Florida Keys Vacation Rentals

(408 rentals)
Reel Life. 4/3 Private Pool, Private Dock, Bikes, Kayaks!

$469

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This beautiful 4 bedroom, 3 bath home is less than 2 minutes from Sombrero Beach just down the street (oceanfront) and less than 15 minutes to open water! Private pool with outdoor tv on the patio, private dock, 2 bikes, 2 kayaks, bait freezer, gas grill! The private dock can accommodate up to a 40' boat. ...

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Property Type

Marathon House

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Ma761

2 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 3 miles to Coco Plum Beach

$234

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Fishing Paradise……Two bedroom, two bath home in a great boating location! Just one canal in from the Gulf and very close to Vaca Cut. Fish cleaning table, bait freezer, 75' of dockage, hi speed internet, washer/dryer.Cute home with a King size bed in the master, 1 Queen and 1 twin in ...

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Property Type

Marathon House

"Perfect relaxing and quiet get away"
Reviewed January 30, 2021

We enjoyed the pool and the quiet pool area that was so nicely decorated and had everything we needed.The house was very homey and had all the amenities that you could ask for. Location is perfect ...

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Waterfront/Open Gulf Access/Dock/Pool/Spa/Wraparound Deck

$328

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

With quick, easy access to the Gulf and Atlantic Ocean, this home is perfect for fishing, snorkeling and boating. This three-bedroom, two-bath home, which sleeps eight, has a 45-foot dock with ample room for your boat. It is only one house away from the mouth of a deep-water canal that leads directly ...

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Property Type

Marathon House

"Quiet and cozy"
Reviewed September 21, 2020

House had plenty of parking. Dock was great for our boat. Easy access on and off boat. The hot tub and pool is where we were if we were not on the boat. House was very clean. Will stay here again.

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GROUPER THERAPY

3 BR | 2 BA | Sleeps 6 | Quick View

$144

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

You will be pleasantly surprised when you arrive at Grouper Therapy on Little Torch Key. One of the few ground level vacation homes. No steps here!!Nicely styled kitchen with granite counters and newer appliances and a small breakfast bar to enjoy morning coffee and snacks.The living area is roomy ...

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Property Type

Little Torch Key House

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Oasis in the Keys. Oasis in the Keys! 3 BR 2.5 BA Direct Ocean Front!

$429

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Boasting stunning floor-to-ceiling ocean views in every room, this newly remodeled 3BR/2.5BA home promises a delightful oceanfront stay in the Florida Keys. Use the four provided kayaks, two paddleboards for fun-filled explorations, or hop on the bikes to cruise the surrounding area. Enjoy a game of shuffleboard ...

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Property Type

Marathon House

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Waterfront Hideaway: Quiet Locals Experience with Dockage!

2 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 3 miles to Sombrero Beach

$141

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Peace and Quiet in the heart of Marathon!This house is a 2 bedroom, 1 bathroom waterfront half duplex. There's a screened in porch, so you can relax in comfort on the water. The house has 24' of dock space that you can leave your boat parked at and room for a trailer in the driveway. There's a BBQ ...

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Property Type

Marathon House

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The 6 bedroom Duval Street Compound

6 BR | 7 BA | Sleeps 16 | Quick View

2

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1389

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on ...

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Property Type

Key West Villa

"Best place we have ever stayed!"
Reviewed August 1, 2020

What an amazing 6 bedroom property in the heart of Old Town Key West. We did not move the car once, We would not rent one next time as you can walk to everything. It is all so close. The pools were simply ...

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Poolside Palms

2 BR | 2 BA | Sleeps 5 | Quick View

$273

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool

About this property

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and ...

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Property Type

Key West Condo

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August 14-21 Available * DIRECT PRIVATE BEACH FRONT 2/2 Condo Key Colony * Pool

$240

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

$1,500 - $2,000/wk., depending on season. 7 night minimum stay. Saturday-to-Saturday only during high season.*** Reservations accepted with the contingency that they comply with the Monroe County Directive, and subject to the rules and requirements thereof. If evolving rules and requirements subsequently ...

