Florida Keys Vacation Rentals

(344 rentals)
Cockadoodledo

4 BR | 4 BA | Sleeps 10 | Quick View

$394

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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Waterfront Sgl Family Pool Home:60' Dock: Direct Ocean Access:Kayaks:Ocean

2 BR | 3 BA | Sleeps 6 | Quick View

5

Distance to beach: 1 miles to Sombrerro Beach

$584

avg/night

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Key Amenities

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

About this property

Lemon Key CottageWelcome home…Thanks to Hurricane Irma, we now have a beautiful newly renovated home! We've spent over $150K on a complete restoration and modernization. (check out the new pics) Lemon Key Cottage is absolutely stunning with new: bathrooms, kitchen, appliances, flooring, ...

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Property Type

Marathon House

"What a terrific place!"
Reviewed October 24, 2020

Great Pool, Great House, Great Location, everything is new and fresh! Wow we loved it!!! Wonderful hosts!

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Private House Facing the Ocean with New Heated Swim/Pool/Spa LOC LOC LOC

$250

avg/night

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Key Amenities

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

About this property

Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open from Aug.6th to April 1st. This is a spacious oceanfront home with breathtaking open water views! It is located on beautiful Ramrod Key 85 ft concrete seawall facing the priceless Atlantic ocean teaming ...

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Property Type

Ramrod Key House

"Unbelievable vacation"
Reviewed January 1, 2020

I wish I could give this property more than just 5 stars. Property owner was amazing and helpful. Owner was available to answer all my questions and more. This property was everything described and more. ...

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Ma1000 235 Sombrero Beach Road Marathon, Fl 33050

$429

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

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Futura Yacht Club Bayside Condominium and Marina Dockage, Islamorada

$195

avg/night

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Key Amenities

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

About this property

Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean via Snake ...

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Property Type

Islamorada Condo

"Awesome!!"
Reviewed February 10, 2020

Stayed at Futura Yatch resort for a week. Stayed in 106 and an amazing condo! No problems at all! Loved the location and pool was awesome! Thanks Rick and Carey! Will be back!

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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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Ma100 Great Price

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 1 miles to Cabana Club

$228

avg/night

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Key Amenities

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

About this property

2 bedroom, 2 bath half duplex across from the Par 3 golf course, tennis courts and the park. This is the right side of the duplex with a 42″ Flat Screen TV in the living room and DVD Player, and a 32″ TV in each one of the bedrooms. Newly decorated and fresh paint in good condition. This ...

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Property Type

Key Colony Beach House

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Waterfront 6 Bedroom 5 Bath 65' Deep Water Dock, Pool, Tiki Hut, Outdoor Kitchen

6 BR | 5 BA | Sleeps 14 | Quick View

1

Distance to beach: 0.1 miles to Sombrero Beach

$860

avg/night

View Details

Key Amenities

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

About this property

Waterfront 6 Bedrooms , 5 Baths, canal views. On the HIGHLY sought after Sombrero Beach !!!(We rent weekly only, and our Check-in is on a Saturday and Check-out is on a Saturday dates only so we can optimize our months.)Our houses are safe and clean because we disinfect them with the highest ...

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Property Type

Marathon House

"Paradise!!!"
Reviewed October 9, 2019

This house wonderful! Even better than the pictures. The layout allows for a large group. The outdoor kitchen is a gathering place. Many hours were spent relaxing at the hot tub and pool. Our 30 ft boat ...

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Truman Annex - ' Island Queen' End Unit Villa is One-of-a-Kind!

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Once you see this historic two storey townhouse, you won’t want to stay anywhere else!Filled with natural light, this end unit is ‘tucked away’ in an exclusive, historic Foundry building next to the ‘Truman Little Whitehouse’. There are only 3 residences in our building!There ...

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Property Type

Key West Townhome

"Great Winter Getaway! Wonderful! 5-Stars!"
Reviewed March 4, 2020

Yes, this end unit is "One of a Kind"! Many thanks to Rosemary & Mark. Their spacious, quiet & immaculate home has been our great winter escape. This was our third stay at this remarkable townhouse in ...

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Summerland Key Canal front 3 story pool Home

$200

avg/night

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Key Amenities

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

About this property

This home is the perfect escape in a wonderful neighborhood! Has a heated pool and large covered patio. The house is one street over from the most beautiful oceanfront homes. You will see the wooden boat go back and forth transporting guests to Little Palm Island.If you want to go to Key West it’s ...

