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Florida Keys Vacation Rentals

(588 rentals)
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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$302
avg per night
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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$276
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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$600
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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$278
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 1.5 bathrooms
5 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 Views, Beautiful Condo, Perfect Getaway Spot"

Loved this condo! Amazing views, tastefully furnished, everything we needed was already onsite. Host was very friendly, helpful. Perfect getaway.

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$275
avg per night

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Marathon House
Sleeps 10, 5 bedrooms, 4 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The Villa overlooks Boot Key Harbor with its beautiful sunsets to the West and refreshing breezes from the East that travel down Sisters Creek, a natural waterway that leads to great diving and fishing grounds of the Atlantic. Across Sisters Creek there is a natural preserve and no neighbors. It is private,...

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Featured review

"Great place to stay!"

We really enjoyed the house, very well appointed! 5 kayaks for you to use anytime , and believe me we used them and had a blast! Debra the owner is a dream even had a Bottlle of Champaign and a cake waiting...

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$647
avg per night
Key Largo Villa
Sleeps 6, 3 bedrooms, 3 bathrooms
7 reviews

Distance to beach: 0.0 miles to 4 small beaches on site

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Pool
  • WiFi

About this property

3 bedroom, 3 bathroom Ocean Front / Beach Front Villa in Key Largo sleeps up to 6. It was completely renovated in 2020. It has dockage for boats up to 38 feet. This Villa is 35 feet from the Ocean and has a private beach 5 feet from the patio. I provide a Golf Cart, Kayaks, PaddleBoards, Fishing equipment,...

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Featured review

"Great Location, Great Host"

This is a gated condo complex right on the water. We watched the teens snorkel in the little bay right from our balcony at high tide (be sure to do the stingray shuffle, there were a lot of them!) and used...

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$497
avg per night
Ramrod Key House
Sleeps 6, 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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$331
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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$260
avg per night
Big Pine Key House
Sleeps 13, 5 bedrooms, 4 bathrooms
4 reviews

Key Amenities

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

About this property

Welcome to our 5 bedroom with optional 6th bedroom home, “Reel’em Inn” Big Pine Key, an excellent location for a relaxing vacation with family and friends 31 miles from Key West’s Mile Marker 0. This spacious 5-bedroom home is on a double lot with plenty of parking and 150 feet...

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Featured review

"We love this place!"

We've stayed in this home for a month for 3 years, 2025 being our 4th year we added a month. We stayed in the home before Jeff and Christine bought it and loved it then. They've made so many improvements...

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$400
avg per night
Tavernier House
Sleeps 8, 4 bedrooms, 3 bathrooms

Distance to beach: 4 miles to Founders Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Island Time!This newly constructed canal front residence located in the heart of Plantation Key is sure to help boost your serotonin and ensure complete relaxation. This impressive home can comfortably accommodate eight adults with four bedrooms and three bathrooms.The main living...

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$513
avg per night
Key Largo House
Sleeps 7, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • 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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$400
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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$330
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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$467
avg per night
Last Minute Deal
Islamorada House
Sleeps 8, 4 bedrooms, 3 bathrooms

Distance to beach: 3 miles to Founders Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Blue Palm Oasis!Escape to paradise at Blue Palm Oasis, a charming 4-bedroom, 3-bath home located on Plantation Key in Islamorada. This contemporary Keys villa seamlessly blends modern comfort with laid-back island charm, making it the perfect place to unwind, recharge, and soak up the sun....

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$518
avg per night
Islamorada Townhome
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Escape to paradise in this gorgeous 3-bedroom, 3-bathroom townhome is located at Executive Bay Club in Islamorada, FL. Ideal for family getaways or group vacations, this townhome offers two luxurious king beds and a trundle bed in the loft, ensuring ample space for everyone.Enjoy breathtaking ocean...

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$230
avg per night
Islamorada House
Sleeps 18, 9 bedrooms, 8 bathrooms

Key Amenities

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

About this property

Welcome to Infinity Bay Islamorada – an infinite paradise with endless possibilities in the heart of the Florida Keys. This exclusive estate embodies sophistication and serenity, where guests can unwind in style against a backdrop of Florida Bay and swaying palm trees. At Infinity Bay, luxury meets...

