Florida Keys Vacation Rentals

(495 rentals)
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Key West Condo
1 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 2 bathrooms
3 reviews

$271

avg/night

$271
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the ...

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Property Type

Key West Condo

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Marathon House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
7 reviews

$537

avg/night

$537
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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 (1/2 the dock), 2 bikes, 2 kayaks, bait freezer, gas grill! The private dock can accommodate ...

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Property Type

Marathon House

Featured review

"Family reunion"

Excellent stay, everything in the house worked smoothly, nice big pool, kayaks at our disposal, Sombrero beach, groceries in just few minutes of drive. One ctisism: no garbage recycling option.

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Marathon Villa
4 BR | 3 BA | Sleeps 14 | Quick View
Sleeps 14, 4 bedrooms, 3 bathrooms

$700

avg/night

$700
avg per night
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Key Amenities

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

About this property

WELCOME TO THE KEYS! Mega tropical oasis with 2 HOUSES! No you are not dreaming. Yes there are 2 houses connected together totaling 5 beds, 3 full bathrooms, 2 outdoor showers , 2 six person Hottub’s and 2 kitchens. Along with kayaks, beach bikes, volley ball, bocci ball, fire pit, corn hole and ...

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Property Type

Marathon Villa

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Key West Villa
6 BR | 7 BA | Sleeps 16 | Quick View
Sleeps 16, 6 bedrooms, 7 bathrooms
3 reviews

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1791

avg/night

$1,791
avg per night
View Details

Key Amenities

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

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

Featured review

"Glenn dinner group get away"

We had 6 couples visiting key west for a week to celebrate milestone birthdays and get away. The houses were perfect for our group. Beautifully decorated,plenty of space for everyone to enjoy and not ...

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Cudjoe Key House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$235

avg/night

$235
avg per night
View Details

Key Amenities

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

About this property

Unit #179 - At the “Tree Top Paradise” we have spared no expense to make sure your vacation is not just a vacation but an experience of your life with a peak a boo view of the canal. This home is a fantastic 2 bedrooms (Queen beds) and a sleeper sofa and 2 baths. You have a large lovely screened ...

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Property Type

Cudjoe Key House

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Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$500

avg/night

$500
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is an extra large floor plan with a nice ocean view. This property features 2 queen beds in the master bedroom and a king in the guest bedroom. Full size washer/ dryer and 1 assigned private ...

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Property Type

Key West Condo

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Key West House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

$440

avg/night

$440
avg per night
View Details

Key Amenities

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

About this property

Down a very quite lane the house has one off street parking spot. If you are familiar with Key West you understand what a treat it is to have off street Parkin !Enter from gate through lush and colorful walk to front door of main house . Walking over the front porch is the typical Key West style outside ...

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Property Type

Key West House

Featured review

"A hidden gem in Key West!"

We loved our stay at Hidden Cottage! Located on a perfect bike loop with bike-lane to Duval (one way on Southard to Duval and one way on Fleming home)! Also very close to the boat docks. Hidden Cottage ...

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Key West House
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$378

avg/night

$378
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in ...

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Property Type

Key West House

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Key West Apartment
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom

$309

avg/night

$309
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view ...

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Property Type

Key West Apartment

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Little Torch Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 23 miles to Marathon

$185

avg/night

$185
avg per night
View Details

Key Amenities

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

About this property

Charming house on a canal with all amenities like home. Bring your own boat and park it on the dock for the duration of your vacation. Convenient located 25 miles before Key West. Nice restaurants and groceries shopping 10 minutes from the house Marathon is only 30 minutes away. A short boat ride ...

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Property Type

Little Torch Key House

Featured review

"Amazing vacation!"

This canal front home is close enough to everything to be convenient, yet far enough away from everything to be private and secluded. Easy access to the Atlantic and Gulf for boating, close to picnic ...

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Key Largo House
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
1 review

Distance to beach: 6 miles to John Pennekamp State Park

$158

avg/night

$158
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront

About this property

1 BR/1 Bath Rare Find! Lovely oceanfront home with large private boat basin. This ground-level house has two enclosed sleeping areas - a master bedroom with a king bed, and a private alcove providing sleeping space for up to 4, with 2 bunks and a full-sized bed (separated from the living room by an ...