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Property Type

Summerland Key House

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Key West Luxury Resort Home with pool

4 BR | 3 BA | Sleeps 10 | Quick View

1

Distance to beach: 2 miles to Smarthers Beach

$300

avg/night

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Key Amenities

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

About this property

Large 4 bedroom home in the center of Key West, only minimum 28 days stay, walk to shopping center, restaurant and water sports.1/1 in the first floor with a large gourmet kitchen, a very large master bedroom with a large balcony overlooking the pool, 2 bedrooms in the other side sharing a bathroom.Very ...

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Property Type

Key West House

"Loved everything about this place !!!"
Reviewed February 2, 2020

Wonderful place !! Our family had the best Christmas in Summerland keys! Loved all the wall art so we purchased the same ones

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LUXURY HOME WITH DOCK, POOL, HOT TUB, AND ELEVATOR

3 BR | 3 BA | Sleeps 8 | Quick View

5

Distance to beach: 1 miles to Coco Plum & Sombrero Beach

$405

avg/night

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Key Amenities

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

About this property

This new gated Marathon home is 2 levels with an elevator. 3 Bedroom / 3 Bathroom , Sleeps 8 people, with all the comforts of home. This home offers nothing but the best in home furnishings and security. Panoramic water views from private decks off the living room and master bedroom. Master / King bed; ...

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Property Type

Marathon House

"EVERYTHING you need for a relaxing vacation!"
Reviewed February 2, 2020

Larry’s place has everything you need and so much more! We did fish right from the pier in front of the house, had fun with a rented boat, went for an amazing snorkelling trip... Also many relaxing days ...

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Best location in the Keys, 150-foot dock, coconut palms on the beautiful beach.

$458

avg/night

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Key Amenities

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

About this property

The charming, oceanfront house directly on the beach. Most beautiful spot in the Keys! Very private, like being on your own tropical island. Coconut palms, 150-foot dock, mooring whips for a flats boat. Turtle nesting beach, Key deer, many tropical birds, and great fishing.  Inshore: tarpon, bonefish, ...

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Property Type

Big Pine Key House

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Bougainvillea Villa Key West-monthly rental on water with private pool & dock

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 4 miles to Smathers

$280

avg/night

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Key Amenities

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

About this property

COVID-19 UPDATE: Key West and Monroe County are opening to visitors June 1! Restuarants will be open at 50% capacity and bars that do not serve food will remain closed. MONTHLY RENTALS ONLY We purchased Bougainvillea Villa in late 2014 as our future retirement home. The villa was built in the early ...

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Property Type

Key West House

"Beautiful Bougainvillea Villa"
Reviewed February 27, 2018

Nothing is missing from this very clean and very well organized beautiful home situated on a wide lagoon. For us, the highlight is the superb view of the wide lagoon from the window wall across the entire ...

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Direct Oceanfront Views at Sea Gulls

2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 4 miles to Harry Harris Park

$243

avg/night

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Key Amenities

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

About this property

Sea Gulls 511 is one of the nicest condos in the Islamorada area. It has been completely rebuilt following Hurricane Irma so everything about it is new, upscale, and extremely clean.The living area is open plan with a large island, full kitchen, and most importantly, a fabulous direct ocean view ...

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Property Type

Tavernier Condo

"Beautiful oceanfront view!"
Reviewed July 2, 2019

The location of the condo was very nice, there are plenty of restaurants and attractions to go to. If you are looking for a relaxing vacation this is the place to stay. We will be back in the future! Love ...

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Beacon Reef Condominium 205

2 BR | 2 BA | Sleeps 4 | Quick View

$167

avg/night

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Key Amenities

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

About this property

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

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Property Type

Islamorada Apartment

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Luxury Direct Oceanfront Condo Seasonal Rental Available. Monthly Only.

$319

avg/night

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Key Amenities

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

About this property

Monte Christo Condominium, a Premier 38 unit oceanfront property in beautiful Key Colony Beach. Ground floor, corner, direct oceanfront unit. Gourmet kitchen. Ocean views from kitchen, dining and living areas, beautiful ocean sunrises from your master bedroom. This condo has been totally renovated to ...

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Property Type

Key Colony Beach Condo

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MA923 101st St Ocean Street Marathon, FL 33050

6 BR | 6 BA | Sleeps 14 | Quick View

Distance to beach: 5 miles to Sombrero

$714

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

The Pelican's Nest………New six bedroom, six bath completely remodeled in 2018. This is truly PARADISE. There is 150' of concrete step down dockage, with instant ocean access. The house is one lot in from the ocean, views are outstanding, while affording protected dockage. Fish right ...

