Luxury Florida Vacation Homes

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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

Casa Tranquilo Relax beside the spacious private pool while enjoying sunshine, lounge seating, and the tropical atmosphere of this Marathon vacation rental.

Casa Tranquilo This aerial view showcases the home's private pool, waterfront location, dockage, and expansive outdoor living areas.

Casa Tranquilo Prepare vacation meals in a bright kitchen featuring abundant cabinetry, modern appliances, generous counters, and convenient storage.

Casa Tranquilo Rest comfortably in a spacious bedroom with a television, ceiling fan, dresser storage, and warm Florida Keys styling.

Casa Tranquilo This convenient bathroom features a spacious vanity, shower and tub combination, and cheerful aqua coastal finishes.

Casa Tranquilo Enjoy casual meals and morning coffee at the curved breakfast bar connecting the kitchen to the home's living spaces.

Casa Tranquilo The well-equipped kitchen offers extensive cabinetry, full-size appliances, abundant preparation space, and breakfast-bar seating.

Casa Tranquilo Cool off in the sparkling private pool or relax beneath the shaded arches overlooking the waterfront backyard.

8 guests 3 bed 4 bath 2,251 sq ft

The Keys - Marathon | Marathon

4.8 (13)

Guest rating

Starting at $183 daily

Kon Tiki Cool off in your private pool surrounded by tropical landscaping and island charm.

Kon Tiki Expansive backyard & ample seating

Kon Tiki Vaulted ceilings and expansive windows fill this open-concept living space with natural light.

Kon Tiki Private 30-foot dock with easy canal access, perfect for boating and fishing adventures.

Kon Tiki Single family stilted home, plenty of privacy & walking distance to Sombrero Beach

Kon Tiki Bright and airy gathering area designed for comfort and connection.

Kon Tiki Relax in comfortable seating beneath soaring ceilings and island-inspired décor.

Kon Tiki Open dining area that seamlessly connects to the living room and kitchen.

8 guests 3 bed 2 bath 1,404 sq ft

The Keys - Marathon | Marathon

4.9 (29)

Guest rating

Starting at $194 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

Island Time Cool off in your private pool while enjoying the ultimate Florida Keys waterfront lifestyle. Your 176sqft private pool.

Island Time 32` dock, canal depth abour 3-4` deep when low tide.

Island Time Granite countertops, modern appliances, and open sightlines make every meal a memorable occasion.

Island Time Unwind in the spacious primary bedroom with easy access to waterfront views and outdoor living.

Island Time Clean lines, natural stone tile, and a bright vanity create a relaxing retreat for your daily routine.

Island Time he perfect spot for morning coffee before heading out for a day on the water.

Island Time Gather, relax, and create vacation memories in this bright and welcoming great room.

Island Time Thoughtful design and beach-inspired décor create a warm and inviting atmosphere.

8 guests 3 bed 2 bath 1,392 sq ft

The Keys - Marathon | Marathon

4.9 (29)

Guest rating

Starting at $205 daily

Adventures In Paradise Relax beside the sparkling private pool at Adventures in Paradise, a tropical Marathon vacation rental near Sombrero Beach.

Adventures In Paradise Enjoy direct waterfront living from the private canal dock, an inviting spot for launching kayaks or relaxing by the water.

Adventures In Paradise Prepare vacation meals in a spacious kitchen featuring granite countertops, dark cabinetry, stainless-steel appliances, and an open layout.

Adventures In Paradise Unwind in a bright coastal bedroom with tropical décor, wood-look flooring, ample natural light, and comfortable furnishings.

Adventures In Paradise Get ready comfortably with dual sinks, granite counters, abundant storage, bright lighting, and a large wall mirror.

Adventures In Paradise Gather in a bright open-concept space connecting the kitchen, dining area, and comfortable living room at this Florida Keys rental.

Adventures In Paradise Share meals around the welcoming dining table, conveniently positioned beside the kitchen in this spacious Marathon vacation home.

Adventures In Paradise This fully equipped kitchen offers granite counters, stainless-steel appliances, generous cabinetry, and plenty of room for vacation cooking.

