Florida Keys Vacation Rentals

(495 rentals)
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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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Key West House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
4 reviews
owner special
Owner special: Spring Booking Special- Book by 12/31 for April, May or June 2025 and get a 30% discount!

$829

avg/night

$829
avg per night
Owner special:
Spring Booking Special- Book by 12/31 for April, May or June 2025 and get a 30% discount!

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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 Condo
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
owner special
Owner special: Available weekly or monthly from January 1, 2025 due to cancellation

$496

avg/night

$496
avg per night
Owner special:
Available weekly or monthly from January 1, 2025 due to cancellation

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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This Condo comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks.

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Property Type

Islamorada Condo

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Islamorada House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
6 reviews
last minute deal
LAST MINUTE DEAL 12/9 - 12/23: Holiday Special - Book before December 25th, 2024 and save an additional 10% off for Jan, Feb or Mar

Distance to beach: 2 miles to Founders Park

Offer for: Dec 9 - Dec 23:
Holiday Special - Book before December 25th, 2024 and save an additional 10% off for Jan, Feb or Mar

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Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to your dream getaway in Islamorada! This 3-bedroom, 2.5-bath paradise boasts a gourmet kitchen with a Viking gas stove, a spacious dining area, and Internet-ready TVs for game days or movie nights.On the first floor, you will find two bedrooms, a full bathroom and a large entertainment area ...

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Property Type

Islamorada House

Featured review

"Awesome House & Canal"

We had a wonderful time here. The location is perfect. Close to restaurants, shops, and attractions. We spent a lot of time floating and frolicking in the canal. The house was spotless. The kitchen was ...

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DEAL
Key Colony Beach House
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 0.5 miles to Key Colony Cabana Club Beach

$570

avg/night

$570
avg per night
View Details

Key Amenities

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

About this property

Beautiful 2-story half duplex home on wide canal with boat slip. Sleeps 10 comfortably. 4 bedrooms, bathrooms and lower-level family room with mini kitchen make this a great place for multiple families to have private space or gather together.Plenty of parking for boat trailer and multiple vehicles, ...

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Property Type

Key Colony Beach House

Featured review

"Plenty of room and a great location!"

Rare find of 4 full baths and 4 real bedrooms (not a daybed stuck in a sunroom like some rentals market as a bedroom). House comes with everything you need - beach towels, coffee maker, toaster, blender, ...

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Marathon House
4 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 2 bathrooms
12 reviews

Distance to beach: 3 miles to Sombrero

$420

avg/night

$420
avg per night
View Details

Key Amenities

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

About this property

Manatee Cove-4BR/2BA, Pool/Spa, Tiki, Quick Atlantic access!Escape to the Florida Keys ~ Gorgeous 4BR/2BA Home on the Atlantic side of the canal in Marathon. Our home offers the best pool in our area; who can say no to a hot tub, pool, and bar stools in one? Swim right up to the Tiki and enjoy the ...

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Property Type

Marathon House

Featured review

"Paradise"

My family and I had a wonderful week here. The owner and property manager were both a pleasure to work with. Our favorite amenity was the pool and hot tub. We had plenty of space and all of the beds were ...

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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

$159

avg/night

$159
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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Marathon House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
8 reviews

$848

avg/night

$848
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Sailfish Villa, unit #6, is a brand new gorgeous, professionally decorated 5 bedroom 4 bath Villa with open water views on Vaca Cut! Enjoy sunrise and sunset colors and direct ocean and Gulf access! It has a private pool and boat slip for a boat up to 35' including motors. There is no additional ...

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Property Type

Marathon House

Featured review

"Grateful"

I have been coming to marathon with family for many years and have had many rentals.. Meredith I have to say is the best.. she worked with me with every question and plans that I had . Definitely would ...

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Marathon House | On the beach
6 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5 bathrooms
4 reviews

Distance to beach: 0.1 miles to Sombrero Beach

$1436

avg/night

$1,436
avg per night
View Details

Key Amenities

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

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

Featured review

"The house was perfect for our fishing trip."