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Property Type

Marathon House

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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

$380

avg/night

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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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Beautiful 3BD 3BA Villa in the Exclusive Flamingo Island

3 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 3 miles to Sombrero Beach

$483

avg/night

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Key Amenities

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

About this property

Welcome to Villa Nena!Stay in a beautiful villa in the exclusive Flamingo Island in Marathon, FL, located on a lagoon close to the famous Sombrero Beach and many well-known local restaurants. With the home just 10 min from the ocean by boat, you can enjoy the Florida Key's world class fishing, snorkeling, ...

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Property Type

Marathon House

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Key West Old Town Sanctuary- Huge Private Pool- Quiet Lane- Monthly Rental

$271

avg/night

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Key Amenities

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

About this property

Looking to ​ Relax Renew Recharge? We got you. Your own Key West Sanctuary awaits! Escape to a classic Conch family home perfectly tucked away for privacy yet, only 5 Blocks from famous Duval Street. The best of both worlds! Morning yoga class on the deck, late night dip in the pool, and sunset ...

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Property Type

Key West House

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Nov & Dec Discount/Waterfront/Open Gulf Access/Dock/Pool/Spa/Wraparound Deck

3 BR | 2 BA | Sleeps 8 | Quick View

2
LAST MINUTE DEAL 10/31 - 12/7: November and December weekly rate discount $2230 total Oct 31-Dec 19, excluding holiday weeks.

$294

avg/night

View Details

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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DEAL
Hogfish Hideout - New Swimming Pool

$223

avg/night

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Key Amenities

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

About this property

Welcome to the cleanest blue water flow-thru canal in the Keys! This comfortable home is clean and conveniently located at MM 24.5 on Summerland Key, near the beginning of a deep blue water canal.This elevated CBS home has concrete floors covered in ceramic tile and carpet in the bedrooms. The ...

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Property Type

Summerland Key House

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Oasis in the Keys

3 BR | 2.5 BA | Sleeps 8 | Quick View

$393

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront

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. A large patio provides ample seating and covered alfresco dining, while a private yard offers instant access to the clear blue waters.Use the ...

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Property Type

Marathon House

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Islamorada Beachfront Apartment - Great Sunsets! Private Beach!

$179

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Oceanfront
  • Rentals by Owner

About this property

The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach ...

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Property Type

Islamorada Apartment

"Excellent getaway, beautiful setting your own beach, The evenings were the best."
Reviewed September 22, 2020

This was the perfect getaway spot for us. The apartment has everything you need and more. The owners were excellent and very accommodating. Nothing like having your own private beach to enjoy. We even ...

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Chic marina front villa!

2 BR | 2.5 BA | Sleeps 6 | Quick View

$345

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

VRE 19-33 Mariner`s Club Resort ~ Out your door and onto your boat! ~ FREE Wifi! Instantly feel the warm island spirit greet you when you enter this elegant ground floor villa in Mariner's Club Marina and Residences.An expansive view of the blue harbor is accented perfectly by plush, leather sectional ...

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Property Type

Key Largo Condo

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

$345

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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Large Oceanfront condo with stunning views of Atlantic Ocean

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.3 miles to Founders Park

$217

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront

About this property

Spacious 3 bedroom/ 2 bathroom condo on the Atlantic ocean with large screened patio on second floor; private underground parking, oceanfront pool and beach, tennis, pickle ball, protected marina with boat ramp, Elevators for easy access to beautiful ocean views. Close to restaurants, shopping, hiking ...

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Property Type

Islamorada Condo

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4Bed/3bath, Tiki Hut, Canal,Cabana Club &INCH BEACH

4 BR | 3 BA | Sleeps 8 | Quick View

2

Distance to beach: 0.9 miles to Cabana Club

$275

avg/night

View Details

Key Amenities

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

About this property

ENJOY OUR HOME with 5 STAR REVIEWS & TIKI HUT, Open Water Access 5 minutes NEW WHITE kitchen with QUARTZ COUNTERTOPS, NEW STAINLESS STEEL APPLIANCES (photos coming soon),TOTALLY REDONE AFTER HURRICANE IRMAPerfect home for a Family Gathering, or Extended Family Get Together, or Families ...

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Property Type

Key Colony Beach House

"Great and comfortable stay!"
Reviewed December 30, 2019

The home was well equipped and comfortable! Homeowner very easy to work with and eager to help in any way possible to make stay perfect!

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Keys House with Deep Water Dock

3 BR | 3 BA | Sleeps 8 | Quick View

1

$617

avg/night

View Details

Key Amenities

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

About this property

Gorgeous three story home completely remodeled and refurnished using tropical island type colors and décor. Located on one of the only true deep water canals in Islamorada, this house is only a few lots in from Snake Creek with great views on the second and third floors.Just a quick review ...

