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Marathon Vacation Rentals with Private Pool

(87 rentals)
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

4BR 4.5BA Home w/ Fantastic Outdoor Entertainment Area, Outdoor Bar and Private Heated Pool!Casa Del Mar This stunning vacation rental features 4 spacious bedrooms, each with en-suite baths, including two master suites with king-sized beds and patio access. The open great room boasts a chef's...

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$784
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your perfect tropical getaway! This stunning, completely remodeled half duplex in Key Colony Beach offers a blend of modern luxury and coastal charm. From top to bottom, no detail has been overlooked in creating this immaculate vacation retreat.Relax and unwind in the spacious living areas...

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$393
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms
3 reviews

Key Amenities

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

About this property

Welcome to Tropical Sunsets, your tropical oasis in the heart of Marathon, Florida! This stunning 4-bedroom, 3-bathroom home offers a serene escape with breathtaking Gulf views and a perfect location for relaxation and adventure.*Saturday-to-Saturday Rentals OnlyProperty Overview: Prime Location: Tropical...

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$659
avg per night
Marathon House
Sleeps 10, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to 137 Mockingbird Cove! Modern, expansive home built in 2022, offering incomparable boating! Quick walk or ride from Sombrero Beach. Each of the 5 bedrooms features its own ensuite bathroom, offering ultimate privacy and comfort. Includes a private heated/chilled pool, 2 paddleboards, 4 bicycles,...

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$857
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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$560
avg per night

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Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Peace at 7 Knots... The newest house on Sombrero Beach Road! Be the first to stay at our lovely home. It is wonderfully decorated with a "more is less" clean style while at the same time having all that you will need in a single family home located in Marathon. Whether you are vacationing with...

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Featured review

"Great week in Marathon"

Had a great stay at this property. House is wonderful. Everything we needed was there! Ice machine outside for fishing came in very handy. House is clean and nice, outside is very nice with pool tiki hut...

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$500
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Key Lime Sunrise Watch the sunrise & feel the tropical breezes while sipping your coffee from the comfort of the upstairs screened terrace of this lovely and neatly maintained two bedroom two & a half bath home situated on Sombrero Beach Road. This charming getaway is within walking/biking distance...

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Featured review

"We had a very nice visit."

171 10th St. The duplex was very neat. We loved the screened in back porch (had to keep the fans going because of the heat). The pool chairs lacked comfort but we had seen that in the pictures and brought...

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$314
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Paraíso Del MarIntroducing our newest luxury vacation rental nestled in the prestigious community of Marathon. This brand-new build epitomizes elegance and sophistication, offering an unparalleled experience for those seeking the epitome of luxury in the Florida Keys.Set amidst lush tropical...

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$1,119
avg per night
Marathon Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This charming property offers 3 bedrooms and 2 bathrooms, ideal for families or groups looking to enjoy the beauty and tranquility of the Florida Keys.*Saturday-to-Saturday Rentals OnlyProperty Overview:Prime Location: Bird of Paradise offers stunning views of the Atlantic Ocean. Bird of...

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$336
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Charming 3-Bedroom, 2-Bathroom Duplex with Waterfront Views in Key Colony BeachEscape to this inviting ground-level duplex home in the heart of the beautiful Key Colony Beach. With stunning waterfront views, top-notch amenities, and plenty of space, this charming retreat is ideal for families or groups...

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Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Seaside SerenityWelcome to your exclusive luxury retreat in Marathon, Florida. Seaside Serenity is a brand-new, 4-bedroom 4.5-bathroom, private pool home where paradise meets perfection. With 35' of dockage and nestled in close proximity to the Atlantic Ocean, Gulf of Mexico, and Coco Plum Beach,...

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$928
avg per night
Marathon House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Updated two bedroom, two bathroom half duplex on 11th street. Excellent location towards the end of the canal yielding instant access to Vaca Cut and the Open Atlantic, 37 ft of deepwater dockage on an extra wide canal is perfect for fisherman and families alike! Enter through the street-side screened...

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$357
avg per night
Marathon Apartment
Sleeps 10, 5 bedrooms, 10 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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$871
avg per night
Marathon Apartment
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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$457
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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Featured review

"Great time"

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

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$489
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Family Fun on Manor Lane! Conveniently located in the heart of Marathon, this family getaway is everything you've been looking for! Spacious single family canal home with private swimming pool, deepwater dockage, and an inviting layout awaits for your arrival. Through the entry, you will find the...