The house was very clean, and location could not be better. The house was more amazing than the pictures showed. The outside tiki hut, (2) barbeque grills and pool made a perfect end to a day of fishing. ...

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

Distance to beach: 0.5 miles to White Marlin Beach

$705

avg/night

$705
avg per night
View Details

Key Amenities

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

About this property

Bring your boat and Jet SkisNestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. New heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, double jet ski lift, and two floors facing ...

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Property Type

Islamorada House

Featured review

"Fabulous location, off the beaten path, clean, owner available for questions and very responsive."

We stayed in this home for a month, the location is amazing if you love to paddle board, kayak and discover the many mangrove islands that are a five minute paddle from your dock. The outside area has ...

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

$210

avg/night

$210
avg per night
View Details

Key Amenities

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

About this property

This condo is located in one of Islamorada's most prestigious condo complexes.PROPERTY NAME: Beacon Reef #414 83201 Old Highway, Islamorada, FloridaLOCATION: Ocean side CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed MILE MARKER: 83.2DETAILS: ...

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Property Type

Islamorada Condo

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

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

$449

avg/night

$449
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

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Islamorada House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

$300

avg/night

$300
avg per night
View Details

Key Amenities

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

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

Featured review

"A rental that exceeded expectation"

A well maintained home in a perfect quiet setting. The owner Patrick was outstanding to work with and made sure that all was in order. He is an excellent communicator. Welcome bottles of wine greeted us. ...

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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

$183

avg/night

$183
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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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$195

avg/night

$195
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

3 Beds/2 bath townhouse in Islamorada, Florida Keys. Ground Floor features a full kitchen, full bath, living room with large tv, dining room with views of the tennis court, outdoor patio with BBQ and additional dining table. Second Floor features a large full bath, 1 king size bed, 1 queen size bed, 2 ...

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Property Type

Islamorada Condo

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

$571

avg/night

$571
avg per night
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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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Marathon House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
3 reviews

$1714

avg/night

$1,714
avg per night
View Details

Key Amenities

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

About this property

Located on the Highly sought after Sombrero Beach area of Marathon, which is the beginning of the lower keys just 50 min from Key West is our Florida Keys Tropical Paradise . Less than a third of a mile to the Sombrero Beach and the Sombrero Beach Park, With a deep water concrete dock with ocean access ...

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Property Type

Marathon House

Featured review

"Great house and location"

Highly recommend this home. My family of 5 just spent the week there and had a fabulous time. It had everything we needed. It was close to some amazing restaurants. Publix was around the corner. The beach ...

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

$839

avg/night

$839
avg per night
View Details

Key Amenities

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

About this property

2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden 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, ...

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Property Type

Key West House

Featured review

"A little slice of heaven on earth"

The location is perfect - about 3 blocks from Duval, and 3 blocks from Truman, and a short bike ride to Ft. Zachary beach. We did not have a car, and did two Uber runs for groceries at Publix, then used ...

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

$635

avg/night

$635
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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Key Largo Apartment
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
owner special
Owner special: December Special. Holiday's in the beautiful Florida Keys. Contact us for discounted price.

Distance to beach: 13 miles to Harry Harris Beach and Park, 50 E Beach Rd,

$93

avg/night

$93
avg per night
Owner special:
December Special. Holiday's in the beautiful Florida Keys. Contact us for discounted price.

View Details

Key Amenities

  • Air conditioning
  • Rentals by owner

About this property

Fully Renovated in 2024!! Cozy beautiful 1 BR 1 BTH ground floor apartment with dedicated off-street parking. Enjoy amazing sunsets from our Waterfront Homeowners Park less then 2 blocks away.Key Largo is a great place to spend some time with amazing restaurants, bars and local attractions. Grocery ...

