Luxury Florida Vacation Homes

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Paraiso Del Mar This impressive Marathon vacation home combines a private pool, multiple balconies, outdoor entertainment areas, and direct canal access.

Paraiso Del Mar Prepare and serve meals in a shaded outdoor kitchen with stone counters, bar seating, televisions, and waterfront breezes.

Paraiso Del Mar Relax around the outdoor table while enjoying wide canal views from the home's spacious upper balcony.

Paraiso Del Mar This expansive ground-level space offers cooking facilities, bar seating, televisions, ceiling fans, and easy access to the private pool.

Paraiso Del Mar Rest comfortably in a peaceful bedroom featuring coastal décor, natural light, and attractive views toward the canal.

Paraiso Del Mar Dramatic evening lighting illuminates the private pool, balconies, and covered outdoor living areas.

Paraiso Del Mar Challenge friends and family to a game of pool in this spacious recreation room with comfortable lounge seating.

Paraiso Del Mar Practice your short game on the private putting green surrounded by tropical landscaping and outdoor gathering areas.

12 guests 5 bed 4 bath 2,392 sq ft

The Keys - Marathon | Marathon

5.0 (12)

Guest rating

Starting at $495 daily

Villa Franchella Newly renovated luxury home with heated/chilled private pool and much more.

Villa Franchella Finding serenity by the canal`s edge: the perfect spot to unwind and watch the world float by.

Villa Franchella Above it all: Every sunrise and sunset paints a masterpiece, from this canal-side haven.

Villa Franchella Putting fun into every swing: where mini-golf magic awaits at every hole.

Villa Franchella Space for all adventures 5-6: Where parking is plentiful, whether for cars or trailers, fueling journeys both on land and water.

Villa Franchella Unwind in style: Where comfort meets technology, turning every evening into a cinematic escape.

Villa Franchella Sink into luxury: Where spacious sofas beckon, transforming every moment into pure relaxation.

Villa Franchella Unwind in style: Where comfort meets technology, turning every evening into a cinematic escape.

8 guests 4 bed 3 bath 1,561 sq ft

The Keys - Marathon | Marathon

5.0 (9)

Guest rating

Starting at $503 daily

Emerald Shores Enjoy a private, fenced pool area designed for fun and relaxation, surrounded by tropical landscaping and stunning Gulf vistas.

Emerald Shores Take a refreshing dip in this luxurious oceanfront saltwater pool, with the option to heat or chill the water to your preference.

Emerald Shores Luxury oceanfront vacation rental in Marathon, Florida Keys with tropical landscaping and Gulf views.

Emerald Shores Cook and entertain in style while overlooking the sparkling waters of the Gulf. This bright, airy kitchen offers direct access to the balcony for seamless indoor-outdoor dining.

Emerald Shores Breathtaking panoramic Gulf and Atlantic Ocean views from the luxury vacation rental in Marathon, Florida Keys.

Emerald Shores : Dock your boat conveniently at this private 60' slip with power and water, perfect for fishing excursions or exploring the Florida Keys.

Emerald Shores Prepare gourmet meals in this fully equipped, modern kitchen featuring stainless steel appliances, island seating for four, and sweeping Gulf views. Perfect for family vacations or group retreats.

Emerald Shores This stunning kitchen includes stainless steel appliances, ample counter space, and island seating—ideal for preparing fresh seafood after a day of Florida Keys fishing adventures.

12 guests 5 bed 4 bath 2,920 sq ft

The Keys - Marathon | Marathon

5.0 (3)

Guest rating

Starting at $390 daily

Sombrero Beach Beauty Relax and unwind beside your private heated pool surrounded by tropical landscaping and waterfront charm.

Sombrero Beach Beauty Comfortable seating and sunny poolside spaces create the perfect setting for island relaxation.

Sombrero Beach Beauty Enjoy direct canal access from your private dock, ideal for boating, fishing, and waterfront living.

Sombrero Beach Beauty Fully equipped with ample counter space and everything needed to prepare meals for family and friends.

Sombrero Beach Beauty Spacious and inviting, this comfortable bedroom offers a peaceful retreat after a day in the sun.

Sombrero Beach Beauty An aerial perspective showcasing the property's tropical setting, pool, and canal frontage.

Sombrero Beach Beauty Bright and airy living areas seamlessly connect for entertaining and relaxation.

Sombrero Beach Beauty Gather together beneath soaring ceilings with plenty of room for memorable meals.