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Property Type

Key Largo House

Featured review

"Mahalo ocean view"

We loved every minute of our vacation. The sunsets were magnificent. Fun meter is high with a unique blend of restaurants and tiki bars. So convenient having a boat slip. We will be back!

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Little Torch Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

$250

avg/night

$250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Beautiful water-front home on a flow-through canal. Minutes by boat to the Atlantic or Gulf for world-class fishing, diving, and other water sports. Twenty-five minutes by car to Key West or Marathon. Beautiful beaches at nearby Bahia Honda State Park. This home features 2 large bedrooms, 2 bathrooms, ...

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Property Type

Little Torch Key House

Featured review

"Family vacation"

This property is amazing. The house was very clean, well stocked with paper products and cleaning supplies. The owners checked in with me several times to make sure there were no issues which there was ...

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Marathon Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
7 reviews

$250

avg/night

$250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Small Pets OK, Beautiful and remodeled , 2 bedrooms, 2 bathrooms ideal getaway in Coco Plum Beach, the Florida Keys. Our reviews are excellent! Amazing amenities, that include waterfront swimming pool, boat dockage included for boat up to 35’, on-site boat ramp and fish cleaning station. Comes ...

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Property Type

Marathon Condo

Featured review

"Fun in Marathon"

Decided on this condo because it had a private boat ramp. When we arrived it was as advertised and much more. The unit was well done and very CLEAN. My wife is a designer by trade and she was impressed. ...

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Ramrod Key House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
6 reviews

$267

avg/night

$267
avg per night
View Details

Key Amenities

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

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

Featured review

"Wow! What a View!"

This 4 bedroom, 2 bath is more than a house, it feels like home! From the fully stocked kitchen to the various board games available, this house will keep you busy. You can also rest here as the nights ...

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Key West Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$517

avg/night

$517
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Come find your slice of paradise in this 2 bed 2 full bath newly renovated condo. This listing is perfect for those wanting to be close to the airport and near main attractions but away from the hustle and bustle of Old Town. Located in New Town and near Smathers Beach. This condo has a pool, hot tub, ...

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Property Type

Key West Condo

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Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
9 reviews

Distance to beach: 0.5 miles to White Marlin Beach

$643

avg/night

$643
avg per night
View Details

Key Amenities

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

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6 Pure High End Luxury with all the Bells and Whistles Boat Friendly Vacation Rental with Dock Villa 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. ...

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Property Type

Islamorada House

Featured review

"Perfect, quiet, and secluded"

This was a spectacular vacation! The house was clean and comfortable, and the location was quiet and the setting perfect. I could write a novel about the host and the house, but in a few words the host ...

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Islamorada House
2 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 2 bathrooms
2 reviews

$118

avg/night

$118
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Located at Mile Maker 87 Bayside. This gated condo complex offers a large heated pool, club house, Jacuzzi, two tennis court, large Bayside beach. This townhouse (sleeps 8) has just been totally renovated with beautiful tropical furniture, all new kitchen, small garden patio with hammock, living room ...

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Property Type

Islamorada House

Featured review

"Great vacation"

We have never stayed in the Florida Keys before so this was a new adventure that we will definitely do again. The weather was a perfect 80 degrees. Nothing but chill time. We would start the day in the ...

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Cudjoe Key House
5 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3 bathrooms
2 reviews

$745

avg/night

$745
avg per night
View Details

Key Amenities

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

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

Featured review

"Squillets & Manor Wedding"

We had a great time, we will definitely be back! Fun in the sun! Close to restaurants and grocery store.

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 100 feet to Front door

$220

avg/night

$220
avg per night
View Details

Key Amenities

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

About this property

MINIMUM STAY: 30 days Spacious and beautiful 2 bedroom/2 bath ocean front condo unit with unobstructed ocean views. BOAT SLIP is available upon request for up to a 46 foot boat, low tide draw is 30 inches. There is an additional fee for boat slip. Walk out your front door and go boating. You’ll ...

