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Florida Keys Vacation Rentals

(570 rentals)
New
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

** IMPORTANT NOTICE **Building 1 Elevator Replacement Notice Schedule: September 9 – October 14The elevator in Building 1 will be temporarily out of service during this time due to a full replacement project. Please note that pricing has been adjusted to reflect this inconvenience.Located...

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$242
avg per night
Key Colony Beach House
Sleeps 14, 5 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 1 miles to Cabana Club

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Lovely full duplex that sleeps 14! Upstairs there are 3 bedrooms, 2 and a half bath’s with a wide open concept. The half bath is off the living room area. Four flat screen TV’s, hi speed wireless internet, gas grill and a lovely pool (heat is $200/wk optional). Pool is 10 X 20 and 4′...

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Featured review

"Lowe’s stay at 350 E4th Key Colony"

The location is great! The home, yard, and pool are beautiful. We would recommend the place to others.Some minor issues that should be addressed: the outside fish / bait cooler was very dirty and unusable...

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$661
avg per night
Cudjoe Key House
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

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

About this property

House - 2 Bedrooms, 2 Bathrooms, Sleeps 4. Come enjoy our hidden retreat in upscale Cudjoe Gardens. This home is conveniently located only blocks away from Cudjoe Gardens Marina. This single level home is situated on a crystal clear flow through deep water canal. The home features an in ground private...

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Featured review

"Perfect Keys Home"

We absolutely loved this home! We've been traveling to the Keys for 15 years and this is one of our favorites. A quiet neighborhood which is fantastic. Fred is excellent with communication.

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$217
avg per night
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

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

About this property

***SUMMER SPECIAL*** August-November $500 off regular price! Don't wait, books fast. Popular Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons ( **MONTHLY RENTALS ONLY!!) Come and enjoy our Paradise Found 2nd home. FREE BOAT DOCKAGE (with proof of insurance) In the fishing capital of...

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Featured review

"A slice of heaven!"

I had the pleasure of staying for the month of December. I've been staying in the keys during the month of December for the past 5 years and this is by far my favorite place! The condo was warm and inviting,...

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$185
avg per night
Marathon Cottage
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

4 Bikes 2 Kayaks Hot Tub Covered Outdoor Space 37 Ft of Dockage Fresh Interior Well-Equipped Kitchen Quick Walk to Sombrero Beach Lots of ParkingCozy and comfortable Sombrero Beach cottage! This light and airy single family home offers an open concept living, kitchen and dining area with large...

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$228
avg per night

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Islamorada House
Sleeps 2, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 5 miles to Founders Park

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Half Duplex HomeAre you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and manatees...

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Featured review

"Perfect spot."

My wife and I stayed at this 1 bedroom 1bath duplex on the water. It was perfect for the 2 of us. Clean. Owner was very attentive.

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$87
avg per night
Summerland Key House
Sleeps 8, 3 bedrooms, 3 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Keys Life Come on down to “Keys Life” and enjoy a great Florida Keys vacation. Located in one of the best deep-water boating areas. The crystal blue canals and superb deep-water boating will make your fishing days a dream. Great outside entertaining areas with a perfect pool to splash around...

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Featured review

"Keys life"

Enjoyed our stay at Keys Life. The home was beautiful. The weather was quite windy so we weren’t able to get out as much as we wanted in our boat but we were able to get some nice lobster! It was nice...

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$251
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Stay right on Bonefish Bay in this spacious 4BR / 3BA waterfront home with two master suites. Bring your boat and enjoy a 70-ft dock (40 ft available for use) with quick ocean access just 1 mile away. Relax in the private heated pool, fish from the dock, and enjoy peaceful waterfront views. Perfect for...

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Featured review

"Ma920"

Great place!! Loved it . Parking is tight, They do have trailer storage offsite. Jessica was easy to work with and highly recommend contacting her!!!

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$399
avg per night
Marathon Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Forget your worries in this spacious and serene space. Enjoy all that Marathon has to offer in this perfect location within walking distance to Cocoplum beach. This spacious completely renovated 2 bedroom condo offers everything that you will need for your vacation rental. Offering a boat slip right outside...

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Featured review

"Water’s Edge"

Fantastic condo in Marathon. Great location with its own community boat ramp, a dock right next to the condo, a pool, and a nice sandy beach a very short walk away. The best part was Katie Carillo the realtor...