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Property Type

Key Colony Beach Condo

"Wonderful"
Reviewed December 17, 2020

I cannot thank the owner enough. This place is even better than imagined. Everything about this rental was flawless, from the rental manager to the condo. We can't wait to return.

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Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

$279

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

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

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Property Type

Islamorada Condo

"Gorgeous place"
Reviewed November 22, 2020

Thank you so much for letting us stay at your condo! It is absolutely gorgeous and you have everything there we needed and more. The location was perfect and our children enjoyed the tennis courts, pool, ...

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Ma1000 235 Sombrero Beach Road Marathon, Fl 33050

$452

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Newer and nicer than most. This lovely 4 bedroom, 3 bath will be a very comfortable spot for you to call home away from home. Pleasantly decorated with large covered porches, hi-speed wireless internet, 4 flat screen TVs, fish cleaning table and bait freezer. There are two complimentary kayaks (two-man) ...

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Property Type

Marathon House

"Plush enough for the workaholic"
Reviewed January 15, 2021

The house was very well decorated, it gave you a feeling of newness and class. Everything was taken care of down to the last detail of having spices in the cabinet. My family would recommend this place ...

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Cockadoodledo Vacation Rental. Featured On Hgtv***multiple Month Discount***updated

$321

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Cock-a-doodle-do Vacation Rental, named for Key West's beloved chicken population, is a mid-town oasis! 5 minute drive to Old Town or take Uber for just $10!A meticulously updated pool home with beautifully lush landscaped grounds and plenty of space for everyone! The main house is a 3/3 (1 King, ...

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Property Type

Key West House

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Family Gatherings

5 BR | 4 BA | Sleeps 14 | Quick View

Distance to beach: 1 miles to Cabana Club

$614

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

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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Property Type

Key Colony Beach House

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Keys to Paradise

3 BR | 2 BA | Sleeps 8 | Quick View

$286

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Private Pool

About this property

3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride to all that Key West has to offer. Keys to Paradise will not disappoint. Direct ocean front condo that features 1 master suite with a king size bed, jacuzzi and luxurious walk in shower. ...

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Property Type

Key West Condo

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MA976 938 92nd Street 0cean Marathon, FL 33050

3 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 4 miles to Sombrero

$434

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront

About this property

Single Family Home fully updated with everything you will need for a perfect vacation. The master suite has a king size bed with an ensuite bath. The ensuite bath has his and her sinks, lovely, large shower and bidet. The 1st Guest Bedroom has 2 Queen size beds and it's own ensuite bath. There is also ...

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Property Type

Marathon House

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Oceanfront Luxury "Mar Azul"

3 BR | 2.5 BA | Sleeps 6 | Quick View

6

$443

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

A relaxing executives delight -High-end Estate overlooking tranquil 'Bonefish Flats' in picturesque Marathon. Designer decorated with contemporary colors, loads of fine architectural details, Crema Marfil marble, Granite, Hardwood floors, open air porches and balconies. This is a superb, secluded estate, ...

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Property Type

Marathon Estate

"Mar Azul was wonderful"
Reviewed January 24, 2021

Mar Azul was exactly as billed. It was spotless and very relaxing. The rooms are well appointed and the house and pool are quite private. We rented SUPs and had them right on our dock to use every day in ...

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Deep wide canal, ocean view, unlimited dockage.

$149

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Rentals by Owner

About this property

Sea horse 1: Deep wide unlimited dockage with 50 amp power by the dock, flow through canal, View of Vaca Cut & Atlantic Ocean. Swimming , snorkeling, fishing all right from the dock and swim with beautiful Tropical fishes and manatees! Tastefully decorated & furnished, cute & clean, ...

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Property Type

Marathon House

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Ramrod Key

2 BR | 2 BA | Sleeps 6 | Quick View

2

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

$130

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

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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Property Type

Ramrod Key House

"Hidden gem in Ramrod keys!!"
Reviewed March 5, 2021

AFTER STAYING HERE FOR THE MONTH OF JANUARY WE KNEW WE PICKED THE PERFECT SPOT. WE LOVED THE FACT WE COULD GO TO KEY WEST IN 25 MINUTES AND LEAVE THE CRAZIES BEHIND AND GO TO OUR OWN QUIET HOUSE. THE BICYCLES ...