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Property Type

Islamorada Condo

Featured review

"Pure serenity"

So clean, so quiet, so beautiful! My wife and I loved our stay at Ocean Harbour. Looking forward to next year!

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Marathon House
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

$317

avg/night

$317
avg per night
View Details

Key Amenities

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

About this property

This charming oceanfront property is the perfect getaway for your next vacation. Located just steps away from the ocean, this cozy retreat features stunning views, modern amenities, and a spacious deck for outdoor relaxation. Enjoy the convenience of nearby shops, restaurants, and attractions. Book your ...

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Property Type

Marathon House

Featured review

"Oceanfront Property Marathon FL"

Newer, modern, comfortable, and well decorated oceanfront property. Had everything we needed and more. Beautiful views from the deck and very nice outside area. We appreciated that there were great ...

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Key West House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

$620

avg/night

$620
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6 This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is a nice ...

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Property Type

Key West House

Featured review

"Southern Charm with a boat slip!"

Our family had a wonderful time staying in this townhome style rental. We relaxed and enjoyed the views of the bay and marina from the back porch. The boat slip worked great for our rental boat. This ...

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Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$783

avg/night

$783
avg per night
View Details

Key Amenities

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

About this property

Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and travels of “Papa” Earnest Hemingway. This is a beautiful top floor two-bedroom ocean-view unit at 1800 Atlantic condos. It has pristine ocean-views from all rooms ...

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Property Type

Key West Condo

Featured review

"SIMPLY DIVINE"

BEST PLACE WE EVER STAYED AT. THERE WERE FOUR OF US. BEAUTIFUL LOCATION. SO COMFORTABLE. KIRK WAS SO HELPFUL TO HELP US GET SETTLED IN. ALL THE TREATS OF HOME. VIEW INCREDIBLE. WANTED OUR TIME THERE TO ...

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Islamorada Apartment
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
46 reviews

$175

avg/night

$175
avg per night
View Details

Key Amenities

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

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

Featured review

"Slice of Paradise"

We’ve been coming to the Keys for 20 years and this place takes the win. Jerry and Lisa are so friendly and make you feel very welcome and comfortable. The apartment has everything you need including ...

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Islamorada House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms
15 reviews

$789

avg/night

$789
avg per night
View Details

Key Amenities

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

About this property

There's a reason why we have ALL 5-star reviews! HeartofMorada is located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries that you will love! The home is just 3 years old and WELL apportioned with everything you'd need on vacation and ...

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Property Type

Islamorada House

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Marathon House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
6 reviews

$815

avg/night

$815
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Pineapple Tides, located at "The Tides at Vaca Cut" (Unit #8), is a new 5 bedroom 4 bath home with a private pool and boat slip! Perfectly situated on the water with stunning views, sunrise and sunset colors, and direct quick access to both the Atlantic Ocean and the Gulf of Mexico via Vaca ...

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Property Type

Marathon House

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Marathon Villa
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
7 reviews

$598

avg/night

$598
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Reel Life 2 has everything! 4 bedroom 3 bathrooms, canal front, private dock (boat up to 35'), large private pool, Tiki Hut with flat screen TV, large grill, 2 bikes, 2 paddle boards, 1 kayak and a natural landscape view across the canal! Plus, Sombrero Beach is just down the street (1.3 miles). ...

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Property Type

Marathon Villa

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Islamorada House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$1317

avg/night

$1,317
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Islamorada House

Featured review

"Beautiful stay"

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

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Marathon House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
7 reviews

$582

avg/night

$582
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

DOCKSIDE RETREAT is a 4 bedroom 3 bath canal front home that has a private pool, private dock, fish cleaning station, with a green light under the dock, two paddle boards, a kayak, four bikes, and a Tiki Hut for the ultimate Keys vacation! There are 4 parking spots for vehicles and one boat trailer (you ...

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Property Type

Marathon House

Featured review

"This rental home has everything!"

We loved our stay at Dockside Retreat! The house was decorated perfectly for a tropical vacation. We used the pool every day. There were pool noodles, kayaks, cruiser bikes etc. We used all of the fun toys. ...

