Luxury Florida Vacation Homes

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Coral Lagoon #18 ~ Tropical Retreat Lush palms, vibrant landscaping, and shaded lounge areas surround the resort-style pool, creating a peaceful tropical retreat for relaxing and soaking up the Florida Keys sunshine.

Coral Lagoon #18 ~ Tropical Retreat Enjoy tranquil canal views framed by mature palms and tropical greenery, creating a picturesque waterfront setting just steps from the home.

Coral Lagoon #18 ~ Tropical Retreat This spacious covered porch features natural wood decking, outdoor dining, and relaxing views of the surrounding tropical landscape.

Coral Lagoon #18 ~ Tropical Retreat Rich granite surfaces, warm wood cabinetry, and stainless-steel appliances create a welcoming kitchen designed for gathering and vacation meals.

Coral Lagoon #18 ~ Tropical Retreat Golden walls, natural wood finishes, and abundant sunlight create a bright and inviting space for cooking, dining, and spending time together.

Coral Lagoon #18 ~ Tropical Retreat Soft aqua walls, crisp white bedding, and natural wood accents create a bright and cheerful bedroom with a relaxed island atmosphere.

Coral Lagoon #18 ~ Tropical Retreat The spacious kitchen opens seamlessly to the living and dining areas, allowing everyone to stay connected while cooking and entertaining.

Coral Lagoon #18 ~ Tropical Retreat Natural light pours through surrounding windows and French doors, creating an inviting dining space for family meals and morning coffee.

8 guests 3 bed 2 bath 1,430 sq ft

The Keys - Marathon | Marathon

4.9 (16)

Guest rating

Starting at $163 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

Indigo Reef #39 ~ Sunset House Start your day with coffee or unwind at sunset from this private covered balcony overlooking the sparkling waters and tropical grounds of Indigo Reef.

Indigo Reef #39 ~ Sunset House Indigo Reef 39 Master Suite Private Deck Florida Keys Vacation Rental

Indigo Reef #39 ~ Sunset House The spacious kitchen features granite countertops, stainless steel appliances, and a breakfast bar that flows seamlessly into the living and dining areas.

Indigo Reef #39 ~ Sunset House This serene primary bedroom offers a king bed, abundant natural light, and direct access to a private balcony overlooking the Gulf.

Indigo Reef #39 ~ Sunset House Comfortable furnishings and an open layout create the perfect space to gather, relax, and enjoy the Florida Keys lifestyle.

Indigo Reef #39 ~ Sunset House Large glass doors invite natural light inside while providing easy access to the outdoor living spaces and waterfront views.

Indigo Reef #39 ~ Sunset House Thoughtfully designed with comfortable seating and tropical décor, this welcoming space is ideal for family gatherings.

Indigo Reef #39 ~ Sunset House Enjoy indoor-outdoor living with direct access to the covered balcony and scenic Gulf views beyond.

8 guests 3 bed 2 bath 1,600 sq ft

The Keys - Marathon | Marathon

5.0 (15)

Guest rating

Starting at $164 daily

Turtle Tides Private pool at luxury Florida Keys vacation rental with sunrise views over the water.

Turtle Tides Tropical pool deck with seating and waterfront views in Key Colony Beach, Florida Keys vacation rental.

Turtle Tides Relaxing tiki hut seating overlooking the water at Key Colony Beach Florida Keys vacation rental.

Turtle Tides Bright living room with large Smart TV and waterfront views at Key Colony Beach Florida Keys rental.

Turtle Tides Modern open-concept kitchen with ocean views at Key Colony Beach Florida Keys waterfront vacation rental.

Turtle Tides Spacious master suite with king bed, Smart TV, and tropical decor in Key Colony Beach Florida Keys vacation rental.

Turtle Tides Fully equipped modern kitchen with stainless steel appliances and ocean views in Key Colony Beach Florida Keys.

Turtle Tides Fully equipped kitchen with stainless steel appliances and granite countertops in Florida Keys vacation home.