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Property Type

Islamorada House

"Amazing location, super clean and spacious house, huge pool"
Reviewed October 15, 2019

We stayed here with our family and it was an excellent trip. The dock was huge and the canal is really deep. We brought a 30 foot center console boat and caught a lot of fish. The owner Tony was really ...

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Truman Annex, Large Outdoors Beautiful Spacious 1st Flr, 2BR KING/twins, Pool

$301

avg/night

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Key Amenities

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

About this property

Hello out there: KEY WEST IS OPEN! TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! Large front yard and porch to watch Key West pass by. Beautiful and spacious in/out doors. Our fantastic cleaner has been with us for years. We are following CDC guidelines for ...

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Property Type

Key West Condo

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Waterfront Hideaway: Quiet Locals Experience with Dockage!. Waterfront Hideaway

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 3 miles to Sombrero Beach

$184

avg/night

View Details

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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If Paradise had an address...THIS would be it!

$450

avg/night

View Details

Key Amenities

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

About this property

VRE 19-31 Your only regret will be your stay is not longer... Sleeps 8 ~ Mariners Club Resort and Marina is the one of the finest condominium properties in all of The Florida Keys. A gated, oceanfront community with deep-water marina and direct ocean access for world-class diving and fishing adventure ...

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Property Type

Key Largo Condo

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Conch Cottage Key West's only real beach house

$414

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island.Enjoy full use of direct TV channels, free current video library ...

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Property Type

Key West House

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Toes in the Water

4 BR | 3 BA | Sleeps 10 | Quick View

$409

avg/night

View Details

Key Amenities

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

About this property

"Toes in the Water" ~ Rent one side or both! It is a gorgeous brand new beautifully decorated 4 bedroom 3 bath canal front Villa (pull out couch)! With a private dock that can accommodate a boat up to 40', private pool, plenty of parking for cars and boat trailer and a two minute drive to the ...

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Property Type

Marathon Villa

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Key Colony Vacation Rental by Owner

$150

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

"Capt Tadds place key Coloney"
Reviewed March 5, 2020

PLACE WAS QUIET AND HAD EVERYTHING YOU NEED FOR VACATION. OWNERS WERE EVERY NICE. Location Is good. Comes with a key banana cub pass for the time of your stay. The night we arrived was a band at sunset ...

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BPS15- Atlantic Seaclusion

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 17 miles to Bahia Honda State Park

$250

avg/night

View Details

Key Amenities

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

About this property

Beautiful 3 bedroom 2 bath spacious Caribbean-style waterfront home in Sugarloaf Shores. Complete privacy w/lush landscaped grounds and sparkling pool. One property in from open waters. Concret dock THIS IS A 28 DAY RENTAL -Rent $7500.00 -Security Deposit $1000.00 -Cleaning $300.00 -No Pets - Non refundable ...

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Property Type

Sugarloaf Key House

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Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks Kayaks

3 BR | 2 BA | Sleeps 6 | Quick View

6
Owner special: Last minute cancellation , available October 22 to November 20, anytime in between .

Distance to beach: 0.5 miles to White Marlin Beach

$512

avg/night

View Details

Key Amenities

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

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6Villa Marlin , 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. It has three bedrooms, two bath, private home totally renovated and remodeled, new furniture ...

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Property Type

Islamorada House

"Best vacation ever!"
Reviewed July 3, 2019

We stayed at Villa Marlin for 2 weeks this June and it was wonderful! The house is equipped with everything you could possibly need for the perfect vacation. The ice machine and bait freezer were a real ...

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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

$261

avg/night

View Details

Key Amenities

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

About this property

We have relaxed our cancellation policy for the remainder of 2020. We will offer a full refund up to 30 days prior to the Check-In date.This upscale home has been meticulously renovated with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and beautifully ...

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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

1

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

$380

avg/night

View Details

Key Amenities

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

About this property

We have relaxed our cancellation policy for the remainder of 2020. We will offer a full refund up to 30 days prior to the Check-In date.Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool ...

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Property Type

Key West House

"Great place to stay near everything."
Reviewed October 31, 2019

Beautiful condo in a great part of town. It was exactly as advertised. Wonderful. We visited the fort, beaches, pool, and numerous restaurants, bars, and shops. It was Fantasy Fest week. We ate at Bagtell’s, ...

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Waterfront Bungalow: Bring Your Boat on Vacation!. Waterfront Bungalow

2 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 3 miles to Sombrero Beach

$249

avg/night

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Key Amenities

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

About this property

Adorable half duplex with a bohemian island feel!This house is a 2 bedroom 1 bathroom, canalfront half duplex. There's a screened in porch so you can relax in comfort on the water. There is 24' of dock space. There's a BBQ grill, Cable TV, WIFI, washer/dryer, and all the amenities of home. The house ...

