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Florida Keys Vacation Rentals

(574 rentals)
Key Largo Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms
7 reviews

Key Amenities

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

About this property

DIRECT BAYFRONT | Mile Marker 99 | Gated Community | Resort-Style Living | 28-Night MinimumMulti-million dollar, unobstructed bay views + the peace and privacy you come to the Keys for. Located at Mile Marker 99 in Key Largo, this direct bayfront condo delivers a true resort-style experience in a...

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Featured review

"Gorgeous Condo!"

Absolutely loved my time here! The condo has all updated bathrooms, kitchen and laundry! The master bathroom is beautiful and felt like I was in a hotel! Views are gorgeous and the location is great! Will...

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$250
avg per night
Key Colony Beach House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Lovely and spacious 3 bedroom, 2.5 bath half duplex on Key Colony Beach. Very spacious townhouse style on the shady side of 9th St. All tile floors downstairs, with an open concept, large well equipped kitchen with a nice size bar that seats 5, along with a separate dining table. There is an adjacent...

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Featured review

"Wonderful"

We have been staying in Key Colony for many vacations. Each time we have stayed in a different house, reason being that I usually wait too long to make reservations. This house definitely was by far the...

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$251
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 upper level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. The carefully restored Dade County Pine wood walls and Red Oak floors evoke a more relaxed era in the Southernmost City. The home opens...

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$228
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Mile marker 77. Deep Water ocean side canal with direct access to the Atlantic Ocean and a straight shot to Alligator Light House. Sunny Patio and splash Pool. 4 Bedrooms/4 Baths. Sleeps 8. There is no cable package with this home so please bring your passwords for live streaming from the smart TVs.The...

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$330
avg per night
Key West House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner

About this property

A phrase the locals use quite often here in Key West is that we are "Living the Dream" - if you come and spend some time here you will see why! Steps away from the Key West Seaport and just a few blocks from world famous Duval Street this property is located on Eaton Street in Old Town Key...

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$500
avg per night

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Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

NEW!!! FULL BACKYARD REMODEL!!! NOW OPEN FOR BOOKING!!! INGROUND POOL INSTALLED - HEATED! AND THE HOTTUB PRICES STILL REFLECT PRE RENOVATION PRICES HURRY IN BEFORE THEY GET RAISED! ***New backyard photos coming soon.***Welcome to your dream Serenity Oasis in the heart of the Florida Keys! This...

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Featured review

"Named correctly"

The name of this property, Serenity Oasis, is exactly how you feel when you are here. Stunning decorated house in a very quiet neighborhood. The pool is wonderful with several different levels of built-in...

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$404
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
Key Colony Beach House
Sleeps 8, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • WiFi

About this property

Manatee Love awaits you! Nicely updated, spacious 3 bedroom, 3.5 bathroom canal front home on beautiful Key Colony Beach. Enjoy over 1,650 square feet of open concept space, large living area overlooking the wide, deep canal, brand new kitchen and appliances, granite countertops, and a Keurig! Well-equipped...

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Featured review

"Sting Ray"

The property was clean. Kitchen had everything needed. Exceptional outdoor pool. Loved the 2nd floor screened in rear porch.

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$228
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • WiFi

About this property

Mile Marker 74 – Bayfront – Beachfront – Handicap Assessable – Dockage for 30′ boatThis amazing beachfront home is a must see! Located on one of the few white sand beaches in the Florida Keys, Gulfview is a private home located on Lower Matecumbe Key in Islamorada in...

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$433
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to Oceanview Oasis, a most spectacular open water home on Summerland Key. This is a completely remodeled, state of the art, waterfront retreat with new oceanside pool, adjacent spa and screened porches on two levels for outstanding views at every turn.Interior living space offers a split floor...

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$467
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Key Lime Sunrise Watch the sunrise & feel the tropical breezes while sipping your coffee from the comfort of the upstairs screened terrace of this lovely and neatly maintained two bedroom two & a half bath home situated on Sombrero Beach Road. This charming getaway is within walking/biking distance...

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Featured review

"We had a very nice visit."

171 10th St. The duplex was very neat. We loved the screened in back porch (had to keep the fans going because of the heat). The pool chairs lacked comfort but we had seen that in the pictures and brought...