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Islamorada House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
7 reviews

$814

avg/night

$814
avg per night
View Details

Key Amenities

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

About this property

‘The Beach House’ at Tarpon Point in Islamorada- DIRECT RENTAL WITH NO ADMIN OR CC FEES Do not be deceived by other units' lower "nightly rates"; we are the largest/most private unit and have the lowest total rental cost! Why pay more for less? ‘The Beach House’ ...

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Property Type

Islamorada House

Featured review

"Very peaceful and beautiful accommodations"

Impressive location. View from master bedroom is fantastic. House was clean, comfortable, well furnished and great layout. Area is easy to navigate and lots of great restaurants close bye. Green Turtle ...

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Key Colony Beach House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
13 reviews
owner special
Owner special: 46 FOOT DOCK PRIVATE POOL, WALK 2 CABANA BEACH CLUB *JAN SALE* 1/25--2/1 $1897WK BOOK CASAMARAZULCOM

Distance to beach: 0.3 miles to Exclusive Inch Beach

$409

avg/night

$409
avg per night
Owner special:
46 FOOT DOCK PRIVATE POOL, WALK 2 CABANA BEACH CLUB *JAN SALE* 1/25--2/1 $1897WK BOOK CASAMARAZULCOM

View Details

Key Amenities

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

About this property

Note!! ALL Reservations are accepted on a "Saturday to Saturday" check in/Check out basis. VACATION HOME IS LOCATED IN KEY COLONY BEACH just a 2-3 Minute Walk to the Private Members Only "CABANA BEACH CLUB" Welcome to our Casa Mar Azul III, an upscale and luxurious 3 Bedroom, ...

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Property Type

Key Colony Beach House

Featured review

"Excellent home"

This house is exactly as pictured. This was our second visit to this home and we will be back. Pool was clean and a nice plus. Location is a nice quiet neighborhood

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Marathon House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
5 reviews

$663

avg/night

$663
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Tingler Retreat is a 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 ...

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Property Type

Marathon House

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Key West Condo
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
1 review

Distance to beach: 0.8 miles to Fort Zachary Taylor State Park and Beach

$446

avg/night

$446
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Our condo has always received great reviews on cleanliness and the bright citrus pallet is welcoming, there are 2 bedrooms (1 King & 1 Queen), one bathroom with couples walk in shower, The small but ...

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Property Type

Key West Condo

Featured review

"Sister, friend- and hubby vacation"

Attitude Key West Attitude Key West Key West Here in Key West we believe it is out restful but fun place where everyone is welcome and treated like family. this condo was clean and wonderful. Type: ...

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Key West House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Fantastic Location in the heart of Old Town Key West. This beautiful 3 bedroom 3 bath property is the perfect place to stay to be in the heart of the buzz of Key West. The main level of the house features living room, dining room, kitchen and full bath on the first floor The Master suite & both guest ...

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Property Type

Key West House

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Key West Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$1864

avg/night

$1,864
avg per night
View Details

Key Amenities

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

About this property

Tom's Oceanfront Penthouse is a spectacular oceanfront unit features 3 bedrooms and 2 bathrooms in a prime location within the complex. It is conveniently situated near the elevator and offers secure covered parking in the garage for vehicles under 6 feet 4 inches in height. Spanning approximately ...

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Property Type

Key West Condo

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Marathon Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 0.1 miles to On site

$516

avg/night

$516
avg per night
View Details

Key Amenities

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

About this property

BEST SUNSETS in the Keys, Key Colony Point unit #15, Ocean Beach Front, 2 bedroom, 2 bath ensuite, newly remodeled Condo with new furniture. COMPLEX: KEY COLONY POINT UNIT #15 Perfect get away for a week or a month. BEACH is 30 feet from our balcony. 150 feet to pool with hot tub. Great fishing ...

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Property Type

Marathon Condo

Featured review

"Best ever"

Absolutely the best view and pool in Key Colony. Spacious and well appointed condo. Would repeat #15 Very quiet and relaxing without crowds and annoying children!