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$1,867
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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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
Marathon House
Sleeps 8, 2 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 5 miles to Coco Plum Beach

Key Amenities

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

About this property

Searenity was just recently renovated and is a brand new ground level vacation rental! A direct shot to the Gulf in about two minutes and nestled in a nice quiet neighborhood on Dolphin Drive in Marathon, this home is in a great central location, not far from Publix Supermarket, all the restaurants and...

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Featured review

"Home away from Home"

I can’t stay enough. This place felt like home. Definitely coming back! Beds were so comfy, pool was definitely a plus after a day on the water - Neighbors were respectful-location is right on & owners...

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$365
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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$277
avg per night
Key Largo Townhome
Sleeps 6, 2 bedrooms, 2 bathrooms
5 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

"Great Unit and Excellent Host"

My family and I booked 9 days in the condo by the lagoon. I was a bit leery as there is a mix of good and not-so-good reviews for Norman. I found him personable and responsive on the phone whenever I...

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$289
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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$432
avg per night
Key Largo Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Experience the relaxed lifestyle of the Florida Keys. CLEANED AND SANITIZED TO THE NEW CDC STANDARDS. 3 Bedrooms + Loft, 2 Baths, Sleeps up to 8 comfortably. There are 2 large bedrooms on the 3rd floor, each with queen size beds. The first floor bedroom is small with 2 bunk beds. The 4th floor loft...

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Featured review

"Bit chaotic but overall very nice"

Property is very nice, we liked it lots. Resort is laid back & has lots of activities. I haven't done a resort holiday before so it was pleasant surprise to have free access to equipment like kayaks,...

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$322
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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$322
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Beautiful views from this condo!Bay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL.We are new owners of this condo that has never been in the rental pool. (that is why few reviews)Complete remodel with no expense spared!The location is quiet with the most beautiful...

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$668
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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$270
avg per night
Little Torch Key House
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

3 bedroom 3 bathroom home on canal with room for a 25' boatThis home is having a pool installed and will be completed in the Fall of 2021Master Bedroom: King bed with TV, private bathGuest Bedroom: Queen Bed with TV3rd Bedroom: Queen bed , sleeper sofa, Tv mini kitchenHall...

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$230
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
Little Torch Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

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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$201
avg per night
Islamorada Villa
Sleeps 14, 5 bedrooms, 4 bathrooms
1 review

Key Amenities

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

About this property

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

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$583
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2 bathrooms
6 reviews

Key Amenities

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

About this property

Private home located in New Town available for 28 day minimum rental. Beautifully landscaped yard with secure private back yard and pool. The home features a kitchen with all appliances and granite counter top. The master suite opens onto the pool deck and is furnished with a king size bed and walk-in...

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Featured review

"Excellent location,beautiful house,outstanding owners!"

We stayed a month in December(2022),had everything we needed,close to shopping,sightseeing, nightlife,beaches and airport. House is completely furnished and nothing is lacking.Pool was heated and had all...

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$150
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 West House
Sleeps 8, 4 bedrooms, 4 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.*Saturday-to-Saturday Rentals OnlyProperty Overview:Prime Location: Casa Rosa is situated in a picturesque neighborhood, just one block away from Key West's renowned Duval Street. Casa Rosa...

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$1,042
avg per night
Cudjoe Key House
Sleeps 6, 2 bedrooms, 3 bathrooms
2 reviews

Distance to beach: 15 miles to Bahia Honda

Key Amenities

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

About this property

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. We are 80 feet the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on...

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Featured review

"Nice Condo"

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

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$445
avg per night
Key West Cottage
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 800 yards to Ft. Zachary Taylor State Park

Key Amenities

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

About this property

Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private town home (one of only seven available for...

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Featured review

"Island Magic"

Great location! Great people! Very nice place that gave us memories of a lifetime! I’ll be returning soon!