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$299
avg per night
Key Colony Beach House
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

DescriptionAdorable two bedroom, two bathroom half duplex on stilts overlooking the extra wide, deep canal and the Par 3 Golf Course on the streetside. This home is tidy and spacious. It offers soaring ceilings, tons of natural light, lots of covered seating, a beautiful concrete pool, 37 feet of...

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$357
avg per night
Marathon Bungalow
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Start planning your perfect escape to the Florida Keys! Blue Ocean Bungalow is ideally located on a wide, deep-water canal with easy access to world-class fishing in the Atlantic and the Gulf. Enjoy all the amenities needed for a perfect island vacation: airy open living areas with canal views, cozy sunroom...

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Featured review

"Wonderful keys retreat!"

Thank you . We had a great time..we fished, snorkeled and spent a wonderful time with family and friends.. we all highly recommend!!

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$305
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This home is the ideal getaway for the whole family! The interior of the home is super spacious with an updated kitchen that looks out over the canal and large pool.There are three bedrooms, two bathrooms, and a large family area with a big screen television for your entertainment. Not to be outdone,...

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Featured review

"Outstanding location for fishing, boating, & diving!"

Stayed at this gem before and after Lobster mini season. The pool was perfectly refreshing after a day in the sun on the water. There are several free boat ramps nearby. Great proximity to the Looe key...

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$289
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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$203
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Summer never ends in the Florida Keys! Endless Summer is located on Summerland Key in the very desirable Summerland Cove neighborhood. This is a two bedroom, two bathroom comfortable home with additional and very accommodating living space on the lower level.Upstairs is open concept living with a...

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$183
avg per night
Summerland Key House
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Looking for the perfect getaway for your Florida Keys vacation? Look no further! Tropical Oasis is just the home for you and your guests with only 23 miles to Key West; not that you’ll ever want to leave the beautiful views of the mangroves and sea-life!Tropical Oasis is a two bedroom, two bath...

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$355
avg per night
Big Pine Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

You and your family will feel right at home in this charming Big Pine Key home. The Owners have totally refurbished this 2 bedroom plus den, 2 bath property in 2020. Soft sea colors and coastal décor make this a totally comfortable home away from home.Large and spacious living room, kitchen and...

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$172
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Tiki Time! Private Pool~Tiki Hut~Kayaks~Grill~Ocean View!Tiki Time ~ your private paradise in beautiful Marathon, heart of the Florida Keys! This is the perfect place for a family vacation or relaxing getaway. Gorgeous 3BR home with your own private salt water pool, Tiki Hut, space to park a 30′...

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$297
avg per night
Key West House
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Welcome to Island Paradise, your serene retreat in the heart of Key West, Florida! Located in Old Town, Island Paradise is just a half block from the world-famous Duval Street. This charming property offers 2 bedrooms and 2 bathrooms, perfect for small families or couples looking for a relaxing and convenient...

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$154
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool

About this property

Escape to paradise at our stunning 3-bedroom, 2-bathroom pool home, perfectly situated to offer breathtaking open Gulf views. This inviting retreat is designed for relaxation and enjoyment, making it the ideal getaway for families or friends seeking the ultimate Florida Keys experience.Highlights:Breathtaking...

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$442
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Seaside SerenityWelcome to your exclusive luxury retreat in Marathon, Florida. Seaside Serenity is a brand-new, 4-bedroom 4.5-bathroom, private pool home where paradise meets perfection. With 35' of dockage and nestled in close proximity to the Atlantic Ocean, Gulf of Mexico, and Coco Plum Beach,...

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$728
avg per night
Special Offer
Islamorada House
Sleeps 10, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

This quaint Keys-style home offers timeless charm in a premier waterfront setting on an ocean-access canal. The open-concept living, kitchen, and dining area flows effortlessly through the terrace to the backyard, where a private dock invites boating and fishing, and an outdoor bar and dining area offer...

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$399
avg per night
Marathon House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Tropical Canalfront Retreat Near Sombrero Beach – 2 Bed / 2 BathEscape to paradise at this beautifully appointed 2-bedroom, 2-bathroom vacation home located in the heart of Marathon, Florida. Nestled on a deep, wide canal, this waterfront getaway offers the perfect blend of comfort, convenience,...