12 guests 5 bed 3 bath 3,628 sq ft

The Keys - Marathon | Marathon

5.0 (16)

Guest rating

Starting at $427 daily

Seaside Serenity Experience resort-style living with a private pool, expansive grounds, and direct water access.

Seaside Serenity End the day around the fire pit while enjoying the peaceful waterfront atmosphere.

Seaside Serenity Your private dock offers front-row seats to spectacular sunsets and unforgettable evenings on the water.

Seaside Serenity Enjoy open-air dining, lounge seating, and seamless indoor-outdoor living overlooking the bay

Seaside Serenity Challenge friends to a game of pool while enjoying the tropical breeze and waterfront views.

Seaside Serenity A light-filled gathering space designed for relaxation after a day on the water.

Seaside Serenity Comfortable seating and abundant natural light create the perfect setting for unwinding

Seaside Serenity Designed for connection and comfort, with room for everyone to gather.

10 guests 4 bed 4 bath 2,040 sq ft

The Keys - Marathon | Marathon

5.0 (13)

Guest rating

Starting at $389 daily

Casa Playa Experience evening relaxation beside the private pool and beautifully illuminated outdoor living spaces at this canal front Marathon vacation rental.

Casa Playa Prepare and enjoy meals outdoors in a spacious covered kitchen featuring stainless-steel appliances, ample seating, and poolside access.

Casa Playa Launch a Florida Keys adventure directly from Casa Playa's canal front dock, complete with colorful paddle craft and calm-water access.

Casa Playa The bright indoor kitchen features expansive stone countertops, modern cabinetry, pendant lighting, and an open connection to the living area.

Casa Playa Unwind in a light-filled bedroom offering coastal décor, comfortable furnishings, and glass doors leading to a private outdoor space.

Casa Playa This bright private bathroom features a tiled walk-in shower, modern vanity, and stylish coastal accents.

Casa Playa Gather around the pool, outdoor kitchen, dining spaces, and canal front patio at this spacious Florida Keys vacation home.

Casa Playa Cook and entertain in a beautifully appointed kitchen with bar seating, stainless-steel appliances, and abundant natural light.

10 guests 4 bed 4 bath 2,176 sq ft

The Keys - Marathon | Marathon

4.9 (28)

Guest rating

Starting at $391 daily

Sunset Seeker Soak in breathtaking bay views from your private pool and spa surrounded by swaying palms.

Sunset Seeker Enjoy front-row seats to sparkling water views in this tropical outdoor retreat.

Sunset Seeker End each day with unforgettable sunsets and panoramic waterfront scenery.

Sunset Seeker Explore the surrounding waterways with included kayaks and easy water access.

Sunset Seeker Spacious and beautifully appointed, this kitchen is designed for gathering, cooking, and entertaining.

Sunset Seeker Wake up to stunning water views from this bright and inviting bedroom retreat.

Sunset Seeker Enjoy panoramic coastal scenery from this elevated perspective overlooking the bay.

Sunset Seeker Start your day with coffee and spectacular views from this spacious outdoor balcony.

8 guests 3 bed 3 bath 2,400 sq ft

The Keys - Marathon | Marathon

5.0 (4)

Guest rating

Starting at $382 daily

Blue Marlin House Showcasing generous dockage, pool and hot tub, and prime waterfront access in the Florida Keys.

Blue Marlin House Enjoy peace of mind with protected, secure boat docking at this waterfront home in Marathon, Florida Keys.

Blue Marlin House Designed for outdoor entertaining, this space combines a pool, hot tub, and outdoor kitchen with scenic water views.

Blue Marlin House Bright, modern kitchen with coastal charm.

Blue Marlin House Luxurious king bedroom with private ensuite bath and direct patio access in a waterfront Marathon vacation rental.

Blue Marlin House Spacious living room seamlessly connected to dining and kitchen, offering water views and comfort in a Florida Keys waterfront home.

Blue Marlin House Relax in this bright living space after a day at the beach or on the water, located just steps from Sombrero Beach.

Blue Marlin House Enjoy single-level living with easy access to bedrooms, kitchen, and outdoor areas.

8 guests 3 bed 3 bath 2,649 sq ft

The Keys - Marathon | Marathon

4.9 (12)

Guest rating

Starting at $304 daily

Paradise Point Relax in your own private oceanfront tiki hut, complete with shaded seating and uninterrupted ocean views. Perfect for afternoon cocktails or evening breezes, this tropical retreat offers a true Florida Keys experience just steps from the water.