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Property Type

Key Largo Apartment

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Key Colony Beach Villa | On the beach
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 1 miles to In the Key Colony Beach walking distance

$1161

avg/night

$1,161
avg per night
View Details

Key Amenities

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

About this property

Hey there, fishing enthusiasts and families!Looking for the perfect Florida Keys getaway? Look no further! My beautiful waterfront home in Key Colony Beach is your dream vacation spot.Imagine this: You wake up to stunning sunrises over the open water, have coffee on the wrap-around porch, and ...

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Property Type

Key Colony Beach Villa

Featured review

"Group Vacation"

Stayed with a group of friends from around the country. The house was very clean and well provisioned Kitchen, bedrooms, bathrooms, outdoor cooking area. Met the host and hostess, who were very pleasant. ...

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Marathon House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms
18 reviews

$452

avg/night

$452
avg per night
View Details

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

"Wonderful experience!"

Everything was just as we had hoped for. Lynn and Freida always make you feel right at home-- only better! Thank you again for your hospitality and the sharing of your beautiful home!

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$428

avg/night

$428
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Mother Ocean!This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room ...

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Property Type

Islamorada Condo

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

$507

avg/night

$507
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

"SOMBRERO HEAVEN" is a canal front 4 bedroom 3 bath attached Villa with neighborhood ocean front beach just down the street! It has a private pool that can be heated or chilled (for a fee), private dock (up to 35' boat), fish cleaning station, bait freezer and 4 new bikes! Additionally, ...

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Property Type

Marathon Villa

Featured review

"Everything you could want in a vaca rental"

Meredith is prompt and helpful. Everything you could want at the beach or for your boat is provided. This is a big plus if flying in. Hope to return here. Highly recommend!

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

$544

avg/night

$544
avg per night
View Details

Key Amenities

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

About this property

The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is just ...

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Property Type

Key West House

Featured review

"WonderfUll"

The heated pool, tiki bar and view of the ocean was just beautiful as "out of a storybook. The eggs and a home made lime pie from Carol (owner) was a nice surprise. The house was plenty big enough to house ...

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Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$200

avg/night

$200
avg per night
View Details

Key Amenities

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

About this property

Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the 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 Condo

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Summerland Key House | On the beach
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
View Details

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

$120

avg/night

$120
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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Ramrod Key House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
5 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

"Paradise in the Keys!"

Beautiful home with absolutely gorgeous view. All the amenities made for a wonderful stay. Fred & Marilyn were the best to work with. Love this home.

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Islamorada House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
16 reviews

$367

avg/night

$367
avg per night
View Details

Key Amenities

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

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 2022 Remolded bathrooms, 2021 NEW POOL** Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 8. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath. Entire house ...

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Property Type

Islamorada House

Featured review

"The BEST of the BEST in every way!"

By far and away, this was the best rental property we have ever stayed! We have been visiting Islamorada for nearly 20 years and have stayed almost everywhere you can imagine, and we have now struck gold ...

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Islamorada House | On the beach
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 DockVilla 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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Marathon House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
11 reviews

$810

avg/night

$810
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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Islamorada House
4 BR | 2 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 2 bathrooms
4 reviews

$257

avg/night

$257
avg per night
View Details

Key Amenities

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

About this property

ALERT: BRAND NEW POOL JUST COMPLETED AND INSTALLED....DOWNSTAIRS IS AVAILABLE TO RENT BUT IS NOT INCLUDED IN THE PRICE feel free to ask about downstairs pricing and availability. Downstairs is an additional 3br and 2ba so the upstairs and downstairs would be a total of 7br & 4ba....THIS LISTING ...

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Property Type

Islamorada House

Featured review

"A month in heaven"

My wife and I spent the month of Dec. 2022 at this property in Islamorada (HEAVEN) in the Keys. The property has a pool, a canal and a boat dock that can handle any boat.Let me start of saying that ...

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Marathon House
4 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4.5 bathrooms
21 reviews

Distance to beach: 4 miles to Sombrero Beach

$847

avg/night

$847
avg 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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Islamorada House | On the beach
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$946

avg/night

$946
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Introducing the "Bonefish House" at Tarpon Point!This opulent, luxury, home is equipped to accommodate eight adults with 4 bedrooms & 4 full bathrooms. The open living space offers easy entertaining and direct panoramic views of the community pool and Atlantic Ocean. The well-appointed ...