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$178
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This estate has it all waterfront, large sun-filled pool and seawall dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and entertain your guests. The home was recently rented...

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Featured review

"Historic Downtown Vacation Stay"

Perfect spot to vacation!! Family friendly. This adorable house is downtown and close to everything!! I loved the yard and the porch was a favorite. Can't wait to return!

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$403
avg per night
Key Colony Beach House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

No detail spared in this completely renovated, top of the line stilted half duplex on 9th Street in highly sought after Key Colony Beach. Excellent end of the canal location makes for instant access to Vaca Cut! Head to the open waters of the Gulf or Atlantic! Open concept living and kitchen area overlooking...

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$293
avg per night
Big Pine Key House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Rentals by owner
  • WiFi

About this property

About the House • 3 bedrooms · 3 bathrooms · 3 beds · Sleeps up to 6 guests • Fully stocked kitchen with stainless steel appliances • Brand-new sheets and duvets for a luxurious sleep • In-unit washer and dryer for your convenience • Ceiling fan &...

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Summerland Key House
Sleeps 14, 6 bedrooms, 4 bathrooms
1 review

Key Amenities

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

About this property

Beautiful Ocean Front Home with six bedroom/Four bath. New memory foam mattresses in King and Queen rooms. Enjoy the heated pool, dock and beach. Located on Cudjoe Bay with panoramic view of the Atlantic and deep water swimming. Kayaks are provided for your enjoyment. There is a huge screened in porch...

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Featured review

"We would do it again!"

We enjoyed a family vacation for one week at this "villa". The view was spectacular and the interior spacious. There were plenty of spaces for all of us to sit and visit with each other. The pool was fun...

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$658
avg per night
Islamorada Condo
Sleeps 12, 5 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Sandglass 4 74980 Overseas Highway #4, Islamorada, FLLOCATION: Bayside Town House Located in Lower MatecumbeMINIMUM STAY: 7 DaysMILE MARKER: 74.9DETAILS: ONE OF A KIND!!! Magnificent two story townhouse with 5 bedrooms and 3 baths located on Lower Matecumbe in Islamorada....

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Featured review

"Family in keys"

Place was super - location decor and views- only issues we had were the a/c did not work well 1st 3 days and we couldn’t sleep in bedrooms even with fans- so the 3 nights we had to sleep in living area...

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$507
avg per night
Key Largo House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Bay Therapy 778 Bostwick Dr., Key Largo, FloridaLOCATION: Bayside canal home located in Key Largo MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 103DETAILS: Owners call this their special getaway "Bay Therapy" for...

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$266
avg per night
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

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.Located...

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Featured review

"Perfect vacation"

We enjoyed staying at this property. The owners communicated quickly and provided good information and recommendations. The condo is clean and the perfect amount of space for our family. The location was...

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$250
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 2 bathrooms
20 reviews

Distance to beach: 2 miles to Sombrero Beach

Key Amenities

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

About this property

A beautiful waterfront half duplex home in a tropical setting with views of the Gulf of Mexico and incredible sunsets. Recently renovated octagonal shaped home with wide open water views from every window. Newly furnished comfortable interior with all the amenities you'd expect. Brick pavers surround...

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Featured review

"Tropical oasis"

We have rented Brian A for the last 3 Januarys to escape the cold north. The location is wonderful because we like the 4 mile walk around the airport. We enjoy the heated pool and the occasional manatee...

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$314
avg per night
Summerland Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beau Soleil is located in the most sought after neighborhood in the Lower Florida Keys, Summerland Cove, on Summerland Key. A gorgeous gem, tucked away in privacy with tropical plants and fruit trees everywhere you turn!This home is situated on a great boating canal with plenty of dockspace for your...

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$323
avg per night
Tavernier House
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

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

About this property

The Atlantic Ocean greets you in this charming 1 bedroom condo on the top floor of building two, located in Ocean Pointe Suites Key Largo. Ideal for Friends, Couples, Solo & Budget Travelers, Key West Road Trippers, Snowbirds, Sea-foodies, Divers, Snorkelers & Anglers. Within a 10 minutes drive...