9 guests 4 bed 3 bath 2,428 sq ft

The Keys - Other | Key Colony Beach

5.0 (6)

Guest rating

Starting at $243 daily

Key Vaca Stunning aerial perspective of a canal-front Florida Keys vacation home with private dock and direct Atlantic Ocean access, perfect for boating and family getaways.

Key Vaca Enjoy breathtaking canal and water views from this spacious balcony, featuring a dining table and comfortable seating for relaxing or alfresco meals in the Florida Keys.

Key Vaca Fully fenced private pool with stunning canal views, perfect for boating families.

Key Vaca Capture the full beauty of this canal-front rental from above, showing private dock, pool, and tropical surroundings with easy ocean access.

Key Vaca Modern cabinetry, stone countertops, and island seating inside a premier Florida Keys canal-front rental.

Key Vaca Comfort and privacy meet waterfront living in this beautifully furnished master suite.

Key Vaca Open-concept kitchen ideal for group stays, with waterfront views.

Key Vaca Large kitchen designed for extended stays, featuring full amenities and views of the canal.

10 guests 4 bed 3 bath 1,930 sq ft

The Keys - Marathon | Marathon

5.0 (1)

Guest rating

Starting at $220 daily

Casa de Rosa Stunning aerial view of a luxury Marathon Florida Keys waterfront vacation rental featuring a private pool, canal access, and tropical outdoor living.

Casa de Rosa Resort-style pool and hot tub in a Marathon FL vacation rental with comfortable loungers and canal views.

Casa de Rosa Relax in a tropical outdoor oasis with private pool and hot tub at this luxury Marathon Florida Keys vacation rental.

Casa de Rosa Spacious kitchen designed for entertaining in a Marathon FL waterfront vacation rental with easy access to the dining room and poolside patio.

Casa de Rosa Spacious master suite in a Marathon Florida Keys canal-front vacation rental featuring relaxing water views and easy access to the private pool.

Casa de Rosa Fully equipped kitchen in a luxury Marathon Florida vacation home with canal access, perfect for preparing fresh seafood after a day on the water.

Casa de Rosa Stylish kitchen in a Marathon Florida waterfront home with private pool and dock, ideal for cooking and entertaining during your Keys getaway.

Casa de Rosa Comfortable dining space in a Marathon Florida Keys canal-front vacation rental perfect for family meals after days spent boating and relaxing by the pool.

10 guests 4 bed 3 bath 2,217 sq ft

The Keys - Other | Key Colony Beach

5.0 (4)

Guest rating

Starting at $243 daily

Sombrero Sanctuary Enjoy your private fishing dock at this waterfront Marathon FL getaway, perfect for casting a line or taking in peaceful canal views. A great spot to relax after a day at Sombrero Beach or a Key West day trip.

Sombrero Sanctuary Relax in your private heated (on request) pool at this waterfront Marathon FL getaway, just minutes from Sombrero Beach. Perfect for families, this outdoor space is ideal for unwinding after a day on the water or a Key West day trip.

Sombrero Sanctuary Relax on your screened-in balcony overlooking the water, complete with a large outdoor TV for game days or movie nights. The perfect spot to unwind during your Marathon FL Florida Keys getaway.

Sombrero Sanctuary Bright and spacious open-concept kitchen overlooking the canal in this Marathon, Florida Keys vacation rental with private pool. Perfect for entertaining, the kitchen flows seamlessly into the dining area with stunning waterfront views.

Sombrero Sanctuary Unwind in the spacious primary suite with direct balcony access at this waterfront Marathon FL getaway. A peaceful retreat after a day at Sombrero Beach or exploring on a Key West day trip.

Sombrero Sanctuary Expansive open-plan kitchen with beautiful water views in a Marathon FL waterfront vacation rental. Designed for comfort and entertaining, this home offers a private pool and prime Florida Keys location.

