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Florida Keys Vacation Rentals

(574 rentals)
Key Largo House
Sleeps 6, 3 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 40 feet to Across the street

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

FAMILY FRIENDLY GORGEOUS HOME WITH DIRECT WATER VIEW OF LARGO SOUND! WATCH THE SUN RISE FROM THE COMFORT OF YOUR LIVING ROOM! 3 BEDROOMS 2 BATHROOMS BEACH AND BOAT LAUNCH INCLUDED IN RATE! THIS IS THE OPPORTUNITY OF A LIFETIME! KING SIZE BED IN MASTER BEDROOM, Queen bed in 2ND BEDROOM AND TWIN...

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Featured review

"The perfect getaway spot"

This place is amazing, beautiful beach right out the front door is why we come here. The host is the best, Nancy catered to all our needs. The home is nicely decorated, it had everything we needed. We will...

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$200
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Anne's Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

House, 3 Bedrooms, 2 Baths, (Sleeps 4-6)Spacious ground level home that will be easy on your legs--NO stairs to climb! The home is fully equipped with linens for the king, queen, and 2 double beds. The master bedroom has its own bath. A separate media room with a flat screen TV as well as a large...

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$330
avg per night
Marathon Condo
Sleeps 4, 1 bedroom, 1.5 bathrooms
4 reviews

Key Amenities

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

About this property

Newly Built,1 Bedroom 1 Bathroom unit, Marina, Largest Olympic Pool in the Keys overlooks the Atlantic Ocean, Fun and Sun. Great amenities, close to everything.Outdoor bar b q grills, great Sunsets from the Pool, Tikis and Docks.

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Featured review

"Great stay"

Thank you so much for an amazing stay. We couldn’t have asked for a better rental. The rental had so many amenities that other places have not. Will definitely stay here again.

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$199
avg per night
Islamorada House
Sleeps 10, 3 bedrooms, 3 bathrooms
5 reviews

Distance to beach: 0.3 miles to Anne's Beach

Key Amenities

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

About this property

Enjoy this modern and recently updated lagoon front 3 bed/3 bath single-family home on the Gulf side of Islamorada at MM 73.5, minutes from the Channel 2 and Channel 5 Bridges, offering immediate access to the oceanside of Lower Matecumbe Key. Dockage is available for up to a 35' boat, or use the...

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Featured review

"On a scale of 1-10 this property is a 12 overall !"

We have rented this property for 3 years and have been extremely pleased with all aspects from great hosts, nicely appointed house, heated pool, canal/dock access , easy out to ocean or bay, plenty of...

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$343
avg per night
Key West Townhome
Sleeps 7, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Relax with family and friends in your own tropical paradise at this spacious townhome in Key West's beautifully landscaped & maintained Golf Club. Located in a private gated community with resort style amenities, it is just minutes away from the beaches, world class restaurants, water sports...

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Featured review

"our vacation at Key West Golf Club"

We had wonderful time enjoying the beautiful weather and the beauty of all the attractions at Key West. Our condo was all we needed to fulfill our stay. It was clean and we enjoyed being right on the golf...

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$203
avg per night

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Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 100 yards to Port Antigua Private Beach

Key Amenities

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

About this property

This spectacular 3/Bed 2/Bath canal front home is located in Lower Matecumbe Key, a part of Islamorada island. Enjoy the exclusive neighborhood of Port Antigua—just a 5 minute walk to our private beach.The house is nautically designed, with a spacious and open floor plan. There's a large...

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$277
avg per night
Key Largo House
Sleeps 6, 3 bedrooms, 2 bathrooms
11 reviews

Key Amenities

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

About this property

Play all day in Key Largo! If you like fishing, snorkeling, diving, kayaking, paddle boarding, wakeboarding, and nature, you can do it all here at Easy Livin’! Bayfront home on open water with dock and small private ramp. Love fishing? House is close to Flats, Backcountry, Reefs and Offshore. Dock...

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Featured review

"A special place!"

This is our 5th year spending a winter month in Key Largo... our first at Easy Livin. We are very pleased to have found it. It's tucked away from the route 1 traffic, but easy access to everything we need/want....

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$349
avg per night
Key West Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Just a few houses off Duval, this wonderful retreat occupies the ground level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. A large covered front porch welcomes you to sit and watch the Key West world go by, imagining what life was like in the early days of...

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$234
avg per night
Key Largo Estate
Sleeps 16, 6 bedrooms, 6 bathrooms

Distance to beach: 6 miles to Pennekamp

Key Amenities

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

About this property

Recently renovated large 6 bedroom, 7 bathroom Ocean Front House on 5 Acres. Gated from the main road. It can comfortably sleep up to 16 people. Covered parking for up to 6 vehicles and outside parking for several more. This estate is surrounded on 3 sides by park lands and the Atlantic ocean. If...