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$236
avg per night
Sugarloaf Key House
Sleeps 10, 5 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Sea Magic on Marlin – Panoramic Open Water Views & Spacious5-bedroom HouseYour Sugarloaf Key adventure begins at this beautifully located waterfront home. Panoramic water views and access allows for boating, swimming, kayaking, snorkeling, and fishing and this 5-bedroom house welcomes...

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$429
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms
2 reviews

Distance to beach: 8 miles to Founders Park Beach

Key Amenities

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

About this property

An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located near the heart of Key Largo and has the distinction of being Key Largos newest oceanfront gated destination, with some of the most unique amenities in all...

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Featured review

"Gorgeous view, beautiful home"

From the moment we opened the door, the view was absolutely captivating - better than the photos!The condo is beautifully appointed with a cool beachy vibe and everything you'd need to make your stay...

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$418
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 3 bathrooms

Distance to beach: 0.5 miles to White Marlin Beach

Key Amenities

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

About this property

*******Check us out on VRBO No. 2003434******** Please go to ....**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.As soon as you walk into this home you will...

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$350
avg per night
Key Largo Estate
Sleeps 20, 7 bedrooms, 5.5 bathrooms
3 reviews

Key Amenities

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

About this property

Large, very spacious, beautifully appointed 7 BR home with breathtaking ocean views, large dock, pool, 2 jacuzzis, BBQ grill, 4 kayaks, large tiki, two fully equipped kitchens, all new appliances and major upgrades since Irma. Comfortably accommodates multiple families. Very private and secure with property...

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Featured review

"Perfect house for families!! Amazing outdoor space!!"

We loved our stay at Casa Lorelane! We had 18 people and never once felt crowded. The living area on the second floor was amazing. The second kitchen on main floor made it easy to prepare food to enjoy...

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$800
avg per night
Islamorada Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs...

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Featured review

"Unit 205 Beacon Reef"

Love Beacon Reef and the unit was very comfortable and well equipped. Very close to the pool and the staircase from the balcony was convenient

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$183
avg per night
Sugarloaf Key House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Amazing Waterfront Home with Fabulous Pool and Sunset ViewsWelcome to the Sugarloaf Guest House, the perfect Florida Keys Island Getaway. As you enter the gate to this charming seaside cottage, you will experience its charm and relaxing vibes. A gorgeous new pool with graceful waterfalls make it the...

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$395
avg per night
Sugarloaf Key House
Sleeps 10, 5 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

This pet-friendly home completed in 2012 has 5 rooms, 3 king-size beds, and 4 twins plus a twin sofa bed and three full bathrooms. The home has a huge kitchen with custom made wood cabinets and top of the line stainless steel appliances including an indoor gas grill and a standing freezer: to keep the...

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Featured review

"Take Your Vacay from 0 to 60 in 2.5 seconds"

SIX STARS * * * * * *This is a wonderful home with channel access right behind the house. It's perfect for the whole family, very spacious. The owners are very accommodating, making sure everything...

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$279
avg per night
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • 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. Seas the day – or just relax – you’re on island time!The Space This unit is located in building 3 which is a desirable building. Featuring...

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$248
avg per night
Islamorada House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Villa Riolo 130 Columbus Drive, Islamorada, FLLOCATION: Gated Oceanside House on canalMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 76.5DETAILS: "Villa Riolo" is an updated single family stilt home and perfect...

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$176
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Key Amenities

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

About this property

Immerse yourself in the luxury and beauty of Oceanside, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada. Our 4 bedroom home invites you to experience modern coastal comfort while its nearly 3000 square feet of indoor space provide ample room for family and friends....

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Featured review

"Beautiful stay"

We had the best time at this house! Giovanna and her husband were wonderful hosts and were on top of everything we needed. The house itself is in a great location close to shops and restaurants. Book the...

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$943
avg per night
Islamorada House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Fisherman's Gem 113 Iroquois Drive Islamorada, FloridaLOCATION: Oceanside Canal home with Boat dock and Boat RampMIMINUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 74This waterfront, ground-level Islamorada home, featuring...

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$160
avg per night
Marathon House
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

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

About this property

Welcome to DragonFly Lite our home in Marathon, FL in the heart of the beautiful Florida Keys, the house has 2 bedrooms a Queen in the master and 2 twins in the guest room, one bathroom + our outdoor shower, all the towels you will need for the pool or beach (please leave the sand outside). It’s...