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Property Type

Islamorada House

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

Distance to beach: 2 miles to Founders Park

$697

avg/night

$697
avg per night
View Details

Key Amenities

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

About this property

This tropical waterfront beauty has it all...heated pool, spa, dock and custom elevator. Beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal with direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one of several patios ...

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Property Type

Islamorada House

Featured review

"You found it"

If you’re looking for a well kept beautiful home, right on the water positioned right between the Gulf and Atlantic, great pool and hot tub YOU FOUND IT. Communication is great and owner is so helpful. ...

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Islamorada Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
6 reviews

$123

avg/night

$123
avg per night
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Key Amenities

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

About this property

Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2 ...

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Property Type

Islamorada Condo

Featured review

"Beautiful Oceanfront Condo"

Plantation by the Sea is an older condo complex that is beautifully maintained. The condo is located at MM 87.5 just off of U.S. 1 in the heart of Islamorada. Restaurants of various types can be found within ...

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

Distance to beach: 3 miles to Anne's Beach State Park

$314

avg/night

$314
avg per night
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Key Amenities

  • Air conditioning
  • WiFi

About this property

This 3-bedroom bayfront property is located on Lower Matecumbe in Islamorada. The view is spectacular with sunsets on the water most of the year. There is plenty of room for boat trailers, RVs and other toys inside the fence. There is covered parking for your vehicles and a seawall out front to tie your ...

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Property Type

Islamorada House

Featured review

"Lower Matecumbe"

All I can say is that this place never fails to impress! The views from every inch of the property are the best in all of the keys! Great communication with Rich and his office. Would recommend every ...

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Marathon House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
1 review
last minute deal
LAST MINUTE DEAL 12/11 - 1/22: Florida Keys Christmas Week $499 per night 12/20 to 12/27

$399

avg/night

$399
avg per night
Offer for: Dec 11 - Jan 22:
Florida Keys Christmas Week $499 per night 12/20 to 12/27

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Key Amenities

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

About this property

NEW TO MARKET AND AVAILABLE FOR LOBSTER MINI SEASON!!! This new construction has everything. This concrete house is waterfront with great views of Bonefish Bay. The 70 foot dock is built in 10-12 foot water. It is frequented by manatee, dolphin, and numerous mangrove snapper. The large heated pool ...

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Property Type

Marathon House

Featured review

"Excellent home"

You and your friends and family will love this paradise.. Stayed here 4 times already. Don't pass up the opportunity to see for yourself!

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

Distance to beach: 9 miles to Bahia Honda

$156

avg/night

$156
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

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

Featured review

"Beautiful Escape"

We enjoyed our stay in this extremely comfortable home. Beds were very comfortable and location was close to lots of restaurants and local attractions. Having a place for our boat was the best. We could ...

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Key West House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms

$627

avg/night

$627
avg per night
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Key Amenities

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

About this property

Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Dos ...

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Property Type

Key West House

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Islamorada Villa
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
14 reviews

Distance to beach: 5 miles to Anne's Beach

$325

avg/night

$325
avg per night
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Key Amenities

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

About this property

The "Nest" villa (one of 7 privately owned condo residences) sits on a 1 acre lot located on Islamorda's beautiful Florida Bay. Stunning water views and unforgettable sunsets are guarenteed. The property is filled with mature tropical landscaping along a tree lined private gravel driveway ...

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Property Type

Islamorada Villa

Featured review

"Amazing location, view, and super clean!"

My 18 yr old son and I stayed here at the end of September and it was a fantastic trip!We have been going to the keys for 14 years several times a year. This unit is the cleanest we have ever seen! ...