10 guests 4 bed 3 bath 1,840 sq ft

The Keys - Marathon | Marathon

4.9 (16)

Guest rating

Starting at $199 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 $303 daily

Gone Coastal Enjoy the 18' x 26' heated pool surrounded by swaying palms, shade sails, and comfortable lounge seating in a private tropical setting.

Gone Coastal The sparkling pool is framed by lush landscaping and mature palms, creating a relaxing outdoor retreat for swimming and sunbathing.

Gone Coastal This beautifully updated kitchen features white cabinetry, stainless steel appliances, quartz countertops, and ample space for meal preparation.

Gone Coastal The primary suite offers a king bed, coastal-inspired décor, and direct access to a private balcony overlooking the tropical surroundings.

Gone Coastal This full guest bathroom features bright finishes, a walk-in shower, and convenient access from the main living level.

Gone Coastal Challenge friends and family to a game of pool in this spacious recreation room designed for indoor fun and relaxation.

Gone Coastal The open-concept layout connects the kitchen, dining area, and living room, creating a bright space for gathering and entertaining.

Gone Coastal Comfortable seating, a pool table, and plenty of open space make this the perfect spot for games, conversation, and downtime.

10 guests 4 bed 4 bath 2,498 sq ft

The Keys - Marathon | Marathon

4.7 (13)

Guest rating

Starting at $244 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

Seas the Day A stunning aerial perspective showcasing the home's canal-front location, private pool, and tropical outdoor spaces.

Seas the Day Dine al fresco by the poolside accompanied by the refreshing ambiance of water and sunshine.

Seas the Day Take a dip in our private heated pool oasis, offering a cozy retreat with dimensions of 10ft x 20ft and a depth of 5ft.

Seas the Day Unwind in our poolside lounge area on the ground level.

Seas the Day Effortlessly transition from cooking to dining: a fully-equipped kitchen adjacent to the inviting dining area.

Seas the Day Aerial views.

Seas the Day Easy access to your own 50` dock right at the backyard.

Seas the Day Aerial views.

8 guests 3 bed 2 bath 1,080 sq ft

The Keys - Marathon | Marathon

5.0 (37)

Guest rating

Starting at $191 daily

Sea Glass Cottage Aerial perspective showcasing this charming Keys getaway just moments from the water.

Sea Glass Cottage Airy elegance: Open-concept living, kitchen, and dining area beneath soaring ceilings.

Sea Glass Cottage Comfort meets relaxation. Lounge on the deck with cozy sofas and sun chairs.

Sea Glass Cottage Sunny comfort: Twin beds and a functional workspace in a cozy, sunlit loft setting.

Sea Glass Cottage Modern kitchen complete with all the essentials for culinary creativity.

Sea Glass Cottage Airy elegance: Open-concept living, kitchen, and dining area beneath soaring ceilings.

Sea Glass Cottage Airy elegance: Open-concept living, kitchen, and dining area beneath soaring ceilings.

Sea Glass Cottage Modern kitchen equipped with washer and dryer for added convenience.

6 guests 2 bed 2 bath 1,470 sq ft

The Keys - Marathon | Marathon

4.9 (18)

Guest rating

Starting at $87 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

Indigo Reef #50 ~ The Palms Relax on the private covered porch while enjoying palm-framed views across the lawn toward the beautiful Gulf of Mexico.

Indigo Reef #50 ~ The Palms Swim beneath swaying palms in Indigo Reef's expansive community pool, surrounded by loungers and tropical landscaping.

Indigo Reef #50 ~ The Palms Comfortable rocking chairs make this shaded porch a peaceful spot for morning coffee or evening conversation.

Indigo Reef #50 ~ The Palms The fully equipped kitchen connects effortlessly to the dining and living spaces, creating an inviting setting for group gatherings.

Indigo Reef #50 ~ The Palms Rest comfortably in a bright primary bedroom featuring coastal furnishings, ample storage, and convenient bathroom access.

Indigo Reef #50 ~ The Palms A palm-lined lawn and waterfront pathway frame tranquil views toward the turquoise waters beyond the resort.

Indigo Reef #50 ~ The Palms Gather around the large wooden dining table with easy access to the open kitchen, living room, and outdoor porch.

Indigo Reef #50 ~ The Palms The spacious granite breakfast bar provides a convenient place for casual meals, serving drinks, or chatting with the cook.