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Keyhole: 3 BEDROOM VACATION RENTAL

$418

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Three bedroom, two bath home with an additonal den for extra sleeping. Nice patio facing the canal with 50' of dockage. The master bedroom has a king size bed, separate sitting area and it's own bath. the den is also on this level with a hideaway couch that opens up to two twins. Downstairs there are ...

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Property Type

Marathon House

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LITTLE BAY - Upper Duplex -A 2nd Floor Duplex on Gated Bayfront Shared Property

$429

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

Minimum Rental: 7 Days Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit sleeps ...

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Property Type

Islamorada House

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Waterfront, 75ft dock, Sombrero Beach 2.5mi, WALK to stores & restaurants

$293

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

Come enjoy tranquil breezes from the Atlantic Ocean sweeping through the grounds of this spacious duplex property on 7,500 sq ft of recreational space waiting for all your island fun & games. The rental offers 1,200 sq ft boasting three (3) spacious bedrooms and two (2) bathrooms both with full tubs. ...

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Property Type

Marathon House

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GONE FISHING

3 BR | 2 BA | Sleeps 6 | Quick View

$183

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

”Gone Fishing” is exactly where you will be during your vacation time at this pristine home on Summerland Key, just 23 miles to Key west and 25 miles to Marathon.Relax and enjoy cocktails and snacks by the heated and chilled swimming pool after a great day exploring all the treasures the ...

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Property Type

Summerland Key House

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Tingler Retreat. 100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

$567

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This newly renovated tastefully decorated 3 bedroom, 3 bath home with a pull-out couch has a peek-a-boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground level with plenty of natural light and a fully fenced yard! Available for guest use are 2 bikes, ...

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Property Type

Marathon House

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Palm Breezes

5 BR | 3 BA | Sleeps 12 | Quick View

1

$606

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1. Located just 20 miles away from Key West. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Downstairs grill, upstairs grill, Jacuzzi. Full WiFi. TVs in every ...

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Property Type

Cudjoe Key House

"Amazing find!!!"
Reviewed November 24, 2020

Amazing home in Cudjoe Key!! Only 20 minutes from Key West! Prime location, wonderful home with all the amenities. We had 9 of us and loved having the pool, jacuzzi and kayaks to use! Great restaurants ...

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Searenity Vacation Rental! Pool, Tiki Hut, Dockage

2 BR | 2 BA | Sleeps 8 | Quick View

1

Distance to beach: 5 miles to Coco Plum Beach

$345

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

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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Property Type

Marathon House

"Searenity !"
Reviewed February 15, 2020

One Month of pure bliss ! From the moment we walked in to the Dolphin Drive home we fell in love ! We felt immediately comfortable and at home ! Clean , spacious with every amenity needed for your home ...

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Waterfront Get Hooked

4 BR | 3 BA | Sleeps 10 | Quick View

4

$433

avg/night

View Details

Key Amenities

  • Air Conditioning

About this property

Waterfront Home in the heart of the Florida Keyes. Come relax and enjoy the beautiful waters of Sombrero and Bahia Honda Beaches. Both nearby. There is plenty of room and comfort in our 4 bedroom, 3 bath home. Two King Master Suites with attached baths. Satellite Flat Screen TV's in each bedroom. Fully ...

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Property Type

Marathon House

"Perfect Getaway"
Reviewed March 8, 2020

What a great place! Has everything you need to feel at home! We stayed the entire month of February 2020 and had an absolutely wonderful time. George is awesome and so responsive to any of the questions ...

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BOAT, POOL & BEACH HOUSE-Unity & Autonomy BOTH sides of upstairs Duplex/70' DOCK

$257

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

ALERT: BRAND NEW POOL JUST COMPLETED AND INSTALLED....This listing is for BOTH sides of the duplex the whole house can be rented through here so that you can Enjoy the keys life in style living in this beautifully furnished 4 Bedroom (2 on each side), 2 Bath (1 on each side) , 2 kitchens (1 on each ...