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$467
avg per night
Marathon Apartment
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to paradise at this stunning 3-bedroom, 3-bathroom single-family home in Key Colony Beach! Nestled in a prime location, this spacious home offers everything you need for a relaxing and unforgettable getaway. Whether you're a boating enthusiast, a pool lover, or just looking to unwind in the...

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$457
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • 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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$385
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Paradise Palms! ️ This stunning 4-BR retreat has it all. Boating right from your private dock, easy open-water access, waterfront views, unwinding in your private heated pool Fire up the grill for a sunset BBQ, challenge friends to cornhole or game room fun, and set off on a kayak adventure...

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Featured review

"Great time"

We have a great vacation, the house fit our needs perfectly. There recommended places to visit and eat at were great. Had a small issue with the dryer, we called them and they responded quickly.

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$511
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Brand-new construction, expertly decorated single family home in Marathon. Whether you are vacationing with family, embarking on a fishing trip or looking to just relax Florida keys-style this is the perfect home for you. This spacious 1,800 square foot single-level stilt home offers 4 bedrooms, 3 full...

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$564
avg per night
Ramrod Key House
Sleeps 6, 2 bedrooms, 2 bathrooms
10 reviews

Distance to beach: 8 miles to Bahia Honda State Park in the keys

Key Amenities

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

About this property

Ocean access waterfront canal with 40’ dock and all the fixins. Looe key reef straight out canal. 2/2 house with nice size porch

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Featured review

"A MONTH IN THE KEYS! WHATS NOT TO LIKE!"

I was really worried house was going to be too small, as it is a 2 bedroom. We ended up having plenty of room. Beds were very comfortable and A/C would freeze us . Dock was plenty big for our 35’ center...

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$124
avg per night
New
Last Minute Deal
Key West Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Art-Filled 1,700SF 3BR/2BA Old Town Key West Home with 2 Decks, Pool, Parking,++Large art-filled, two story Key West condo boasts 2 large inviting bedrooms, including a king bed, queen bed, and large office or third bedroom for extra flexibility. Guests enjoy living and dining rooms, 2 full bathrooms,...

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$415
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. This house includes all the elements you need for an amazing vacation. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24'...

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Featured review

"Peace and Tranquility. Amazing sunrises and sunsets"

The location was exactly what I had hoped. It was secluded, but close to everything. The water views were worth every penny!

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$500
avg per night
Marathon House
Sleeps 10, 5 bedrooms, 10 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to paradise at Anglers End Estate the ultimate vacation getaway with unobstructed open water views and an indoor heated pool. This stunning property boasts 5 bedrooms, 3 full bathrooms, and over 3600sq ft of living space, making it perfect for family and friend gatherings. Enjoy the amazing, landscaped...

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$871
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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$449
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
23 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

"Great people at the Futura Yacht Club"

Great facility for those with a boat! Each slip has electric and water wash down. The people at the Futura will go out of their way to help with fishing spots ( thanks Brian), restaurants, attractions....

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$189
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Lovely home with lots of glass windows looking towards the ocean. 50 ' of dockage with instant ocean access. 12 Therapy jets in the 14 X 30 pool that ranges from 3' to 5' in depth. The pool overlooks the canal and the ocean. Pool heat is add'l if paid in advance, $200 or $250 on arrival. Three...

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$429
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Paradise Point! Indescribable Views! This stunning sanctuary offers Water Frontage on 3 sides giving over 180° of unparalleled Atlantic Ocean Views, Direct Ocean Access from your Private Dock, perfect for boating or fishing right from the backyard After a day on the water, unwind in...

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$661
avg per night
Marathon Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Pool

About this property

Welcome to Coastal Charm, your serene seaside retreat located in Marathon, Florida! This charming condo offers 2 bedrooms and 2 bathrooms, making it ideal for families, couples, or small groups seeking a relaxing getaway.*Saturday-to-Saturday Rentals Only Property Overview:Prime Location: Situated...

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Featured review

"Great Great Great!!"

This place was nice, quiet, clean and on a private beach. Had plenty of room and we sat out on the balcony for several dinners and had great ocean views. Loved the area it was in. Condo and town were really...

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$206
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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$189
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.