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$471
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

4BR 4.5BA Home w/ Fantastic Outdoor Entertainment Area w/ Full Kitchen, Yard Games, Bikes, Kayaks, Paddleboards!Casa PlayaWelcome to Casa Playa, a luxurious 4-bedroom, 4.5-bathroom home in Marathon, Florida. Nestled behind gates in a 4-home enclave, this custom-designed retreat offers an element...

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Featured review

"Great week in marathon"

We had an amazing stay at this property from the moment we arrived, we were impressed with how immaculately clean and upscale the house was. The decor was beautiful, and everything felt fresh and well-maintained.The...

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$978
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

NEW!!! FULL BACKYARD REMODEL!!! NOW OPEN FOR BOOKING!!! INGROUND POOL INSTALLED HEATED! FIRE PIT! PUTTING GREEN! PRICES STILL REFLECT PRE RENOVATION PRICES HURRY IN BEFORE THEY GET RAISED! ***New backyard photos coming soon.***The Keys Hideaway ~ your private paradise in beautiful Marathon,...

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$362
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Property Overview:Prime Location: Caribbean Sunsets is nestled in a quiet and picturesque neighborhood, offering breathtaking waterfront living with open Gulf views. Enjoy lush tropical surroundings and easy proximity to local attractions, dining, shopping, and Sombrero Beach. *Saturday-to-Saturday...

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$621
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Adorable home just moments to the ocean. Lovely pool 10 X 20 (goes from 3′ to 5′) Pool heat is $200 add’l if paid in advance, or $250 on arrival plus taxes. 8 X 15 tiki to relax under the shade. 4 Flat screen TVs all w/DVD players. 55″ in L/R, 42″ in master bedroom and both...

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$362
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 2 bathrooms
15 reviews

Distance to beach: 2 miles to Sombrero Beach

Key Amenities

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

About this property

A beautiful waterfront half duplex home in a tropical setting with views of the Gulf of Mexico and incredible sunsets. Recently renovated octagonal shaped home with wide open water views from every window. Newly furnished comfortable interior with all the amenities you'd expect. Brick pavers surround...

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Featured review

"Best trip EVER!"

Will definitely be back to this house. The house was perfect! We saw manatees, lots of sea turtles, tropical fish and caught a tarpon! The house is ideally located and very private. We had a fabulous two...

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$365
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • WiFi

About this property

Welcome to Your Private Oceanfront Oasis in Marathon, Florida!Discover an unparalleled retreat in the heart of the Florida Keys where every day begins with breathtaking sunrises over turquoise waters. This charming oceanfront cottage effortlessly blends a relaxed beach vibe with upscale comforts,...

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$350
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 3 miles to Sombrero beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

If you are looking for a tropical Keyz experience, you have arrived in paradise at this three bedroom two bathroom home on a direct ocean access canal which has all the comforts of home and more. **This is a 3 bedroom 2 full bathroom rental** There is no ground floor apartment or access. This is owners...

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$249
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Distance to beach: 0.5 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Exclusive Sombrero Beach vacation retreat is located just up the street from one of the best beaches in the Florida Keys. Sombrero Beach is a large sandy beach that offers something for everyone in the family including playground, volleyball swimming and picnic tables. The beach is also a great place...

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$1,136
avg per night
Marathon House
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

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

About this property

Welcome to DragonFly Lite our home in Marathon, FL in the heart of the beautiful Florida Keys, the house has 2 bedrooms a Queen in the master and 2 twins in the guest room, one bathroom + our outdoor shower, all the towels you will need for the pool or beach (please leave the sand outside). It’s...

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Featured review

"A Magical Place to Isolate"

Though Dragonfly Lite would be a marvelous place to vacation anytime, it proved especially so in a global pandemic. We had everything we needed right there on property. The pool is pristine, the home was...

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$308
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Come and live the KeyZ life for the week or the month! Gorgeous home just off the open water on a deep water canal gulfside. This is a boater/fishing paradise with 60 feet of docking space, deluxe fish cleaning station located on the gulfside! Relax poolside at our signature swimming pool/tiki gar...

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Featured review

"Wonderful Rental"

We came with our family of 10 and had a wonderful time. The house was perfect for us. It is beautiful and spacious. The outdoor area is fantastic with a sun deck, two sofas and large sun umbrella. The...