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Property Type

Islamorada House

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SUNKISSED

2 BR | 1 BA | Sleeps 5 | Quick View

$107

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Sun Kissed you’ll be during your stay at this wonderful home on Ramrod Key!This newly remodeled, tastefully decorated home offers both comfort and style for sun worshippers and fishermen alike. The two bedrooms and two baths have all new comfortable beds, bedding and linens. The living room ...

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Property Type

Summerland Key House

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ALOE HOUSE

3 BR | 3 BA | Sleeps 6 | Quick View

$159

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Make your memories at the Aloe House on Cudjoe Key! This home is located on a beautiful crystal clear canal with plenty of dockage for up to a 25 foot boat. The canals here provide great access to some of the best fishing in the Florida Keys. Enjoy boating, fishing or kayaking right from your back door.After ...

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Property Type

Cudjoe Key House

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W09 - 2394 Coco Plum Dr Unit 3

6 BR | 6 BA | Sleeps 14 | Quick View

$982

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Brand new construction built in 2019. Be one of the first to stay in this luxury home.6 Bedrooms 6.5 BathroomsWelcome to paradise! Escape to this luxurious six bedroom home designed for VIP guests. Across the street from open water, with beautiful views! Each bedroom includes an en suite bathroom. ...

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Property Type

Marathon House

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Best Views on Long Key

2 BR | 1.5 BA | Sleeps 4 | Quick View

$135

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

Enjoy Beachfront Island Life from our home on the water. We are literally only 10-20’ from the water depending on the tide.Huge wrap around balconies on both levels and another balcony on the back side overlooking tennis court and gardens.Fall asleep to the sounds of waves lapping on ...

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Property Type

Long Key Condo

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Upscale Home in Truman Annex!

1 BR | 1 BA | Sleeps 3 | Quick View

3

Distance to beach: 0.3 miles to Ft. Zachary Taylor

$198

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool

About this property

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and ...

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Property Type

Key West Condo

"Paradise"
Reviewed September 29, 2020

We loved the location of this rental. Everything inside the rental was as should be. I could not complain about anything but only say that i cant wait to return. We were a couple of blocks away from everywhere ...

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Beautiful Townhouse Awaiting Your Tropical Escape

2 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.3 miles to Ft. Zachary Taylor Beach

$305

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool

About this property

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and ...

View all property information

Property Type

Key West House

"Kokomo Korner"
Reviewed February 1, 2021

Excellent location. Short walk or bike ride to Duval for shops and restaurants. Outdoor patio space is large, private and perfect for morning coffee or evening cocktails. Overall condition of the property ...

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BARBADOS LANDING

2 BR | 2 BA | Sleeps 4 | Quick View

$152

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

On vacation but right at home in this newly remodeled two-bedroom, two-bathroom canal front home! Your boat will also feel at home on the 30’ dock. Relax on the open porch overlooking the canal or in your spacious, bright and airy living room.Cook your catch of the day on the charcoal grill ...

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Property Type

Summerland Key House

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Hidden gem 2/2 villa, stunning waterfront views, boat ramp & free dockage!

2 BR | 2 BA | Sleeps 4 | Quick View

10

Distance to beach: 5 miles to Anne's Beach

$275

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Rentals by Owner

About this property

2 Queen Beds, sleeps 4 + (1 Bedroom / 1 Murphy Bed)/ 2 BathroomsDock your boat up to 26 ft.The "Nest" is located bay-side at Mile Marker 82.3 in beautiful Islamorada. The Villa is a privately owned condo residence (one of only 7 units) which is wonderfully maintained and a true hidden ...

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Property Type

Islamorada Condo

"More than a gem"
Reviewed January 2, 2020

The home was exactly as described but better. Every detail was attended to including instructions on how to use everything right down to the remote controls. Exceptional use of space with comfortable ...

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Kens Conch Key Cottage - Optional motor boat rental - Pay direct to owner site

2 BR | 2 BA | Sleeps 5 | Quick View

1

Distance to beach: 4 miles to Long Key or Curry Hammock

$290

avg/night

View Details

Key Amenities

  • Air Conditioning

About this property

*****Booking on Pay Direct to Owner sites save you the most money!*******Kens Conch Key Cottage is a small romantic cottage in a quaint Old Florida Keys style Lobster fishing village, on a tropical island named Conch Key. We are located about 10 miles from Marathon and close to various state parks ...