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$793
avg per night
Islamorada House
Sleeps 10, 5 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Paradise Palms!Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-bath home serves as an excellent setting for your tropical getaway. Ideally located in Islamorada on Lower Matecumbe Key, you will have convenient access...

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$557
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...

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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...

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$243
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...

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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.

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$191
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...

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$1,990
avg per night
Key Largo Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms
9 reviews

Distance to beach: 100 feet to On Site

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This recently remodeled and upgraded, this 2 bedroom, 2 bathroom, Ocean Front Condo has spectacular Ocean, Marina, Beach & Park views from the Living Room, Dining Room, Kitchen, Master Bedroom, Balcony and even the master bathroom.THIS CONDO IS CLEANED & SANITIZED TO THE NEW CDC STANDARDS.Included...

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Featured review

"Amazing!"

This condo was perfect for our family of 4. We have two 21 year old daughters, we came to celebrate their birthday. The condo was spacious and had plenty of room for all of us. The kitchen was well stocked...

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$262
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...

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$248
avg per night
Islamorada Townhome
Sleeps 6, 2 bedrooms, 2.5 bathrooms
2 reviews

Key Amenities

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

About this property

Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse located...

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Featured review

"Lazy Daz Beac House"

Excellent couple to work with. Great communication. The rental was beautiful and clean. We had a problem with the rental and they communicated with us and together we solved the problem. They went over...

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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...

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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!

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$247
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms
5 reviews

Key Amenities

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

About this property

5 Star Modern New Construction Bayfront Home With Private Dock and PoolIsland Dreamz Bay House is a piece of paradise on the Vaca Cut waterway in Marathon. Gorgeous and brand new 5 bedroom, designer decorated, 4 bath single-family home with 36 ft. of assigned dockage. Private pool can be heated upon...

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Featured review

"Island Dreamz a stunning home, lovely view and perfect location in the Keys!"

This was our second stay at Vaca Cut at The Tides. We loved this gorgeous home with its exquisite design and comfort. The house was immaculate ~ kudos to the pros who keep this home clean and well stocked...

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$820
avg per night
Ramrod Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Come enjoy this newly listed property on Beautiful Ramord Key house with a southern view of Newfound Harbor and the Atlantic !! House has a 60 ft+ dock for your water toys. Enjoy lobster season, fishing (back water and deep sea great snorkeling and dining all minutes away. Ramrod is easy boating...

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$267
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...

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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

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$300
avg per night
Key Largo Townhome
Sleeps 6, 2 bedrooms, 2 bathrooms
7 reviews

Distance to beach: 100 feet to 4 on site

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This is a 2 story, 2 bedroom, 2 bathroom townhouse that comfortably sleeps 6 in a 24 acre Resort / Condo complex.WE FOLLOW THE CDC GUIDELINES FOR CLEANING AND SANITIZING THIS PROPERTY.Included in the price are Taxes, Cleaning, WiFi, a Golf Cart, Kayaks, Paddle Boards, Bikes, Fishing Gear, Snorkeling...

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Featured review

"very nice complex"

Great condo 3 pools, lots of grounds to walk. Loved the view , 4th floor. Would rent again.. was close to stores and restaurants.

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$280
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,...

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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...

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Islamorada Apartment
Sleeps 2, 1 bedroom, 1 bathroom
5 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

The apartment is in a house on the canal and across from the beach with beach access. It is situated on the ground floor of a two storey Keys house where you would be the only residents. All the amenities would be yours and you would have space, tranquility and privacy in the tropically planted landscape....

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Featured review

"Perfect rental for one couple"

This is the perfect apartment for one couple. Wonderful location on the oceanside with ocean views across the street. Has a great dock for your boat with great ocean access. Fish cleaning table is under...

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$150
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...

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$233
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....

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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...

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$240
avg per night
Special Offer
Marathon Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 bedrooms, 2 bathrooms ideal getaway in Coco Plum Beach, the Florida Keys. Great value and our reviews are excellent! Small Pets OK for downstairs unit.We have two units in the same building.Amazing amenities, that include waterfront swimming pool, boat dockage included for boat up to 40’,...

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Featured review

"Welcome to Paradise"

Location, Location, Location!This place was perfect for remote work or a relaxing vacation, with the boat docked just steps from the door. It truly offers the best of both worlds!Graceful manatees...

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$183
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...

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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...

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$1,165
avg per night
New
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,...

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$1,052
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...