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$307
avg per night
Key Largo House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi
$179
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Emerald HorizonExperience elevated coastal living in this luxury 5-bedroom, 4-bath vacation rental in Marathon, Florida Keys, designed for large families and groups seeking premium comfort, modern design, and Gulf-access adventures. Located in the new community of Emerald Flats, this home includes...

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$598
avg per night
Key Colony Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to tranquility in this charming two-bedroom, two-bath half duplex located on the shaded side of 9th St. Newly installed, the sparkling 9 X 16 pool offers a relaxing oasis with therapy jets in the seating area. Indulge in comfort with a king-size bed in the master bedroom, while the guest bedroom...

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$274
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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$187
avg per night
Little Torch Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Reel Life, a beautiful Cudjoe Gardens Oasis! Located on the ocean side of Cudjoe Key, this home has everything you need to enjoy a true Florida Keys vacation! It features an in-ground heated pool, a large Tiki hut/bar for hanging out by the pool, a wood dock to accommodate your boat, a sandy...

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Featured review

"back country fishing"

I have been going here for years. We enjoy fishing the back country, and it is right on the gulf. It is a great time to get to enjoy family.

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$297
avg per night
Marathon Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This charming property offers 3 bedrooms and 2 bathrooms, ideal for families or groups looking to enjoy the beauty and tranquility of the Florida Keys.*Saturday-to-Saturday Rentals OnlyProperty Overview:Prime Location: Bird of Paradise offers stunning views of the Atlantic Ocean. Bird of...

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$270
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Fresh, clean, updated and excellent deepwater boating with expansive canal views is what you will find in our newest addition to our Coco Plum Beach neighborhood! Just minutes down the bike path to sandy Coco Plum Beach! This 3 bedrooms 2 bathroom home is just what you've been looking for in a vacation...

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$249
avg per night
Islamorada House
Sleeps 12, 6 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Mile Marker 77 – Oceanfront – Lower Matecumbe Key.Six bedroom/ four bath luxurious oceanfront premier rental estate on Lower Matecumbe Key in Islamorada. Enjoy a walk around the lush, native garden or take a dip in the oceanfront pool. Catch palm tree shade or sun on the private beach,...

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$573
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Emerald TidesWelcome to Emerald Tides – a brand-new luxury vacation rental in Marathon, Florida, located in the exclusive Emerald Flats community. This oceanfront escape offers breathtaking open water views of the Gulf of Mexico, a private pool, premium dockage, and upscale interiors that reflect...

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$695
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Paraíso Del MarIntroducing our newest luxury vacation rental nestled in the prestigious community of Marathon. This brand-new build epitomizes elegance and sophistication, offering an unparalleled experience for those seeking the epitome of luxury in the Florida Keys.Set amidst lush tropical...

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$978
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The Toasted Coconut ~ your private paradise in beautiful Marathon, the heart of the Florida Keys! Gorgeous 3BR home. Your own private pool, gas grill, bikes, beach chairs, all await you for your beautiful day in the Florida Keys! Less than 10 min to Sombrero Beach, Dining & Local Bars. We have everything...

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$252
avg per night
Last Minute Deal
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
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...

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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...

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Key West House
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 1 miles to Fort Zachery Taylor State Park

Key Amenities

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

About this property

924 Southard Street... an Old Town cottage made famous by Country Home magazine! Featured in Country Home , in June 2001, this one-of-a-kind cottage was formerly owned and decorated by well known decorator Mary Emmerling. Southard Comfort is perfect for the guest who wants to feel like a local and enjoy...

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Featured review

"Just Perfect"

Southard Comfort is perfectly appointed and comfortable. There is nothing I can suggest to improve the experience. The house is nicely decorated, the kitchen is completely outfitted, the location is great...

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$228
avg per night
Little Torch Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 5 miles to Bahia Honda State Park

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Ground floor 3/2 with garage, lanai, and deep water dock. Great area for fishing, lobstering and boating. Bahia Honda beach and park 8 miles away. 28 miles to Key West. Home features a separate dining room, living room and fully equipped gourmet kitchen. Equipment shed separate from home for fishing,diving...

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Featured review

"Beatiful place to stay"

Jeanette and Dave's property was a very, very nice place. It was much larger on the inside than it looks from the outside. Absolutely nothing to complain about with this property.