Paradise Point Swim and unwind in your own private oceanfront pool surrounded by lush tropical landscaping. This luxury vacation rental in Marathon, Florida Keys, offers a serene escape with stunning water views and resort-style relaxation.

Paradise Point This spacious private yard offers sweeping views of the ocean, surrounded by tropical landscaping and swaying palms. A perfect outdoor retreat for families and couples to relax, play, and unwind in Marathon, FL.

Paradise Point Enjoy true island living with this oceanfront outdoor living area featuring shaded lounge seating, breezy palms, and direct access to the sea. Ideal for sunset cocktails, morning coffee, or casual outdoor dining.

Paradise Point This stunning oceanview kitchen is fully equipped and features panoramic water views, perfect for guests who enjoy cooking while surrounded by coastal beauty.

Paradise Point Enjoy hours of fun with this versatile 3-in-1 game table featuring ping pong, air hockey, and pool. Perfect for family game nights or friendly competitions during your Florida Keys vacation.

Paradise Point A chef's dream kitchen with granite countertops, stainless steel appliances, and breathtaking views of the Atlantic Ocean, all in a private Marathon vacation rental.

Paradise Point Prepare meals in this fully stocked kitchen and enjoy unobstructed ocean views from every angle, the perfect blend of luxury and comfort in the Florida Keys.

8 guests 3 bed 3 bath 1,910 sq ft

The Keys - Marathon | Marathon

5.0 (10)

Guest rating

Starting at $302 daily

Sunset Tides Relax on poolside on loungers or wade on the pool ledges while enjoying the breathtaking waterfront scenery at this Marathon FL rental.

Sunset Tides Relax poolside or enjoy the private dock with direct access to fishing, boating, and water adventures in this luxury rental.

Sunset Tides Experience the ultimate Marathon FL getaway in this spacious 5-bedroom, 4-bathroom waterfront rental featuring modern coastal décor and upscale amenities.

Sunset Tides Prepare meals with panoramic Gulf and Atlantic views in this luxury Marathon FL vacation home kitchen, featuring a fully stocked pantry, high-end appliances, and island seating.

Sunset Tides Relax in luxury with a heated pool, hot tub, and multiple outdoor seating areas overlooking the sparkling waters of Vaca Cut.

Sunset Tides Relax in this luxurious Marathon FL vacation home master suite with a king bed, Smart TV, and panoramic Gulf and Atlantic views—perfect for a romantic getaway or family retreat.

Sunset Tides Cook and entertain in style at this open-concept kitchen with Keurig Duo, Ninja food processor, and stunning water views, perfect for your Florida Keys family vacation.

Sunset Tides Enjoy the bright, airy kitchen at this oceanfront rental, complete with island seating for three and breathtaking water views for a luxury vacation experience.

12 guests 5 bed 4 bath 2,607 sq ft

The Keys - Marathon | Marathon

5.0 (3)

Guest rating

Starting at $334 daily

Emerald Horizon Exceptional luxury vacation home with a heated private pool located inside an exclusive Marathon FL community. Perfect for families seeking high-end Florida Keys accommodations with security, privacy, and top-tier amenities.

Emerald Horizon Bird's-eye view showcasing a premium waterfront property with pool, lanai, and boat slip leading directly to the Gulfside—ideal for boating, fishing, and family vacations in the Florida Keys.

Emerald Horizon Highlighting resort-style outdoor living, boat slip, and lush landscaping in a Gulf-access property.

Emerald Horizon Spacious master suite with king bed, private balcony access, and serene Gulf views—perfect for guests seeking upscale Florida Keys vacation rentals with pool.

Emerald Horizon Bright open-concept kitchen with island seating and designer finishes—steps from your private pool and outdoor living area. Perfect for families searching for upscale waterfront vacation rentals in Marathon, Florida Keys.

Emerald Horizon Spacious gourmet kitchen with high-end appliances, quartz counters, and water views—perfect for preparing meals during your Florida Keys luxury getaway.

Emerald Horizon Fully equipped chef's kitchen featuring stainless steel appliances and an open layout overlooking the heated pool and gulf views.

Emerald Horizon Beautifully updated kitchen with modern finishes and seamless flow to the wet bar, dining and coastal living area. Designed for guests seeking high-end Marathon FL vacation rentals with private amenities and resort-style comfort.