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$199
avg per night
Islamorada House
Sleeps 10, 4 bedrooms, 2 bathrooms
3 reviews

Key Amenities

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

About this property

4 Bedroom 2 bath home with private dock and private pool with direct open access to the ocean and convenient access to the bayside through Tavernier Creek. This is both family-friendly and a fisherman's dream. Our home sleeps 8 with every comfort you would want while on vacation in the keys...Large...

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Featured review

"It's like coming home!"

This is our third year at Blue Dorado. We love it here! Everything was perfect for our family. The access to the Ocean and Tavernier Creek is amazing. We saw so many beautiful sunrises and sunsets.

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$283
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...

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Featured review

"Keys Condo"

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

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$302
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,...

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$242
avg per night
New
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...

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$350
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,...

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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...

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$302
avg per night
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Relax & Recharge at our Quiescent Condo with Stunning Views of the Blue Green Colors of the Atlantic all Nestled on 60 Secluded Acres. Situated in Tavernier, the property is centrally located between Key Largo and Islamorada, with restaurants, shops, attractions, charter & dive boats and more...

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$275
avg per night
Key West House
Sleeps 10, 4 bedrooms, 3 bathrooms
4 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...

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Featured review

"Beautifully Appointed Historic Home in Old Town"

I really can't rave enough about this home and the hospitality of the owners. The house is a beautiful historic home in old town that has been lovingly restored. The outdoor living space and the open to...

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$531
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 in the quiet beauty of 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...

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$200
avg per night
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,...

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$400
avg per night
Islamorada House
Sleeps 10, 3 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Newly renovated 3/2 Canal front home with brand new pool, deck and front gates for privacy!The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms,...

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Featured review

"We love this house!"

2022 was our 2nd time renting this wonderful home. The location is fantastic, and the house and property offer everything you can imagine. Outside is a paradise with a refreshing pool (with fun lights...

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$500
avg per night
Key Largo House
Sleeps 7, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Welcome to Villa Azzurra!This beautifully decorated, island style beach home can comfortably accommodate seven guests, and boast three en suite bedrooms, a fully stocked gourmet kitchen, private pool, endless water views, and a bayfront beach.The first floor offers a high quality kitchen...

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Featured review

"Perfect Florida Keys Vacation Home"

We loved Harbor Hideaway for our month long getaway to Islamorada. The home is beautiful with gorgeous sunset views and huge private balconies. The newly renovated bathrooms are fantastic! The outdoor...

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$280
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Come have your first sunset drinks compliments on us at Island Fish Company. $100 Gift Certificate to Island Fish Company Included. No Expense Spared! New Construction Bayfront Home With Private Dock and Pool.5 O'Clock Somewhere Bay House is a piece of paradise on the Vaca Cut waterway in Marathon....

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Featured review

"Fabulous vacation rental for our family celebration with all the amenities and comforts of home plus a fabulous view!"

This vacation getaway home had everything we needed plus Lauri was an extremely responsive host. The location was excellent. We could walk to the Aquarium that was across the canal or drive ten minutes...

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$720
avg per night
Key Largo Townhome
Sleeps 8, 3 bedrooms, 3 bathrooms
9 reviews

Distance to beach: 100 feet to 4 on site

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This 3 story, 3 bedroom + den, 3 bathroom, 4 balcony waterfront (Salt water Lagoon with tropical fish that you may hand feed) townhouse in Key Largo can comfortably sleep 8 people.This property is cleaned and sanitized to the current CDC standards.Included at no extra charge are free WiFi internet,...

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Featured review

"Awesome Community and Rental"

I rented from Norman Wortman and he was absolutely outstanding.Kawama is a wonderful community that really replicates "Old Florida." The rental had a wonderful view of the lagoon. Lots of space and...

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$294
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...

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$513
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...

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$417
avg per night
Ramrod Key House
Sleeps 8, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

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

About this property

Beautiful , home on deep water canal in desirable Breezeswept Estates is your private resort for a minimum of 28 days . Heated, saltwater pool adjoins huge ground level great-room with living area, dining area, shower , gas grill, pingpong table and so much more contained in private setting ! 40 ft dock...

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Featured review

"Desiderata"

Very nice pool & dock area. Neighbors very friendly. Downstairs area very nice for socializing near pool area. House was comfy for family with adults & children. A great location for restaurants...

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$302
avg per night
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

In the heart of Tavernier lies this beautiful 2-bedroom condo that combines the Florida Keys' breathtaking scenery and lively atmosphere. Nestled just a short 19-minute drive from the renowned John Pennekamp Coral Reef State Park, this property offers the perfect base for your tropical getaway.As...