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$180
avg per night
New
Cudjoe Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Welcome to Palms & Pina Coladas where you will enjoy a beautifully remodeled waterfront paradise. Located in coveted Cudjoe Gardens, this ground level home comes equipt with everything you need for a relaxing Florida Keys Vacation! Private heated & cooled in-ground pool, fenced yard, 80 ft of...

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$325
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...

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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...

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$315
avg per night
Big Pine Key House
Sleeps 5, 2 bedrooms, 1 bathroom
3 reviews

Key Amenities

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

About this property

Stay where the palm trees meet the ocean. The Egret House is a quaint and charming home nestled in the lower Florida Keys. This spectacular home is in the perfect location in the highly desirable side of the island. Cozy 2 bed, 1 bath property with open water access, heated and cooled saltwater pool,...

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Featured review

"Wow, just Wow"

We stayed from middle of June to middle of July this year and can tell you, you will not find a more relaxing vacation spot that this one. Scott was incredible from the first day we connected until we...

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$433
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Peace at 7 Knots... The newest house on Sombrero Beach Road! Be the first to stay at our lovely home. It is wonderfully decorated with a "more is less" clean style while at the same time having all that you will need in a single family home located in Marathon. Whether you are vacationing with...

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Featured review

"Great week in Marathon"

Had a great stay at this property. House is wonderful. Everything we needed was there! Ice machine outside for fishing came in very handy. House is clean and nice, outside is very nice with pool tiki hut...

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$500
avg per night
Key Largo House
Sleeps 12, 5 bedrooms, 6 bathrooms

Key Amenities

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

About this property

YOU ARE JUST ONE STEP AWAY FROM A DREAM VACATION IN THIS ONE OF A KIND CUSTOM HOUSE. IT FEATURES A HEATED POOL AND 100' DOCK. LOCATED ON ADAMS CUT , THIS LUXURIOUS PROPERTY HAS 5 BEDROOMS ( 4 LARGE MASTER SUITES ) AND 6 FULL BATHROOMS. EACH OF THE 4 MASTER SUITES HAS A PRIVATE BATHROOM AND LARGE...

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$680
avg per night
Islamorada Condo
Sleeps 8, 3 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Mile Marker 83 – BayfrontWelcome to your dream waterfront rental home in Islamorada, located in the heart of the Florida Keys. This stunning 4 bedroom, 4 bathroom home sits on the bay and offers breathtaking views of the water and world class sunsets.As you enter the home, you’ll...

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$733
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Introducing Maison Residences Unit 201, Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE —A world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean...

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$1,255
avg per night
Big Pine Key House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

3bd 3bath Icemaker Deep freezer Dock Water access

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Marathon House
Sleeps 10, 5 bedrooms, 5 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to 137 Mockingbird Cove! Modern, expansive home built in 2022, offering incomparable boating! Quick walk or ride from Sombrero Beach. Each of the 5 bedrooms features its own ensuite bathroom, offering ultimate privacy and comfort. Includes a private heated/chilled pool, 2 paddleboards, 4 bicycles,...

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Featured review

"Beautiful Sombrero Beach area house with pool."

Spacious 5 bedroom/bath house near the beach, shopping, and restaurants. Tastefully decorated and comfortable beds.

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$857
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
24 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, pickleball, heated pool, private beach, and dockage for...

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Featured review

"Very Good place"

We stayed in unit 102. Glenn was a great guy to rent from, very helpful and followed up for any questions.a very nice condo, private bathroom for two main bedrooms. Most everything needed for making meals...

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$187
avg per night
Summerland Key House
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Distance to beach: 6 miles to Baja Honda

Key Amenities

  • Air conditioning
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

Conchcanary is located on Little Torch Key, in the heart of the Florida Keys. Come relax in our hammocks with a tropical beverage or bring your boat for some fantastic fishing.Enjoy your morning coffee with a canal views from the screened balcony. Newly updated kitchen with top of the line appliances,...

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Featured review

"Honeymoon in the Keys"

My wife and I spent the first 7 days of our married life living it up in the Keys. We loved it. Kayaking in the bay. Trips to the beach (very different from other beaches). Snorkeling in the ocean! Live...

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$183
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.