in style after...

View all property information

$164
avg per night
Full map
Map

Which part of the Keys fits your trip?

AreaMedian/nightBest forThe beach
Key Largo $306Divers, snorkelersNo natural sand this far north, though there’s Harry Harris Park's protected swimming area
Key West $395Walking to dinner, live music, cultureFort Zachary Taylor, rocky enough for water shoes; Smathers, long and manmade
Marathon $442Families with young kids, and anyone who wants a poolSombrero Beach, sand trucked in and kept up since the 1970s
Islamorada $477Sport fishing in the backcountry flatsAnne's Beach, shallow and calm
The Lower Keys N/ABoats, docks, snorkeling, quiet nightsBahia Honda is a protected tropical island

When to visit the Florida Keys

Winter is the Keys' busy season, and Fantasy Fest was invented in 1979 to liven up a quiet Key West October. Summer is the slower season, so you might find deals between June and August. No month here is cold, with Key West air highs running 75° in January and 90° in August.

Air and water temperatures are Key West's, but all areas are within 1° of each other by day. Key West's nights are 1–4° warmer than Key Largo's, and Marathon's January low is 56° against Key West's 65°. Winter water in the Atlantic runs the other way, with Key Largo about 3° warmer than Key West from January through March.

Peak rates Best value Shoulder Gulf water temperature
MonthMedian nightlyDifference from annualHigh / low air tempAvg. gulf tempWhat’s going on
January$366+5%75° / 65°71°Key West Half Marathon; Baygrass Bluegrass in Islamorada
February$375+7%76° / 66°71°Gigantic Nautical Market in Islamorada; Florida Keys Seafood Festival
March$375+7%79° / 69°73°Key West Orchid Festival; Marathon Seafood Festival
April$357+2%82° / 72°78°Seven Mile Bridge Run; Conch Republic Independence Celebration
May$3500%85° / 76°81°KEYS100 ultramarathon; stone crab season closes
June$3500%88° / 79°83°Key West Pride; Coralpalooza coral-planting dive
July$363+4%89° / 80°85°The two-day sport lobster season; Hemingway Days
August$3500%90° / 79°87°Key West Lobsterfest, as the regular season opens
September$310-11%88° / 79°85°Swim for Alligator Lighthouse; hawk migration counted at Curry Hammock
October$316-10%85° / 76°83°Fantasy Fest and its Zombie Bike Ride; stone crab season opens
November$327-7%81° / 72°78°Race World Offshore world championship in Key West
December$357+2%77° / 67°75°Key West Lighted Boat Parade; Key West's New Year's Eve drops

Based on the median Florida Keys nightly rate on FloridaRentals.com.


Planning a Florida Keys trip

Which airport depends on where you are going.

Miami is the shorter drive as far south as Tavernier, about 60 miles to Key Largo. From Layton down, Key West is closer, though it is a much smaller airport. Islamorada sits at the crossover, near enough the same either way.

Oceanside and bayside are directions, not amenities.

They tell you which side of the Overseas Highway a place sits on, the Atlantic or Florida Bay. A listing called beachfront may be a canal house with a dock at the seawall, so pay attention to the location on the map and ask the owner if you’re unsure.

Two roads in, one road after that.

US-1 comes down from Florida City on the 18-Mile Stretch, and Card Sound Road is the tolled alternative beside it. They meet in Key Largo, and everything south of there is US-1 alone, so a closure has no detour. The toll is electronic or billed by mail, never cash.

Much of the chain has a legal minimum stay.

Among the towns that set one, seven nights is the shortest. Key West works on licenses instead, so a licensed place there can rent for a night. Check the minimum on the listing and confirm it with the owner.


Florida Keys vacation rental FAQs

How much does a Florida Keys vacation rental cost?

+
The median Keys rental is $439 a night, which comes to about $2,975 for a week and $11,130 for a month. Tax adds 12.5% on any stay of six months or less, which is the county's own figure for what an overnight visitor pays. There is no booking fee on top of it, because you pay the owner rather than us.

What is the cheapest month to visit the Florida Keys?

+
September is the lowest at about $310 a night. Rates and demand both ease through the summer and into the fall. That stretch is Atlantic hurricane season, which runs June 1 to November 30 and peaks around September 10.

Which Key should I stay on?

+
Key Largo is the diving end and the quickest to reach from the mainland, while Islamorada next door is where the sport-fishing fleet ties up. Marathon splits the difference and puts both ends within an hour. The Lower Keys are docks, boats, and quiet nights. Key West is the walkable Key with more nightlife and culture.

Do you need a car in the Florida Keys?

+
Yes, a car is recommended to conveniently explore Florida Keys, though you can walk and bike in Key West. However, there is public transit across the Keys. Miami-Dade route 301 runs from Florida City into the Keys seven days a week and labels its stops by mile marker. The Lower Keys Shuttle carries on from Marathon to Key West with the transfer at MM 50. Some 301 runs stop short of Marathon, and the schedule ends up deciding your day.

Are the Florida Keys dog friendly?

+
There are plenty of dog-friendly vacation rentals with yards in the Florida Keys. Whether you can bring your dog out and about depends on the area. Florida's state parks don't allow pets. Monroe County's parks allow leashed dogs, and Marathon is pet-friendly on Sombrero Beach and Coco Plum Beach. Islamorada allows leashed dogs on Anne's Beach.

Are there real beaches in the Florida Keys?

+
There are a few, but they are not as prevalent as other areas in Florida. Bahia Honda State Park has three: Loggerhead and Sandspur on the Atlantic and Calusa on Florida Bay. Marathon has Sombrero Beach. Key West has Smathers, where the sand is free and the parking is metered. Fort Zachary Taylor is a state park and charges per vehicle. Everywhere else, waterfront means a canal, a channel or a dock.

Can I rent monthly or for a season in the Florida Keys?

+
Yes, and there are minimum-stay requirements in many areas of the Keys. Both Islamorada and Key West have strong monthly rental options. And if you stay longer than six months you are exempt from the county's 5% lodging tax.

What if I need to cancel my trip?

+
Because you book with the owner rather than with us, the cancellation policy is theirs, and it may vary from one listing to the next. Understand the policy before you book, and contact the owner directly with any questions.

All Florida Keys towns

Big Coppitt Key 1 · from $283
Big Pine Key 30 · from $131
Big Torch Key 1 · from $833
Cudjoe Key 24 · from $168
Duck Key 2 · from $157
Islamorada 113 · from $93
Key Colony Beach 34 · from $143
Key Largo 55 · from $85
Key West 71 · from $133
Little Torch Key 20 · from $150
Long Key 2 · from $164
Lower Matecumbe Key 1 · from $376
Marathon 128 · from $148
Plantation Key 2 · from $400
Ramrod Key 10 · from $122
Sugarloaf Key 6 · from $279
Summerland Key 42 · from $164
Tavernier 30 · from $180

Explore other Florida regions

Own a place in the Florida Keys?

Learn how you can list your property free for 60 days.

Contact us today