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$250
avg per night
Tavernier House
Sleeps 12, 5 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Captain's Quarters! Located on Plantation Key (Mile Marker 90), this beautifully updated five bedroom and four bathroom canal-front home offers a resort-like experience.The main living area, located on the second floor, features three bedrooms and two full bathrooms. The open-concept...

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$459
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...

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$250
avg per night
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning

About this property

Within a 10 minute drive of Key Largo or Downtown Islamorada's best Restaurants, Bars, State Parks, Dive Boats & Fishing Charters.You'll enjoy this Charming 2 bedroom 2 bath suite with sleeper sofa in Ocean Pointe Suites; a private gated community nestled on the Atlantic's Edge....

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$237
avg per night
New
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...

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FAQ

Location & Specific Keys

What is the difference in atmosphere between the Upper, Middle, and Lower Keys?

The Upper Key has a relaxed vibe with a lot of nature preserves and parks to see. The Middle Keys have a laid-back vibe along with popular places to snorkel, dive, and swim. The Lower Keys, along with Key West, have an energetic vibe.

Which Key is best for nightlife and attractions versus quiet relaxation?

The Lower Keys have a vibrant nightlife, while the Middle Keys offer a relaxing atmosphere.

How do I choose the right Key to stay on for my vacation goals?

One of the simplest ways to choose a Key is to decide which attractions you want to see. Then, choose the Key that gives you the easiest access to those attractions.

Are there any lesser-known Keys that offer good rental options?

Sugarloaf Key, Little Torch Key, and Tavernier Key are lesser-known Keys with houses and other types of vacation rentals.

Activities & Lifestyle

Which Key is the best home base for fishing, diving, or snorkeling trips?

The Middle Key is your best bet for fishing, diving, and snorkeling fun, particularly off the coast of Marathon.

What are the "must-do" activities when staying in the Florida Keys?

Some “must-do” activities include snorkeling and swimming around the reefs, visiting the Hemingway Home and Museum, touring Marathon Marine Park, and visiting Dolphins Plus Bayside.

Are the rentals close to good restaurants, marinas, and public beaches?

Yes. Many Florida Keys vacation rentals are close to restaurants, marinas, and public beaches. Some properties are close to shopping areas, state parks, boat rentals, and breweries as well.

What is the best way to get around the Keys – is a car necessary?

Though there is public transportation like the Freebee Shuttle, renting a car is a great way to take in the sights around the Keys.

Booking & Logistics

What are the pros and cons of renting directly from an owner versus a property manager?

One pro of renting directly from an owner is flexibility. You may be able to negotiate on rent or fees with a property owner, whereas a property manager isn’t likely to negotiate. However, a property owner may not be as quick as a property manager to address rental issues, including maintenance.

What are the best websites for finding "For Rent By Owner" (FRBO) properties in the Keys?

Florida Rentals is one of the best websites to find FRBO properties.

How can I protect myself from scams when booking directly with an owner?

One way to protect yourself is to conduct an address search to ensure the property exists. Also, don’t pay the rent with a gift card, cash, check, or wire transfer. Be suspicious of a large property with lots of amenities and very low rent.

Do rentals by owner offer more flexibility on price or stay dates?

Yes. Rentals by owner offer more flexibility regarding price and stay dates. While a property management company has to answer to the owners, the owner of a rental can make changes at will.

Property Type & Communities

What types of houses are common for rent in the Keys (e.g., stilt homes, bungalows, canal-front homes)?

Canal-front homes, bungalows, and cottages are common rentals in the Florida Keys.

What is the benefit of renting a house on a canal versus one that is oceanfront?

A house with a canal gives you a place to boat and fish in still water right in front of the property. Renting an oceanfront home offers a great view of the ocean, but not a convenient place for fishing and boating.

Do most house rentals come with private boat dockage?

Yes, many house rentals in the Florida Keys include private docks.

Are there large houses available that can accommodate multiple families or big groups?

Yes, there are large houses in the Florida Keys suitable for big groups. Use the search filter to find a rental that can accommodate all of your guests.

Amenities & Features

What are the essential amenities for a Keys rental (e.g., boat slip, fish cleaning station, outdoor seating)?

Essential amenities for Florida Keys rentals include a patio or deck, boat slip, Wi-Fi, heated pool, and kitchen.

Is a private pool a common feature for house rentals in the Keys?

Yes, a private pool is a common sight in a description of house rentals in the Keys.

What should I look for in terms of parking, especially if I'm bringing a boat trailer?

Look at the property’s description to see if there is parking available. Some owners have parking areas for boat trailers. If you don’t see any information about trailer parking, message the property owner to get specifics.

Are kitchens in these homes typically well-equipped for cooking a fresh catch?

Yes. Along with a fish cleaning station, many rentals have a well-stocked kitchen with appliances for cooking seafood.