8 guests 3 bed 2 bath 1,600 sq ft

The Keys - Marathon | Marathon

4.9 (16)

Guest rating

Starting at $193 daily

Indigo Reef #57 ~ Turtle Cove Shared pool, heated 5 feet salt but all salt pools do have some chlorine.

Indigo Reef #57 ~ Turtle Cove Convenient dock slips within the community. Dock no. 56, not pictured, is included in your rental.

Indigo Reef #57 ~ Turtle Cove Whip up culinary magic in this fully-equipped kitchen.

Indigo Reef #57 ~ Turtle Cove The master suite connected to the balcony with stunning ocean views.

Indigo Reef #57 ~ Turtle Cove Relax and unwind with stunning ocean views.

Indigo Reef #57 ~ Turtle Cove Whip up culinary magic in this fully-equipped kitchen.

Indigo Reef #57 ~ Turtle Cove A seamless blend of living, dining, and kitchen spaces, perfect for creating unforgettable memories together.

Indigo Reef #57 ~ Turtle Cove To the left is the half bathroom, stairs up to the 2nd floor accessed directly from the living room.

8 guests 3 bed 2 bath 1,600 sq ft

The Keys - Marathon | Marathon

4.8 (31)

Guest rating

Starting at $144 daily

Keys Dream Step outside to your private canal frontage with 37 feet of dockage and quick boating access to open water.

Keys Dream A beautifully updated kitchen with coastal finishes, generous prep space, and room for everyone to gather.

Keys Dream Enjoy peaceful canal views right from the comfort of this bright and inviting guest bedroom.

Keys Dream Guests enjoy membership privileges to the Glunz Beach & Pool Club for an added resort-style experience.

Keys Dream Paddleboards and bikes are ready for exploring the neighborhood and nearby waterways.

Keys Dream The oversized kitchen island creates the perfect space for morning coffee, happy hour, and casual meals..

Keys Dream Open-concept living and dining spaces make entertaining effortless after a day on the water.

Keys Dream Bright cabinetry, modern appliances, and abundant seating make this kitchen the heart of the home.

6 guests 3 bed 2 bath 1,333 sq ft

The Keys - Other | Key Colony Beach

5.0 (15)

Guest rating

Starting at $163 daily

Indigo Reef #5 ~ Tarpon Terrace Shared pool, heated 5 feet salt but all salt pools do have some chlorine.

Indigo Reef #5 ~ Tarpon Terrace Peaceful marina lined with waterfront residences—keep an eye out for visiting manatees.

Indigo Reef #5 ~ Tarpon Terrace Fully equipped kitchen featuring granite countertops, stainless appliances, and everything needed for home-cooked meals.

Indigo Reef #5 ~ Tarpon Terrace Spacious primary suite featuring a king bed and private balcony overlooking the tropical grounds.te porch.

Indigo Reef #5 ~ Tarpon Terrace Bright open-concept kitchen flowing seamlessly into the dining space for effortless entertaining.

Indigo Reef #5 ~ Tarpon Terrace Gather around the large dining table, perfect for family dinners and game nights.

Indigo Reef #5 ~ Tarpon Terrace Granite breakfast bar overlooking the expansive living and dining areas.

Indigo Reef #5 ~ Tarpon Terrace Spacious main level with an open layout ideal for relaxing and entertaining.

8 guests 3 bed 2 bath 1,690 sq ft

The Keys - Marathon | Marathon

4.9 (11)

Guest rating

Starting at $286 daily

Indigo Reef #48 ~ Pirates Cove This aerial perspective showcases the beautifully maintained waterfront community, private marina, resort amenities, and direct access to the turquoise waters of the Florida Keys.

Indigo Reef #48 ~ Pirates Cove Relax beside the sparkling community pool framed by towering palm trees, spacious sun decks, and lush tropical landscaping.

Indigo Reef #48 ~ Pirates Cove This spacious king suite features soothing coastal tones, abundant natural light, and direct access to a private balcony overlooking the resort grounds.

Indigo Reef #48 ~ Pirates Cove Enjoy a bird's-eye view of the marina, resort amenities, and surrounding waterways that make this Florida Keys destination so desirable.