12 guests 5 bed 4 bath 2,392 sq ft

The Keys - Marathon | Marathon

5.0 (7)

Guest rating

Starting at $371 daily

8 guests 2 bed 2 bath 1,200 sq ft

Atlantic Coast - Amelia Island | Amelia Island

5.0 (6)

Guest rating

Starting at $249 daily

6 guests 2 bed 2 bath

Atlantic Coast - Other | Amelia Island

5.0 (2)

Guest rating

Starting at $325 daily

Beach Bliss Bright, bold, and bursting with personality, this 4-bedroom, 3-bathroom retreat feels like stepping into a living art gallery inspired by the beach, the sky, and everything that makes PCB unforgettable.

Beach Bliss Drift off under swaying palms after a long day in the sun.

Beach Bliss Perched high on the 9th floor of Majestic Beach Towers, this Panama City Beach condo isn't just where you stay—it's where vacation mode fully kicks in.

Beach Bliss This isn't just a condo. It's a colorful, high-energy beach escape where every room tells a story—and yours starts the moment you arrive.

Beach Bliss From the moment you walk in, color and creativity set the tone.

Beach Bliss Life-sized, vibrant artwork throughout the condo captures the energy of the shoreline and the surrounding area, making every room feel alive and intentional.

Beach Bliss Sink into plush seating and let the Gulf views steal the show—this is relaxation, perfected.

10 guests 4 bed 3 bath 1,583 sq ft

Panhandle - Panama City Beach | Panama City Beach

Starting at $186 daily

Aqua Vista Relax beside the expansive 16-by-32-foot private heated pool while enjoying sunshine, privacy, and the laid-back Florida Keys lifestyle.

Aqua Vista Enjoy 35 feet of dockage directly behind Aqua Vista, offering convenient canal access for your Florida Keys boating vacation.

Aqua Vista Gather in a soaring open-concept space connecting the kitchen, dining area, and living room beneath abundant natural light.

Aqua Vista The spacious first-floor primary bedroom features elegant coastal finishes, balcony access, a television, and a private full bathroom.

Aqua Vista The first-floor primary bathroom offers two sinks, ample counter space, bright lighting, and a glass-enclosed walk-in shower.

Aqua Vista Swim beneath colorful Florida Keys skies in a large private heated pool overlooking the home's tropical waterfront setting.

Aqua Vista A welcoming paver driveway, manicured landscaping, and graceful palms lead to this upscale Key Colony Beach vacation rental.

Aqua Vista Soaring ceilings, generous seating, waterfront windows, and an open staircase create an impressive yet comfortable gathering space.

8 guests 4 bed 4 bath 2,522 sq ft

The Keys - Other | Key Colony Beach

5.0 (19)

Guest rating

Starting at $284 daily

Mystic Waters Heated (on request) oceanfront pool with tiki hut and unobstructed open water views at Mystic Waters in Marathon, FL.

Mystic Waters Private pool deck surrounded by lush tropical landscaping overlooking the ocean in the Florida Keys.

Mystic Waters Outdoor dining and tiki hut seating area beside the oceanfront pool at this luxury Marathon vacation home.

Mystic Waters Primary suite with private balcony and sweeping ocean views in Marathon, FL.

Mystic Waters Open concept kitchen with ocean views connecting seamlessly to dining and living spaces.

Mystic Waters High-end chef's kitchen with modern coastal design and premium appliances at Mystic Waters.

Mystic Waters Bright, airy kitchen with natural light and stunning open water views.

Mystic Waters Spacious living room with unobstructed ocean views in this luxury Marathon vacation rental.

10 guests 4 bed 3 bath 1,701 sq ft

The Keys - Marathon | Marathon

4.8 (11)

Guest rating

Starting at $431 daily

Tranquil Tides Relax by your private pool surrounded by tropical landscaping and a spacious outdoor patio.

Tranquil Tides 75` dock with fish cleaning table.

Tranquil Tides Enjoy sweeping canal and Atlantic views from the private balcony off the primary suite.

Tranquil Tides Fully equipped kitchen with a center island for additional seating and surface.

Tranquil Tides Bright and airy primary suite featuring a king bed, sitting area, and balcony access.

Tranquil Tides Private boardwalk leading directly to the dock and waterfront.

Tranquil Tides Shaded outdoor cabana with dining space—perfect for relaxing after a day on the water

Tranquil Tides Heated private pool surrounded by lounge seating and tropical landscaping.