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Marathon House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

$543

avg/night

$543
avg per night
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Key Amenities

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

About this property

Welcome to our private stand-alone oceanfront home in a quiet, yet friendly gated community in Marathon, Florida! If you’re looking for a relaxing and low-energy getaway for your family, you’ve found the perfect place. Consider a 14-day stay and receive an 8% discount OR 28-day stay and ...

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Property Type

Marathon House

Featured review

"Great house with fabulous views!"

In summary, fabulous views! From the roof you get both the Atlantic and gulf. Unobstructed 180 degree gulf view. The house is great too. Everything you need to sleep comfortably, relax, cook. Space for ...

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Big Pine Key House
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Enjoy breathtaking views of ISLAND TIME PARADISE (our nickname) in Big Pine Key. Its our spacious 3 bedroom 2 bathroom ISLAND TIME PARADISE HOUSE that will accommodate a total of 8 people. You will see it as the perfect blend of tranquil beach living and modern convenience. This home is the ideal place ...

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Property Type

Big Pine Key House

Featured review

"Wonderful home"

Loved staying at this home! Very comfortable! Owners were great to work with and extremely easy to work with! Got our security deposit back within a good time frame! I have no complaints except for the ...

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Islamorada Townhome
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2.5 bathrooms

$271

avg/night

$271
avg per night
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Key Amenities

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

About this property

Breathtaking Waterfront 2/2.5 Townhouse In Desirable Futura Yacht Club. Lots of outdoor living space,great for entertaining and enjoying the magnificent unobstructed Bayviews and beautiful sunset! Futuravis a gated community with a large pool tennis courts, boat ramp,beach and boat/trailer storage,parking ...

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Property Type

Islamorada Townhome

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Cudjoe Key House
4 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 2 bathrooms
5 reviews

$415

avg/night

$415
avg per night
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Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

BOAT RENTAL: We offer to rent our personal boats to our guests, only. We own: Flats Boat - 17 ft Ranger with E Tech 75 Bay Boat - 24 ft Bay Scout with 225 HP Yamaha Open Fisherman - 29-ft Ocean Runner with twin 300 HP Verrado's These boats are set up with everything you need to fish the Keys, ...

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Property Type

Cudjoe Key House

Featured review

"Vacation 2024/2025"

Southern Sunset is an excellent place to stay! The hosts are very accommodating and were great to chat with and helped make our stay even better. The property is clean and well kept and has a fabulous outdoor ...

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Marathon House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms
19 reviews
last minute deal
LAST MINUTE DEAL 1/9 - 1/18: Jan 19th-26th and 26th- Feb 2nd. Last min cancellation. $400 a night, 7 night min, Sun-Sun rental.

$441

avg/night

$441
avg per night
Offer for: Jan 9 - Jan 18:
Jan 19th-26th and 26th- Feb 2nd. Last min cancellation. $400 a night, 7 night min, Sun-Sun rental.

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Key Amenities

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

About this property

We would love for you to come visit our renovated ground level Florida Keys home! We decided to call our home "TIGHT LINES", because my wife loves to fish. Our conch home consists of 3 bedrooms with king size beds with ensuite bathrooms. A half bath for guests. We have a 60 foot dock with ...

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Property Type

Marathon House

Featured review

"Perfect Family Vacation"

Best Thanksgiving Trip! The house was beautiful and all accommodations were perfect! The owners were very helpful. Thank you!

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DEAL
Marathon House
2 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1 bathroom

Distance to beach: 3 miles to Sombrero Beach

$280

avg/night

$280
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Waterfront Hideaway! Experience tranquil serenity in the heart of Marathon, Florida with this stunning canalfront half duplex. Imagine waking up each morning to the soothing sound of palm trees in the wind, while you bask in the warmth of the Florida sun on your very own screened-in porch ...

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Property Type

Marathon House

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Islamorada House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms

$1744

avg/night

$1,744
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This grand peninsula retreat is embraced by the Ocean and lush mangroves, offering privacy to the heated pool with its tiki bar, expansive sandy playgrounds and lounge areas. Nestled along the tranquil shores of Florida Bay, its array of indoor and outdoor living areas, dock with ocean-access canal, gazebo ...