Indigo Reef #48 ~ Pirates Cove The resort map provides a helpful overview of the community, including pool areas, marina access, walking paths, and nearby amenities.

Indigo Reef #48 ~ Pirates Cove Prepare family meals with ease in this spacious kitchen featuring granite countertops, stainless steel appliances, and generous cabinet storage.

Indigo Reef #48 ~ Pirates Cove The well-appointed kitchen offers ample workspace, modern appliances, and everything needed for extended stays and entertaining.

Indigo Reef #48 ~ Pirates Cove Open to the living and dining areas, this inviting kitchen creates the perfect space for preparing meals and spending time together.

8 guests 3 bed 2 bath 1,600 sq ft

The Keys - Marathon | Marathon

4.7 (6)

Guest rating

Starting at $149 daily

My Beach Key Relax beneath the tiki hut and enjoy front-row views of the wide canal just steps from the home.

My Beach Key Enjoy membership privileges to the prestigious glunz Beach & Pool Club during your stay.

My Beach Key An open-concept living area designed for entertaining, relaxing, and reconnecting.

My Beach Key Spacious seating, canal views, and a sleeper sofa provide comfort for everyone.

My Beach Key Warm wood ceilings and coastal décor create a relaxed Florida Keys atmosphere.

My Beach Key Gather with family and friends in this inviting living space filled with natural light.

My Beach Key A charming dining area where island meals and memories come together.

My Beach Key Open sightlines connect the dining room, kitchen, and living areas effortlessly.

6 guests 2 bed 2 bath 1,000 sq ft

The Keys - Other | Key Colony Beach

4.9 (7)

Guest rating

Starting at $109 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

Seaside Villa This aerial view showcases the property's prime oceanfront location, where clear turquoise water, tropical landscaping, and waterfront amenities create the perfect Florida Keys escape.

Seaside Villa From above, the stunning coastline reveals miles of shoreline bordered by crystal-clear water on one side and protected natural beauty on the other.

Seaside Villa This aerial perspective highlights the property's oceanfront setting, community pools, private beach area, and direct access to the sparkling waters below.

Seaside Villa The sparkling waterfront pool offers stunning ocean views, tropical palm trees, and plenty of space to relax while enjoying the warm Florida Keys sunshine.

Seaside Villa A peaceful stretch of shoreline meets calm turquoise water, creating the perfect setting for beach walks, sunrises, and oceanfront relaxation.

Seaside Villa This charming tiki hut provides a shaded retreat just steps from the water, offering a peaceful place to enjoy sea breezes and panoramic ocean views.

Seaside Villa Enjoy access to the community tennis court, surrounded by tropical landscaping and conveniently located within the oceanfront property grounds.

Seaside Villa This aerial view showcases the property's prime waterfront location, featuring direct beach access, a community pool, and breathtaking ocean views.

6 guests 2 bed 2 bath 1,280 sq ft

The Keys - Marathon | Marathon

4.9 (34)

Guest rating

Starting at $101 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

Dolphin Cove This aerial view showcases Dolphin Cove's tropical setting near the marina, resort grounds, and beautiful Florida Keys coastline.

Dolphin Cove Cool off in a sparkling community pool surrounded by tropical palms, lounge space, and a shaded tiki pavilion.

Dolphin Cove Prepare vacation meals in a convenient kitchen featuring granite countertops, full-size appliances, generous cabinetry, and marina views.

Dolphin Cove Unwind in a bright bedroom with a comfortable bed, television, ceiling fan, ample storage, and sliding doors leading outside.

Dolphin Cove This elevated perspective identifies the unit within its peaceful waterfront community near boats, tropical grounds, and open water.

Dolphin Cove Relax on a comfortable sectional in a bright living space connected to the dining area and waterfront balcony.

Dolphin Cove A cheerful hallway with marine-inspired décor welcomes guests into this comfortable two-bedroom Marathon retreat.

Dolphin Cove The open great room combines comfortable seating, a dining table, and glass doors framing beautiful waterfront views.

6 guests 2 bed 2 bath 1,464 sq ft

The Keys - Marathon | Marathon

4.9 (12)

Guest rating

Starting at $103 daily

Flamingo Bay Relax beside the sparkling private pool, surrounded by tropical landscaping, lounge seating, and a spacious waterfront patio.