Sombrero Sanctuary Fully equipped modern kitchen with waterfront views in a luxury Marathon FL vacation rental. This open-layout space connects to the dining room, making it ideal for guests seeking a Florida Keys waterfront home with pool.

Sombrero Sanctuary Enjoy cooking with breathtaking water views in this open-concept kitchen and dining space. Located in Marathon, Florida, this waterfront vacation rental offers a private pool and seamless indoor-outdoor island living.

10 guests 4 bed 2 bath 2,534 sq ft

The Keys - Marathon | Marathon

5.0 (3)

Guest rating

Starting at $201 daily

Bougainvillea Beauty Stretch out on poolside loungers and enjoy a relaxing Florida Keys getaway in this Marathon FL vacation home.

Bougainvillea Beauty This Marathon FL vacation home offers the perfect setup for families, with a private pool, dock, and plenty of space to relax and unwind.

Bougainvillea Beauty Retreat to the master suite featuring a king bed, private balcony access, and blackout curtains for restful nights during your Marathon FL getaway.

Bougainvillea Beauty This galley-style kitchen offers generous counter space and everything needed to prepare meals with ease during your Marathon FL Florida Keys getaway.

Bougainvillea Beauty Enjoy friendly competition with a ping pong table in the bonus game room, perfect for families and groups staying in Marathon FL.

Bougainvillea Beauty Designed for convenience and entertaining, this kitchen is perfect for preparing meals after a day at Sombrero Beach or exploring Marathon FL.

Bougainvillea Beauty Enjoy a spacious kitchen layout with ample prep space, ideal for families and groups staying in Marathon FL.

Bougainvillea Beauty Cook with ease in this fully equipped kitchen, featuring modern appliances and plenty of space for meal prep during your Florida Keys getaway.

8 guests 3 bed 2 bath 1,652 sq ft

The Keys - Marathon | Marathon

5.0 (1)

Guest rating

Starting at $251 daily

Cabana Cay This 3-bedroom, 2-bath Key Colony Beach half-duplex offers private dockage, a tiki hut, kayaks, pet-friendly accommodations, and Cabana Club access for a true Florida Keys getaway.

Cabana Cay Guests have access to the Cabana Club's pool, a favorite amenity for relaxing, swimming, and enjoying the private club atmosphere of Key Colony Beach.

Cabana Cay Relax under the private tiki hut overlooking the canal, complete with bar seating and a shaded outdoor space designed for laid-back Keys living.

Cabana Cay The fully equipped kitchen makes vacation dining easy, with everything you need for meals at home, plus both a Keurig and drip coffee maker for easy mornings in Key Colony Beach.

Cabana Cay Rest comfortably in the spacious primary bedroom, a peaceful and private escape in this pet-friendly Florida Keys vacation rental.

Cabana Cay Prepare breakfast before a day on the water or enjoy a relaxed dinner at home in this bright, functional kitchen at your Key Colony Beach Florida Keys getaway.

Cabana Cay The dining area offers a table with seating for 6, plus additional bar seating for 3, making it easy for families and groups to gather for meals in comfort.

Cabana Cay Enjoy shared meals and easy conversation in the open dining area, perfectly suited for group stays at this 3-bedroom Key Colony Beach vacation rental.

6 guests 3 bed 2 bath 1,325 sq ft

The Keys - Other | Key Colony Beach

Starting at $155 daily

Sunny Daze An overhead view highlights the rectangular pool, sun shelf, lounge chairs, brick patio, and screened lanai.

Sunny Daze This aerial view captures the canal front home, private pool, screened outdoor area, tropical yard, and waterfront dock.

Sunny Daze A large wooden dining table provides a comfortable setting for open-air meals inside the home's screened patio.

Sunny Daze Enjoy friendly competition in a spacious game room featuring a pool table, comfortable seating, coastal artwork, and bright windows.

Sunny Daze This spacious kitchen features dark wood cabinetry, granite countertops, stainless-steel appliances, and a large center island.