8 guests 4 bed 4 bath 2,640 sq ft

The Keys - Marathon | Marathon

5.0 (9)

Guest rating

Starting at $272 daily

Paradise Palms : Beautiful waterfront home featuring a private pool, expansive outdoor living spaces, and direct boating access in the Florida Keys.

Paradise Palms Relax poolside under sunny Florida skies in your private heated pool surrounded by comfortable lounge seating.

Paradise Palms Kayaks & paddleboards. Explore nearby waterways with included kayaks and paddleboards, perfect for island adventures right from the property.

Paradise Palms Bright and modern kitchen featuring premium finishes, spacious seating, and everything needed for memorable meals.

Paradise Palms Enjoy outdoor meals and tropical breezes while overlooking peaceful canal views from the covered balcony.

Paradise Palms Comfortable coastal-inspired guest room designed for restful nights after days spent exploring the Keys.

Paradise Palms Aerial perspective showcasing the private pool and spacious outdoor entertaining areas.

Paradise Palms Charming Florida Keys architecture with ample parking and easy access to all the home's amenities.

8 guests 3 bed 3 bath 2,640 sq ft

The Keys - Marathon | Marathon

5.0 (5)

Guest rating

Starting at $272 daily

Sunsets in Paradise Relax in the pool and hot tub while enjoying breathtaking views of the Gulf.

Sunsets in Paradise End each day with spectacular waterfront sunsets framed by swaying palms.

Sunsets in Paradise Gather around the fire pit and enjoy unforgettable evenings by the Gulf.

Sunsets in Paradise A shaded outdoor retreat featuring games, seating, and plenty of space to unwind.

Sunsets in Paradise Enjoy panoramic views of turquoise waters stretching to the horizon.

Sunsets in Paradise Lounge poolside beneath tropical palms in your private island oasis.

Sunsets in Paradise Cool off in the sparkling pool surrounded by lush landscaping and Gulf views.

Sunsets in Paradise Soak up the sunshine from this spacious waterfront pool retreat.

8 guests 3 bed 2 bath 2,016 sq ft

The Keys - Marathon | Marathon

4.8 (28)

Guest rating

Starting at $289 daily

Pier Pressure Stunning canal front retreat featuring a private pool, expansive outdoor living spaces, and breathtaking Florida Keys waterfront views.

Pier Pressure Relax by the sparkling private pool surrounded by tropical landscaping and spacious sun decks.

Pier Pressure Aerial view showcasing the home's exceptional waterfront setting with quick access to open water.

Pier Pressure Spacious lot with ample parking, private dockage, and panoramic canal views in the heart of the Keys.

Pier Pressure Enjoy sunny afternoons poolside surrounded by swaying palms and beautiful waterfront scenery.

Pier Pressure Spacious and inviting bedroom designed for comfort, relaxation, and restful nights after island adventures.

Pier Pressure Large guest suite featuring tropical décor, abundant natural light, and ample storage space.

Pier Pressure Comfortable accommodations complete with a large television and relaxing coastal atmosphere.

10 guests 4 bed 4 bath 3,200 sq ft

The Keys - Marathon | Marathon

5.0 (19)

Guest rating

Starting at $310 daily

Angler & Ale Relax poolside or soak in the hot tub after a day on the water.

Angler & Ale Deep-water dock with jet ski and kayak launch, just 10 minutes to open water via Sisters Creek.

Angler & Ale Enjoy movie nights in your own indoor theater room with bar, wine cooler, and seating just steps from the pool.

Angler & Ale Spacious pool deck ideal for kids, adults, and pets alike.

Angler & Ale Cook and entertain effortlessly in this open kitchen with modern appliances, drip coffee maker, and easy access to indoor and outdoor living areas.

Angler & Ale Spacious master bedroom overlooking the canal in a Florida Keys vacation rental.

Angler & Ale Bright, master bathroom with separate shower and tub, perfect for unwinding after a day on the water.

Angler & Ale Large kitchen ideal for family meals and entertaining, located in a premier Sombrero Isles waterfront vacation property.

10 guests 4 bed 3 bath 3,348 sq ft

The Keys - Marathon | Marathon

4.9 (18)

Guest rating

Starting at $256 daily

Paradise Found Enjoy the ultimate Florida Keys lifestyle with a private pool, canal frontage, and tropical landscaping just steps from the water.