Flamingo Bay Aerial View of Flamingo Bay Pool and Canal

Flamingo Bay This overhead perspective showcases the home's private pool, tropical backyard, patio, dock, and canal frontage.

Flamingo Bay Unwind in a cheerful living room featuring vaulted ceilings, colorful furnishings, a large television, and patio access.

Flamingo Bay Wake to tropical views in a comfortable bedroom with soft coastal furnishings and glass doors leading toward the pool.

Flamingo Bay Share meals beneath a woven pendant light in a charming dining area decorated with colorful marine artwork.

Flamingo Bay The centrally located dining table provides an inviting gathering space between the kitchen and coastal living room.

Flamingo Bay Two twin beds, colorful linens, a ceiling fan, and convenient storage make this room ideal for children or additional guests.

5 guests 2 bed 2 bath 1,016 sq ft

The Keys - Other | Key Colony Beach

5.0 (6)

Guest rating

Starting at $153 daily

Tiki Time Relax beneath the tiki hut while taking in sweeping views of the sparkling pool and tropical backyard oasis.

Tiki Time Stretch out under the thatched roof and enjoy cool shade just steps from the pool and waterfront.

Tiki Time A favorite place to share meals, cocktails, and stories beneath authentic island-style charm.

Tiki Time Private dock with direct canal access, perfect for boating adventures and waterfront living.

Tiki Time Open-concept living and dining spaces designed for comfort, connection, and coastal relaxation.

Tiki Time Unwind in this inviting king bedroom featuring soothing beach-inspired décor and natural light.

Tiki Time Spend your days lounging poolside in a private tropical setting designed for relaxation.

Tiki Time Gather around the picnic table for waterfront meals in a true Florida Keys atmosphere.

8 guests 3 bed 2 bath 1,326 sq ft

The Keys - Marathon | Marathon

5.0 (14)

Guest rating

Starting at $191 daily

Adventures in Sombrero Discover a spacious waterfront vacation home on Sombrero Beach Road in Marathon, Florida, featuring a private pool, canal access, dock, and tropical outdoor spaces in the heart of the Florida Keys.

Adventures in Sombrero Take in peaceful canal and neighborhood views from the elevated balcony of this Sombrero Beach Road vacation rental.

Adventures in Sombrero Relax beside the private pool on a spacious brick patio at this vacation rental near Sombrero Beach in Marathon.

Adventures in Sombrero This modern Marathon kitchen includes stainless-steel appliances, dark wood cabinetry, and easy access to a nearby bedroom.

Adventures in Sombrero Relax in a spacious bedroom with a comfortable bed, writing desk, ceiling fan, and abundant Florida sunshine.

Adventures in Sombrero Prepare family meals in a well-equipped kitchen featuring dark cabinetry, stainless-steel appliances, and recessed lighting.

Adventures in Sombrero A spacious granite breakfast bar connects the kitchen and living areas, providing extra room for dining and entertaining.

Adventures in Sombrero Gather in a welcoming blue-accented living room with generous seating and easy access to the home's outdoor spaces.

10 guests 4 bed 3 bath 1,888 sq ft

The Keys - Marathon | Marathon

5.0 (8)

Guest rating

Starting at $218 daily

Reel Deal Relax in your private waterfront pool surrounded by tropical landscaping and plenty of space for sunbathing and outdoor fun.

Reel Deal Aerial view showcasing the home's desirable canal-front setting with quick boating access to open water.

Reel Deal Complimentary kayaks make it easy to explore the scenic waterways and enjoy unforgettable Florida Keys adventures.

Reel Deal Bright and inviting entryway opens to a fully equipped kitchen designed for comfort and convenience.

Reel Deal Comfortable bedroom featuring coastal-inspired décor, quality furnishings, and a relaxing atmosphere.

Reel Deal Spacious layout seamlessly connects the living room, kitchen, and outdoor entertaining spaces.

Reel Deal Fully equipped kitchen with stainless steel appliances, ample cabinetry, and generous counter space.

Reel Deal Gather with family and friends around the dining table for meals, games, and memorable conversations.

10 guests 4 bed 3 bath 1,213 sq ft

The Keys - Marathon | Marathon

4.9 (19)

Guest rating

Starting at $200 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