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Property Type

Marathon Cottage

"Relaxation vacation"
Reviewed January 27, 2019

Our first visit to the keys was stress free with this cottage rental. From first inquiry to end of vacation, Ken made this so easy. The cottage had everything we needed. After a day of exploring it was ...

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MA876 122nd Street Ocean Marathon, FL

5 BR | 4 BA | Sleeps 12 | Quick View

1

Distance to beach: 3 miles to Coco Plum

$660

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Private Pool

About this property

Enjoy life at Serenity! Amazing home on the ocean with 137' of deep water protected dockage. Unobstructed views of Vaca Cut from this elegant home. Enjoy breathtaking sunsets, dolphins playing in your backyard, visiting manatees, fishing from your very own The dock has 137' of seawall , with water and ...

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Property Type

Marathon House

"Marathon House"
Reviewed December 15, 2020

The view at this house was amazing and the sunsets stunning! The kitchen is large and stocked with everything you need to cook. The Master bedroom is very spacious.

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Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow.

$224

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping, the main 2/2 house features an indoor/outdoor ...

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Property Type

Key West House

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Key Colony Vacation Rental by Owner

$171

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Tads Place has everything you need for your Keys Vacation. 30ft of boat dockage,ample parking for your boat trailer and vehicles.Full kitchen all towels and linens provided.Great out door sitting area and grill. Walk in freezer. Washer and Dryer and Cabana Club membership for pool.

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Property Type

Key Colony Beach Condo

"Great place to stay"
Reviewed January 6, 2021

Susan and Tad keep the place in great shape, a great experience. An the location is perfect, wide canal, safe neighborhood, pleasant people.

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Hidden Cottage

3 BR | 3 BA | Sleeps 6 | Quick View

1

$233

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

Down a very quite lane the house has one off street parking spot.Enter from gate through lush and colorful walk to front door of main house . Enter into the living room with smart tv ,through to the right into the dinning area. The kitchen is off to the left. There is a large working counter with seating ...

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Property Type

Key West House

"Perfect pet-friendly vacation cottage"
Reviewed March 2, 2021

The house is tucked away on a lane in Old Town within walking distance to everywhere. It is very private with lush plantings and a variety of outdoor spaces to sit. The house is well equipped and the owners ...

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Serenity at 1st Avenue Gulf Unit # 1

$600

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Brand new 5 bedroom, 4 bath single family home with 30′ of assigned dockage, 11 X 22 private pool that goes from 3.5′ to 5′ in depth. 2293 square feet of living area. Stunning views, with balconies to capture the breezes and the views. Lots of parking for your vehicles and boat trailer. ...

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Property Type

Marathon House

"Beautiful Home"
Reviewed March 14, 2021

We recently stayed at this beautiful furnished home. It was a great vacation with my adult children and granddaughter! The location was perfect with restaurants, shops and beaches. The pool was perfect ...

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Breathtaking Ocean Front- Pristine Beaches- Luxurious Condo!

$281

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Pool

About this property

From the first moment you enter this luxurious condo, you will be speechless at the Panoramic Oceanfront view. This 2 bedroom end unit sits on the top floor of the prestigious Monte Christo and features a spacious open floor plan decorated with high end contemporary furniture, gourmet kitchen, 2 large ...

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Property Type

Key Colony Beach Condo

"Hidden Gem!"
Reviewed October 19, 2020

My stay at KCB was amazing. We had our own private beach and pools. This is the perfect place to get away from the virus because there were so few people and all of the facilities were clean. The apartment ...

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ANOTHER DAY IN PARADISE

3 BR | 2 BA | Sleeps 6 | Quick View

$236

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

It’s more than just another Day in Paradise, it’s an incredibly wonderful and memorable vacation stay in the fabulous Florida Keys!Please come stay with us in this large 3 bed 3 bath heated and chilled pool home on deep water canal in Summerland Key. Entering the home by way of the 2 story ...