Paradise Found Gather around the custom outdoor bar for refreshing drinks, waterfront breezes, and unforgettable evenings under the palms.

Paradise Found Beautifully illuminated at dusk, this private backyard oasis is perfect for relaxing after a day on the water.

Paradise Found Newly updated with elegant finishes, sparkling countertops, and an open layout designed for entertaining.

Paradise Found Soft coastal tones, tray ceilings, and expansive water views create a bright and welcoming gathering space.

Paradise Found Seamlessly connecting the living, dining, and kitchen areas for effortless vacation living and entertaining.

Paradise Found White cabinetry, abundant workspace, and modern appliances make preparing meals a pleasure.

Paradise Found Thoughtfully designed with upscale appliances and stylish coastal details throughout.

12 guests 5 bed 3 bath 2,150 sq ft

The Keys - Marathon | Marathon

5.0 (21)

Guest rating

Starting at $270 daily

Off the Hook Spectacular modern waterfront home featuring a private resort-style backyard and panoramic water views.

Off the Hook Expansive rooftop deck offering breathtaking open-water sunsets and endless waterfront views.

Off the Hook Gourmet kitchen with premium appliances, oversized island, and seamless indoor-outdoor entertaining.

Off the Hook Heated pool surrounded by luxury lounge seating, tropical landscaping, and outdoor living spaces.

Off the Hook Bird's-eye perspective showcasing the waterfront home, pool, dock, and tropical grounds.

Off the Hook Relax beside the sparkling pool while enjoying beautiful waterfront scenery.

Off the Hook Modern kitchen and living space looks directly over the water.

Off the Hook Deep-water dock with boat lift providing quick access to open water adventures.

8 guests 3 bed 3 bath 2,009 sq ft

The Keys - Marathon | Marathon

5.0 (35)

Guest rating

Starting at $316 daily

Casa Blanca A private backyard oasis featuring a refreshing plunge pool, tropical landscaping, and seamless indoor-outdoor living.

Casa Blanca Relax waterside with direct canal access, comfortable seating, and your private dock just steps away.

Casa Blanca Bold blue countertops and an open layout create a vibrant gathering space at the heart of the home.

Casa Blanca The primary suite offers a peaceful retreat with coastal-inspired décor and comfortable accommodations.

Casa Blanca A beautifully updated bathroom featuring sleek finishes and a spacious walk-in shower.

Casa Blanca Expansive counter space and open sightlines make entertaining effortless

Casa Blanca Designed for conversation and connection, this kitchen flows seamlessly into the living and outdoor spaces.

Casa Blanca Crisp white cabinetry and striking blue accents bring island charm to every meal.

8 guests 3 bed 3 bath 1,956 sq ft

The Keys - Other | Key Colony Beach

5.0 (10)

Guest rating

Starting at $359 daily

Reel Knotty Cool off in your private pool surrounded by tropical landscaping, lounge seating, and plenty of Florida sunshine.

Reel Knotty Spacious back porch at Marathon FL vacation rental with waterfront views and tropical breezes.

Reel Knotty Colorful kayaks available for guest use at waterfront vacation rental in Marathon Florida – launch right from your private dock into the calm, clear waters of the Florida Keys.

Reel Knotty Waterfront rental home with boat dock access in the Florida Keys.

Reel Knotty Modern kitchen with stainless steel appliances and granite countertops in Florida Keys rental.

Reel Knotty Open-concept living room with coastal decor and flat-screen TV in Marathon FL rental.

Reel Knotty Spacious master bedroom and king-size bed in Marathon vacation home.

Reel Knotty Welcoming entrance leads into the spacious open floor plan with views extending toward the waterfront.

10 guests 4 bed 4 bath 2,221 sq ft

The Keys - Marathon | Marathon

5.0 (19)

Guest rating

Starting at $286 daily

Casa Del Mar Perfect outdoor space for enjoying tropical evenings and family time.

Casa Del Mar Enjoy your private pool, fire pit, and outdoor living room in this luxury Keys retreat.

Casa Del Mar Ping pong, dominoes, cornhole, and kayaks make this waterfront home ideal for families and groups.

Casa Del Mar Fully equipped chef's kitchen featuring modern appliances and a Keurig coffee maker in a luxury waterfront home.

Casa Del Mar Comfortable king suite designed for relaxation and convenience.

Casa Del Mar Spacious kitchen ideal for entertaining, seamlessly connected to the great room and outdoor living areas.