Sunny Daze A spacious dining table sits beside large windows in the bright, open-concept living area of this Marathon vacation rental.

Sunny Daze A large sectional and coastal decor create an inviting gathering space overlooking the open kitchen and dining area.

Sunny Daze .This bright living room features vaulted ceilings, comfortable seating, coastal artwork, a piano, and access to the screened patio.

10 guests 4 bed 4 bath 2,845 sq ft

The Keys - Marathon | Marathon

Starting at $248 daily

Manatee Manor The brick patio offers shaded tiki areas, outdoor seating, a grill, and a relaxing setting for enjoying the Florida Keys weather.

Manatee Manor Welcome to Manatee Manor, a charming canal front retreat with private dock access and relaxing Florida Keys outdoor spaces.

Manatee Manor This welcoming living area features sectional seating, a large television, tiled floors, and an open layout for relaxing together.

Manatee Manor Blue curtains and decorative pillows add coastal color to this comfortable bedroom with a ceiling fan and private bathroom access.

Manatee Manor Prepare vacation meals in a bright kitchen featuring granite countertops, a center island, wood cabinetry, and stainless-steel appliances.

Manatee Manor Prepare vacation meals in a bright kitchen featuring granite countertops, wood cabinetry, a center island, and stainless-steel appliances.

Manatee Manor A bright dining table and breakfast bar connect seamlessly with the kitchen, creating a comfortable space for shared meals.

Manatee Manor This spacious kitchen features a double sink, granite counters, wood cabinets, stainless-steel appliances, and bar seating.

6 guests 3 bed 2 bath 1,184 sq ft

The Keys - Other | Key Colony Beach

Starting at $184 daily

Man O' War Manor Adirondack chairs, tropical landscaping, a private pool, and direct dock access create an ideal Florida Keys outdoor retreat.

Man O' War Manor This aerial view highlights the home's coastal location, tropical surroundings, and proximity to open water.

Man O' War Manor A bright open floor plan connects the modern kitchen and living room, creating an inviting space for meals and group gatherings.

Man O' War Manor This open living area features generous seating, a coastal atmosphere, and easy access to the kitchen and waterfront patio.

Man O' War Manor This inviting primary bedroom features a cozy King bed, coastal furnishings, a ceiling fan, and sliding glass doors opening to a private waterfront balcony.

Man O' War Manor This spacious kitchen features white cabinetry, generous countertops, modern appliances, and a large island for preparing vacation meals.

Man O' War Manor A long breakfast bar, abundant cabinetry, built-in appliances, and bright finishes make this kitchen ideal for families and groups.

Man O' War Manor Gather around the large dining table in a bright coastal space that flows naturally into the kitchen and living room.

10 guests 4 bed 4 bath 2,679 sq ft

The Keys - Marathon | Marathon

Starting at $804 daily

Reel Relaxin A sweeping aerial view highlights this canal front retreat, private dock, pool, tropical grounds, and beautiful Florida Keys setting.

Reel Relaxin A large tropical pool and expansive brick patio provide the perfect setting for sunny days and waterfront relaxation.

Reel Relaxin This aerial perspective highlights the canal front dock, private pool, expansive patio, and tropical outdoor spaces.

Reel Relaxin Wake up to canal views in this bright bedroom featuring tropical decor, ample storage, and balcony access.

Reel Relaxin This spacious kitchen features rich wood cabinets, granite countertops, stainless-steel appliances, and abundant storage.

Reel Relaxin A spacious granite bar connects the kitchen and living area, offering extra seating and a convenient place for casual meals.

Reel Relaxin Expansive windows fill this coastal living room with natural light while offering relaxing views of the canal and tropical surroundings.

Reel Relaxin This expansive living room features comfortable seating, tropical decor, and large windows overlooking the waterfront.

12 guests 5 bed 4 bath 2,295 sq ft

The Keys - Marathon | Marathon

Starting at $303 daily