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$527
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 3 bathrooms
9 reviews

Distance to beach: 2 miles to Sombrero Beach

Key Amenities

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

About this property

Waterfront Keys home with wide open view of the Gulf of Mexico. 3 Bedroom 3 bath, half-duplex home with private pool, dock with great amenities - perfect for three couples or a family. Great location that's walk-able to the 7-Mile bridge and some of Marathon's best restaurants and bars. Incredible...

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Featured review

"Our 10th year here!"

We absolutely love staying at this property! We rented a boat for the week this visit and it was so nice to walk past our private pool and jump in our boat or fish right off the dock. Manatees swim by almost...

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$376
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Off the HookImagine your vacation in this stunning custom-built modern 3-bed, 3-bath pool home, "Off the Hook," on the edge of Marathon. This newly built Florida Keys retreat welcomes you with a striking foyer and floor-to-ceiling windows that blend indoor luxury with outdoor beauty.The...

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$821
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
10 reviews

Key Amenities

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

About this property

4 bedroom/3 bath Canal front home.7 nights minimum. Enjoy coastal breezes in this canal front Villa. Beautifully decorated. 4 Bedrooms/3 Baths. Two King Master Suites with attached baths. One on first floor. Fully stocked Gourmet Kitchen. Dining area seats 10. Flat screen Satellite TV's in each...

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Featured review

"Well Done"

Very Clean, stocked with the right amenities, great location, very fun time, Would highly recommend for those looking for a central location in the Keys

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$513
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 1 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautifully updated 3 bedroom, 2 bathroom stilted home on exclusive Flamingo Island in the high-demand Sombrero Beach area. This home will not disappoint. Fantastically lush and meticulously landscaped yard by local famous design artist featuring a large, brand new heated/chilled pool with plenty of built...

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$468
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms

Distance to beach: 4 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

A Private And Convenient Piece of Paradise Awaits You In This Amazing 4 bedroom/ 3 bathroom Home Near Sombrero Beach. Our Home Is Located On A Deep Water Canal With Boat Access From The Yacht Club Boat Launch. ~KEY Z DREAMING~ Is Everything You Can Imagine With A Breathtaking Tiki Hut And Bar Located...

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$398
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Must See Stunning 3095 Sq. Ft 4/4 SFH on ground level with pool, 45 ft of dockage, outdoor kitchen and access to the ocean by boat.This gorgeous property features an open floor plan with elegant furnishings, state of the art kitchen with Viking appliances and an induction cooktop, quartz countertops,...

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Featured review

"Sunny Daze in Marathon!"

I didn’t know much about Marathon other than it was in the keys. Upon hearing from a family friend that it was the Keys best kept secret we couldn’t resist. The Sunny Daze house was perfect for my family...

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$1,199
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Mar Azul!You'll love this BRAND NEW custom-built home with beautiful open water ocean views and gorgeous sunsets. The 4 bedroom/4.5 bath layout offers 3 Masters with en suite bathrooms and walk-in closets. The door to the 4th bedroom area can be closed to create a private en suite...

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Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Slack Tide- 4 bedroom waterfront home with Private Pool,Outdoor Kitchen and DockWelcome to "Slack Tide", your dream vacation getaway in the heart of the Florida Keys! This luxurious 4-bedroom, 4.5-bath single-family home offers everything you need for an unforgettable stay. Nestled in a...

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Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

We welcome you to our piece of paradise in the heart of the Florida Keys! This ground level, SFH with a brand new pool & spa will guarantee to impress. Enjoy a cup of coffee or a cocktail while out back watching the birds, fish, manatees and sunrises/sunsets. This beautiful home offers 3 bedrooms...

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Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Private paradise! Gorgeous 4/3 Half duplex w/ private pool & dockage!Welcome to paradise at South Creek! This gorgeous 4/3 with a private pool and dockage welcomes you with its nautical decor. Enjoy the stunning sunsets/ sunrises from the balcony off of the living room with outside seating.This...

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Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Sea Renity~ Large 3/2 SFH, 30ft dockage, Private pool, Hot tub & Huge game roomWelcome to our lavishly appointed, open floor plan, 3/2 Single Family Home with water views from the living room and balcony. Easy boating access, less than 10 minutes from the Ocean. Seas the day and the evening breeze...

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