Casa Del Mar Cook with ease in this well-appointed kitchen, perfect for preparing fresh local seafood.

Casa Del Mar Bright and functional kitchen just minutes from Sombrero Beach in the Florida Keys.

10 guests 4 bed 4 bath 1,992 sq ft

The Keys - Marathon | Marathon

5.0 (25)

Guest rating

Starting at $334 daily

Sea Glass Dreams Stunning aerial view showcasing this canal-front property with private dock, pool, and tropical surroundings.

Sea Glass Dreams Bird's-eye perspective highlighting the home's desirable waterfront setting in the heart of the Florida Keys.

Sea Glass Dreams Enjoy friendly competition with the arcade-style basketball game, perfect for guests of all ages.

Sea Glass Dreams Fully equipped kitchen ready for your culinary creations.

Sea Glass Dreams Master suite with a king bed and an en-suite bathroom.

Sea Glass Dreams Practice your short game on the private putting green alongside the sparkling pool.

Sea Glass Dreams Master suite with a king bed and an en-suite bathroom.

Sea Glass Dreams Master suite with a king bed and an en-suite bathroom.

12 guests 5 bed 4 bath 2,526 sq ft

The Keys - Marathon | Marathon

4.9 (18)

Guest rating

Starting at $314 daily

Refuge on the Reef Unwind in the shade with a hammock, picnic seating, and views of the private pool.

Refuge on the Reef 46` swimming pool with Tiki hut, Hammock, and plenty of seating

Refuge on the Reef Relax on the screened patio with comfortable seating and refreshing views of the pool area.

Refuge on the Reef Prepare family meals in this bright kitchen featuring generous cabinetry, modern appliances, and ample counter space.

Refuge on the Reef Rest comfortably in this inviting bedroom featuring a king bed, calming finishes, and abundant storage.

Refuge on the Reef Challenge the family to a game of table tennis in this shaded outdoor entertainment area.

Refuge on the Reef Cook outdoors and gather for relaxed meals beside the private pool and tropical landscaping.

Refuge on the Reef A bird's-eye perspective showcases the large pool, tiki pavilion, and spacious surrounding deck.

14 guests 6 bed 5 bath 2,636 sq ft

The Keys - Marathon | Marathon

4.8 (23)

Guest rating

Starting at $275 daily

Tranquil Retreat Unwind beneath the palms with a hammock and shaded seating in your private tropical backyard.

Tranquil Retreat Enjoy an incredible location near the beach, open water, and all the best of Key Colony Beach.

Tranquil Retreat Resort-style pool at Cabana Club in Key Colony Beach, Florida Keys — a luxury vacation destination with palm-lined pool deck, tropical ambiance, and easy access to beaches, boating, and island activities.

Tranquil Retreat A beautifully updated kitchen featuring granite countertops, modern finishes, and bar seating.

Tranquil Retreat Relax in a comfortable primary bedroom with coastal décor and abundant natural light.

Tranquil Retreat Launch a waterfront adventure with complimentary kayaks ready for your use.

Tranquil Retreat Direct canal access makes it easy to enjoy boating, fishing, and exploring the Keys.

Tranquil Retreat The kitchen and living spaces connect seamlessly for gathering and entertaining.

6 guests 4 bed 2 bath 1,368 sq ft

The Keys - Other | Key Colony Beach

5.0 (14)

Guest rating

Starting at $287 daily

Oceanside Manor Beautifully maintained waterfront home with classic Florida Keys architecture.

Oceanside Manor Expansive 14' x 64' pool perfect for swimming, lounging, and entertaining

Oceanside Manor Enjoy morning coffee or sunset cocktails while overlooking peaceful canals and tropical scenery.

Oceanside Manor Gather for memorable meals in a bright and sophisticated dining area filled with natural light.

Oceanside Manor A relaxing retreat featuring generous space, soft coastal tones, and direct access to outdoor living areas.

Oceanside Manor Experience the unique beauty of island living with panoramic views of canals leading to open water.

Oceanside Manor Designed for entertaining, this chef-inspired kitchen features expansive granite counters and abundant workspace.

Oceanside Manor Thoughtfully decorated with soothing colors and comfortable furnishings for restful nights after days in the sun.

10 guests 5 bed 3 bath 3,600 sq ft

The Keys - Other | Key Colony Beach

5.0 (3)

Guest rating

Starting at $271 daily

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