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Featured review

"A Magical Place to Isolate"

Though Dragonfly Lite would be a marvelous place to vacation anytime, it proved especially so in a global pandemic. We had everything we needed right there on property. The pool is pristine, the home was...

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$648
avg per night
Key Largo Mobile home
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Escape to Key Largo and experience the ultimate Florida Keys getaway! Whether you're looking for a family vacation, a trip with friends, or a peaceful retreat, this newly remodeled 4-bedroom, 3-bathroom home offers the perfect setting to relax, explore, and make lasting memories.Key Features:Spacious...

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Featured review

"Spacious home"

We stayed in this home for a month and we had a wonderful time. The home is very spacious with 4 bedrooms and 3 bathrooms. It is remodeled and it has 2 family rooms. It had space for my boat and parking...

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$200
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
20 reviews

Distance to beach: 0.1 miles to At Kawama Yacht Club

Key Amenities

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

About this property

Enjoy Key Largo - A Year Round Vacation Paradise *** Short Term Rentals Available**** * * NO PETS * * *NO PETS * * *NO PETS * * *. - the Associate does not permit renter's pets!!!* * * SPECIALS LISTED HERE WHEN AVAILABLE * * *RATES are based on Dates, Length of Stay and Number of...

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Featured review

"Nice place"

They are individually owned condos with different layouts. Ours was nice but don’t expect it to be a five star hotel, they’re family vacation homes. There are three pools and a playground. It has a...

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$151
avg per night
Summerland Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Serenity found in the Florida Keys! This home is situated on a beautiful canal in the Jolly Roger Estates of Little Torch Key. There is plenty of room for your boat with access to the best boating, fishing, diving, and snorkeling in the lower Keys.The exterior of this home boasts a large concrete...

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$188
avg per night
Islamorada House
Sleeps 4, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Marlin House 156 Venetian Drive, Islamorada, FL 33036LOCATION: Bayside Canal home located in the popular Islamorada neighborhood of White Marlin BeachMINIMUM STAY: 90 days, this is a 3 month minimumMILE MARKER: 74.5DETAILS: You will love this charming and cozy Keys Holiday...

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$204
avg per night
Tavernier Mobile home
Sleeps 4, 2 bedrooms, 2 bathrooms
9 reviews

Key Amenities

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

About this property

This property is located on a very unique spot. Very private. Too perfect to describe.During the day you could sunbathe while fishing for snappers, tarpon and lobsters from your private dock. Later on you may want to jump in for a swim or cruise the area on the kayak At early evening you may enjoy...

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Featured review

"Paradise!"

This is an amazing rental and the owners are the nicest people you will ever meet. The home is on the water and one house from the Gulf of Mexico. Sit on your own private dock and watch the Manatees, Dolphins,...

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$180
avg per night
Islamorada House
Sleeps 3, 1 bedroom, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Sunshine Place 84371 Overseas Highway, Islamorada, FLLOCATION: Oceanside HouseMINIMUM STAY: WeeklyMILE MARKER: 84.3DETAILS: "Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing...

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$255
avg per night
Key Largo House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Island Tropical Bungalow! This lovingly maintained, delightful and spacious 3/2 with large expanded porch and Boat ramp just crossing the street makes a great getaway. All utilities are included (water, power, wifi, tv) Large shed in back with laundry (washingmachine and dryer). Totally redone...

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$286
avg per night
New
Key West House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Old Town cottage!! Great location! 2 bedrooms 2 full bathrooms, Both bedrooms have King beds and french doors to outdoor sitting areas. Great front porch to watch the conch tour train go by.

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$333
avg per night
Key West House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Very good location in Big Pine, deer paradise, a very quiet place to relax and rest if what you want is incredible peace to relax, believe me, this is your place, lots of outdoor space, the house is on a corner, very cozy inside and out, outdoor hammocks, many places to sit and spend a lovely afternoon...

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$183
avg per night
Summerland Key House
Sleeps 10, 4 bedrooms, 5 bathrooms

Key Amenities

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

About this property

This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atlantic. Sea Wall has room for (1) 24' boat. This home can sleep 7 adults and 2 small children. There are 4 bedrooms and 4-1/2 bath. Fully stocked modern kitchen, great out door space...