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Islamorada House | On the beach
6 BR | 7.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 7.5 bathrooms

Distance to beach: 1 feet to on property or at Founders Park

$373

avg/night

$373
avg per night
View Details

Key Amenities

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

About this property

Beautiful new home on Florida Bay with sandy beach, spacious pool, beautiful views, and sunsets every night. Three Private Suites are offered to accommodate up to 12 guests. Each suite can be rented individually or combined. I would be happy to discuss your needs and answer any questions you may have. ...

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Property Type

Islamorada House

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Key West Condo
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom
1 review

Distance to beach: 0.5 miles to South Beach

$297

avg/night

$297
avg per night
View Details

Key Amenities

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

About this property

This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * Pet Friendly for flat fee of $90 * King size bed * WiFi included * check-out cleaning is an additional fee of $70 * 2 wall AC units * flat screen TV * Shared gas grill ...

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Property Type

Key West Condo

Featured review

"Perfect Place to Stay"

This was our 3rd time staying in Pam's wonderful little cottage. My husband and I really love this place. Pam is awesome to work with, she always answers all my questions quickly. It was great being close ...

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

$264

avg/night

$264
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

This nicely appointed home is located in Key Haven subdivision of fine homes. It offers an expansive living room with upgraded kitchen and appliances. The kitchen is nicely stocked with plenty of room for multiple cooks. The house can accommodate up to six people with 3 bedrooms and 2 full bathrooms. ...

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Property Type

Key West House

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Key West House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$399

avg/night

$399
avg per night
View Details

Key Amenities

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

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

Featured review

"Great location!"

We loved this house at the end of a quiet lane. Huge pool! The location was perfect, walking was easy to so many places. Fully fenced and a small backyard made it perfect for our dog. And the shower ...

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Marathon House | On the beach
14 BR | 10 BA | Sleeps 30 | Quick View
Sleeps 30, 14 bedrooms, 10 bathrooms

Distance to beach: 100 yards to Sombrero Beach

$2464

avg/night

$2,464
avg per night
View Details

Key Amenities

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

About this property

Seaside Sandpiper is truly a unique property that can accommodate as few guests as you want and up to 30! Rent the 6 bedroom main house by itself or rent the entire 14 Bedroom Main house and Addition! Weddings, family reunions and business retreats are all possible at our home! Our pet friendly home ...

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Property Type

Marathon House

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Key Colony Beach House | On the beach
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* JAN 18-31 $1995WK BOOK CASAMARAZUL

Distance to beach: 0.3 miles to Exclusive Inch Beach

$417

avg/night

$417
avg per night
Owner special:
46 FOOT DOCK, PRIVATE POOL, WALK 2 CABANA BEACH CLUB *JAN SALE* JAN 18-31 $1995WK BOOK CASAMARAZUL

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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Key Largo Condo
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms
5 reviews

$281

avg/night

$281
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Look no further than this perfect place in the Keys for your next vacation! Our cozy condominium provides an ideal location to enjoy the best of the Florida Keys and has some of the best views in all of Key Largo!Located on the 5th floor, you are the top floor of the building with no one above to ...

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Property Type

Key Largo Condo

Featured review

"A Little Slice of Heaven"

We can’t say enough about staying at Moon Bay 507. Great location , attentive hosts, clean and comfy condo, great view, wonderful pool and waterfront. We’ve been there twice and hope to return soon.

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Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review
owner special
Owner special: 15% off Jan1 through Feb 4 2024. I rent from Saturday to Saturday so take 1 2 3 or 4 weeks Remodeled

$318

avg/night

$318
avg per night
Owner special:
15% off Jan1 through Feb 4 2024. I rent from Saturday to Saturday so take 1 2 3 or 4 weeks Remodeled

View Details

Key Amenities

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

About this property

We have owned and rented this property for 20 years and have been coming to Seagulls Condominiums for over 40 years. The condo bathrooms and bedrooms have just been updated and the entire building has just finished a major upgrading and painting. If my pics don't import from vrbo 49422, then you ...

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Property Type

Islamorada Condo

Featured review

"Outstanding view and amenities. Will return soon!"

Classic art deco style building which was fully remodeled both inside and out. The owners are very responsible and have been doing this a long time.

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