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Property Type

Summerland Key House

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Gorgeous waterfront home

3 BR | 2.5 BA | Sleeps 8 | Quick View

$650

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Beautiful, fully remodeled waterfront home with water on both sides! Ocean and lagoon views from bedrooms, dining room, balconies and kitchen. Cable TV with premium channels and wi-fi internet access. The home is in a quiet neighborhood on a cul-de- sac and very convenient to Tavernier or Islamorada ...

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Property Type

Islamorada House

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Ma870

3 BR | 2 BA | Sleeps 8 | Quick View

1

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Have a truly blissful vacation at this charming, Gulf Front home that sits on one acre of pristine property on exclusive Morton St. Enjoy the magnificent open Gulf views from nearly every room. This unique home is reminiscent of the way the Keys used to be…..charming! Perfect area for walking, ...

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Property Type

Marathon House

"Great house!"
Reviewed December 4, 2020

Everything from the location to the layout of bedrooms was perfect! The house is walking distance to a cute little coffee shop, fishing bait, snorkeling, gas station, shops, etc. We fished off the dock ...

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Sombrero Beach Rentals, House with Pool~Spa~Boat Dock~ walk to Sombrero Beach!!!

$1447

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Great for Family Reuions, and Large Groups vacationing in the Florida Keys! Fabulous 6500 sq ft. vacation paradise. Includes everything you need for a perfect Family Reunion or large destination vacation.Private Vacation Rental Waterfront Home with 6 Bedroom 5 Baths Private Pool and Spa ~ Private ...

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Property Type

Marathon House

"Look no further!"
Reviewed April 3, 2021

Seriously, there is nothing our family wanted for at this property. Liz and Captain Bob were great, providing us with bikes, sand volleyball, bags, an amazing dock...but the highlight was the outdoor kitchen! ...

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Luxury Oceanfront Home, New Rental, Views, Pool

4 BR | 4.5 BA | Sleeps 8 | Quick View

1
Owner special: May 1-8 Now $4,900/wk Discounted $1000 off

$846

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

‘The Beach House’ at Tarpon Point in Islamorada‘The Beach House’ is a luxurious oceanfront home in a private gated enclave of only 12 houses. This end home offers privacy and beautiful ocean views including of Indian Key Historic State Park. Enjoy morning coffee and a phenomenal ...

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Property Type

Islamorada House

"The Perfect Escape"
Reviewed April 1, 2021

We could not have been happier at this exquisite home. It was clean, in a great location, and the pool was awesome! The marina across the street is within walking distance and they have food, shopping, ...

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Suite 16 at Key Colony Point Condominium Complex CORNER UNIT- BEST VIEWS!

3 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.0 miles to Walk downstairs!

$339

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

Located at the southernmost point on Key Colony Beach, Suite 16 is virtually surrounded by the beautiful turquoise waters of the Atlantic Ocean. This spectacular Key Colony Point condo offers panoramic views of Florida Keys ocean waters and sunshine from almost every room. Floor to ceiling windows in ...

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Property Type

Key Colony Beach Condo

"Fabulous place"
Reviewed June 14, 2019

Oh what a great place for a vacation. Everyone is so friendly and helpful and the view is outstanding. Beautiful beach, great restaurants with delicious fresh seafood. Yum. Lots to do and I can't wait ...

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LITTLE BAY - Lower Duplex - Ground Level Unit on Gated Bayfront Shared Property

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Founders

$429

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

Minimum Rental: 7 Days Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up ...

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Property Type

Islamorada Apartment

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Dockside Retreat. Canal Front, Tiki Hut, Kayaks, Bikes, Pool, Beach!

$469

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Dockside Retreat! Rent one side or both! This 4 bedroom 3 bath canal front home has a private pool, private dock, fish cleaning station, green light under at the dock, two kayaks, two bikes, and a Tiki Hut for the ultimate Keys vacation! With plenty of parking for vehicles and a boat trailer, a well-stocked ...

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Property Type

Marathon House

"Family Vacation"
Reviewed January 11, 2021

This rental has it all for a large group! The beds are very comfortable, the kitchen is stocked with everything you need, and the pool area with the tiki hut offers hours of enjoyment for kids and adults. ...

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Florida Keys Vacation Rentals