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$428
avg per night
Big Pine Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

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

About this property

This lovely waterfront home has it all. This fantastic community is one of the most unique places in the world. In minutes you can explore the beautiful back country or Ocean by kayak or boat. Marine Life sightings and fishing is the best in this area. You can lay back and relax, away from it all and...

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Featured review

"Peace"

House was perfect for me--quiet and peaceful. Never rented a house with a pool before, but this was wonderful. No mosquitos. Boat dockage was ideal. The fish cleaning table, which I used a lot, needs a...

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$145
avg per night
Big Pine Key House
Sleeps 8, 4 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 3 miles to Bahia Honda Park

Key Amenities

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

About this property

Modern 4 bedroom 2 bath stilt home centrally located in Big Pine. Heated salt water swimming pool. Corner canal front lot with 120 ft of dockage. 5 min. to the Gulf and 10 min. to the Atlantic. Close to the Winn Dixie grocery store. Free public boat ramp 5 min away. Room on property to park 6+ cars...

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Featured review

"Croton house"

Well, we think the house is very nice and clean. Great location, lovely neighbors nice quiet place we have only positive things to say and nothing negative so have a great day

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$200
avg per night
Key Colony Beach House
Sleeps 14, 6 bedrooms, 5 bathrooms

Distance to beach: 0.3 miles to Sunset Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautiful, modern and stylish home is perfect for families and group vacations and boast 2 full kitchens.It features high quality and modern furniture and beds, a fully equipped kitchens, high-speed wireless internet and a private, heated pool.The Upper side has 3 bedrooms and 2 bathrooms,...

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$930
avg per night
Key West Condo
Sleeps 8, 3 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Mar Y Sol – Luxury Oceanfront Condo in Key West Breathtaking Views. Unbeatable Comfort. Perfect Location.Welcome to Mar Y Sol, a stunning oceanfront condominium located at 1800 Atlantic, Key West. This beautifully renovated 3-bedroom, 2.5-bathroom vacation rental offers sweeping views of the...

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$536
avg per night
Marathon House
Sleeps 5, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

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

About this property

Our wonderful, Oceanside and waterfront home is just two minutes from the Atlantic Ocean and Vaca Cut. No bridges to the Atlantic and super easy to access the Gulf via Vaca Cut.This home is completely remodeled and features brand new furniture throughout. The 55 foot dock is brand new and awaits your...

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Featured review

"Peaceful palms winter retreat"

We had a great time escaping the cold weather up north. Accommodations were excellent as were our hosts Jamie and Charlie, they were very responsive to any questions we had and made us feel welcome. We...

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$250
avg per night
Summerland Key Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best deep water boating in the Lower Keys!Decorated in fine island-style this private home is definitely a 5-star property. Tile floors, open and airy kitchen, living and dining area...

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Featured review

"Nice home, greatl canal good to work !"

Not my first time with action keys, always had good result with everyone at this company! Wish they would rework there utilities policy , it’s hard enough to pay rent for a month.

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$195
avg per night
Summerland Key House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Margarita Manor – Your Tropical Escape in the Florida Keys!Set your watch to island time and relax at Margarita Manor, a vibrant waterfront oasis perfectly suited for sun-chasers and boating enthusiasts alike. Located just moments from open Atlantic waters, this breezy retreat offers...

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$253
avg per night
Key Largo House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Spacious 3-story home with private pool, jacuzzi, terraces, and bright open living spaces.Perfect for long stays, with a full kitchen, fast WiFi, multiple lounge areas, and a quiet backyard. Great location in Key Largo -minutes from Pennekamp Park, nature trails, beaches, marinas and great local restaurants.Ideal...

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$245
avg per night
Key Colony Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

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

About this property

Come vacation at our 2 Bedroom, 2 Bathroom, canal front property located on the Island of Key Colony Beach in the Middle Keys. Our house sleeps 4 people including kids and has dockage right our back for up to a 40-foot boat. You can fish right off our dock on the Island's largest, deepest, most private...

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Featured review

"Perfect Vacation Getaway!"

We had a wonderful stay and highly recommend this vacation rental! The property was very clean, and the kitchen was well equipped with everything we needed. We especially enjoyed fishing from the dock and...

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$165
avg per night
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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.