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Property Type

Islamorada House

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Marathon House
4 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4.5 bathrooms
21 reviews
owner special
Owner special: Book 7+ days Feb 25 - Mar 12 for $100 discount per night

Distance to beach: 4 miles to Sombrero Beach

$839

avg/night

$839
avg per night
Owner special:
Book 7+ days Feb 25 - Mar 12 for $100 discount per night

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Key Amenities

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

About this property

New construction! This spacious and tropically decorated property includes 4 KING bedrooms, each with private ensuite bathrooms. There is an additional half bath for guest use, as well as commercial washer and dryer. State of the art kitchen with quartz counter tops and well appointed living area including ...

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Property Type

Marathon House

Featured review

"Perfect location and home for exploring the Keys."

This beautiful home was perfect for our family reunion. The 4 king bed en-suite bedrooms are spacious with super comfortable beds and bedding. The family room/kitchen/dining area is a wonderful space ...

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Summerland Key House
7 BR | 5.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 5.5 bathrooms
5 reviews

$750

avg/night

$750
avg per night
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Key Amenities

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

About this property

Minimum 28-day rental. NO, this is NOT available to rent for fewer than 28 nights. Please don't ask. Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property....two large cottages (each two-bedroom) and a main house overlooking the ...

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Property Type

Summerland Key House

Featured review

"Perfect Tropical Oasis"

This is an incredible find! If you’re interested in this property, do not hesitate! In almost 30 years of traveling at least 15 times to Florida, this is by far the nicest place we’ve stayed. Whether ...

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Tavernier Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
11 reviews

$300

avg/night

$300
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to your remodeled 2 - bedroom, 2 - bathroom vacation rental that has everything you need! The Master bedroom features a comfortable king size bed with a private bathroom that has a walk-in shower. The second bedroom has 2 twin beds and a connecting bathroom. The kitchen boasts beautiful granite ...

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Property Type

Tavernier Condo

Featured review

"2 week vacay"

Our trip was wonderful! The condo was clean and nicely decorated. We had plenty of room and the view was priceless!

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Marathon House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$470

avg/night

$470
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Ocean Oasis Escape to this newly built, stunning 4-bedroom, 3-bathroom vacation home nestled in the heart of Marathon, FL. Perfectly situated in Coco Plum and boasting a private pool and dock, this retreat offers everything you need for an unforgettable getaway in the Florida Keys. ••• ...

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Property Type

Marathon House

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Key West House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
4 reviews

$748

avg/night

$748
avg per night
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Key Amenities

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

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny ...

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Property Type

Key West House

Featured review

"Beautifully Appointed Historic Home in Old Town"

I really can't rave enough about this home and the hospitality of the owners. The house is a beautiful historic home in old town that has been lovingly restored. The outdoor living space and the open to ...

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Islamorada House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$633

avg/night

$633
avg per night
View Details

Key Amenities

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

About this property

Welcome to your private slice of paradise in the heart of the Indian Waterways! This newly constructed Coastal Contemporary Caribbean-style home, with 165 feet of waterfront, invites you to experience the ultimate blend of luxury and tranquility. Unwind in Style: From the moment you step into the ...

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Property Type

Islamorada House

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Marathon House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
11 reviews

$762

avg/night

$762
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Blue Turtle Villa at The Tides of Vaca Cut (Unit #4), is a brand new 5 bedroom 4 bath home with a private pool, boat slip, all the toys for the perfect vacation ~ paddle boards, kayak, giant Jenga, giant connect four, ping pong and more! Perfectly situated on the water with stunning views, sunrise and ...

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Property Type

Marathon House

Featured review

"Beautiful vacation rental"

The home is absolutely beautiful and in a great location, beautiful views and has all the amenities needed for a great family vacation!

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Marathon Villa
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
2 reviews

$574

avg/night

$574
avg per night
View Details

Key Amenities

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

About this property

MARATHON ANGLER'S RETREAT in Marathon is a brand new property with every modern convenience and warm coastal decor! Located right on a canal (just 15-20 minutes from open water) it has its own private dock (can accommodate up to a 35' boat on a 32' dock), fish cleaning station, private ...

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Property Type

Marathon Villa

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