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Property Type

Marathon House

"Fabulous Place!"
Reviewed February 21, 2020

I can’t say enough good things about Waterfront Bungalow! We absolutely loved it! It was beautifully decorated with a bohemian vibe, perfect for the Keys! It is a great location within walking distance ...

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Hidden Cottage

3 BR | 3 BA | Sleeps 6 | Quick View

$433

avg/night

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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

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Summer Breeze (Family Escape) $3200 / WK

Key Amenities

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

About this property

The Summer Breeze is a beautiful family getaway on the waters edge. This oasis features a brand new in-ground salt water pool just feet away from the breath taking view of the turquoise waters of the Atlantic. Inside this newly renovated beach themed escape features an open kitchen and family room concept, ...

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Property Type

Marathon House

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Dockside Retreat -Canal Front Villa with a Tiki Hut, Kayaks, Bikes, Pool, Beach!

$413

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! Warm and inviting coastal decor, this 4/3 villa is the perfect vacation home! This beautifully decorated Villa is truly a relaxing retreat and a vacation home that offers you everything you need for a fun filled Keys vacation, including an oceanfront ...

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Property Type

Marathon House

"Awesome house!!!"
Reviewed January 27, 2020

We recently stayed in the dockside retreat and loved it. We traveled to Marathon with my wife, kids, and mother in law and all thoroughly enjoyed our stay. The house was clean, new, and had everything we ...

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MA945 334 Calzada de Bougainville Marathon, FL 33050

$543

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

The view over the lagoon will take your breath away. Lovely Sombrero Beach neighborhood, just a short walk to the beach (less than 1/2 mile). Very quiet residential area. Large lot with ample of parking for all your needs. Deep water 40' dock also has a kayak and jet ski dock. Fish cleaning table, fish ...

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Property Type

Marathon House

"Great property and location"
Reviewed July 17, 2020

We loved everything about this place. The home, the view, and the location. Sombrero beach is right around the corner and Publix is right off Sombrero Rd. We would definitely visit this location again.

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'A little Piece of Paradise" Islamorada, Fl. On the water! 3/2, 90 Ft of dock

$200

avg/night

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Key Amenities

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

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!'' Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. There is a 1/1 guest suite attached which does have its own seperate and private access with full kitchen and bath. Entire house has been remodeled, fully furnished, with a 90 ft Dock. Bring ...

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Property Type

Islamorada House

"Florida keys"
Reviewed October 10, 2020

Heaven on Earth , Can't wait to return . Annual Birthday trip with family and friends . Relaxing , fishing , feasting and enjoying good company in a beautiful location . Highly recommend

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Blackbeard Hideaway

2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 9 miles to Bahia Honda

$119

avg/night

View Details

Key Amenities

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

About this property

Enjoy the Florida Keys in this beautiful canal front two bedroom two bath house in a beautiful area on Little Torch Key. The house features a master bedroom with a king size bed, flat screen TV, and the second bedroom also has a king size bed. A well designed and fully equipped kitchen with everything ...

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Property Type

Little Torch Key House

"A month in Paradise."
Reviewed August 2, 2019

This was our first time staying on Little Torch Key and our first month long vacation. Blackbeard Hideaway and Jolly Roger Estates in general are now my favorite place in the Keys. Protected docking, ...

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Elegant ~ Stylish ~ Well-Designed

$354

avg/night

View Details

Key Amenities

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

About this property

VRE 19-28 FREE Internet! Open water view! Ahh...you are here!  Villa 124 at Mariners Club is a two bedroom, two and one-half bath luxury villa with stunning harbor and ocean view!  A smart floor plan features a spacious open living space. A split bedroom plan each with king beds affords ...

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Property Type

Key Largo Condo

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Take in the oceanview from your patios in this oceanfront 3 bedroom townhouse!

$426

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

VRE 19- 48 3-bed, 3-bath tri-level townhouse with pool and oceanview! Sleeps 6 in beds, maximum occupancy 8 ~ Welcome to this spacious, oceanfront 3-bedroom, 3-bath townhouse ideally located overlooking the center of resort’s spectacular oasis pool. Instantly feel relaxed looking at the clear blue ...

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Property Type

Key Largo Condo

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Waterfront Paradise on Canal W/New Pool

$355

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

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

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Property Type

Islamorada House

"Waterfront Paradise"
Reviewed July 26, 2020

This was a terrific location and home. The house and amenities were excellent. The backyard was the standout for our group with the pool, dock and Tiki area....this felt like a true resort get away. The ...

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Florida Keys Vacation Rentals