Luxury Florida Vacation Homes

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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

SEA-Renity at Prominence 30A Street view showing the second floor balcony above the garage and the covered front porch.

SEA-Renity at Prominence 30A Two cushioned wicker chairs on the front porch, a good spot for morning coffee with the dog at your feet.

SEA-Renity at Prominence 30A Bright entry with glass French doors, board wainscot, and light oak floors that run through the house.

SEA-Renity at Prominence 30A Vaulted entry hall with a bench for bags and shoes, and a run of windows that keeps it sunlit.

SEA-Renity at Prominence 30A Great room opens to the kitchen and dining, with two full sofas so all 14 guests fit in one space.

SEA-Renity at Prominence 30A Rattan and upholstered chairs at the dining table, with the living room and TV in the same sight line.

SEA-Renity at Prominence 30A White shaker kitchen with a quartz island for five, gas cooktop, stainless hood, and stacked wall ovens.

SEA-Renity at Prominence 30A Island seating for five faces the dining table, so whoever is cooking is never cut off from the group.

14 guests 4 bed 4 bath 1,090 sq ft

Panhandle - Other | Inlet Beach

Starting at $150 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

Parrish Point 472 - Petey's Place Sit back and unwind while taking in the incredible views

Parrish Point 472 - Petey's Place Spacious pool area to soak up the sun or cool off on a warm day

Parrish Point 472 - Petey's Place A relaxing living room with a direct view of the outdoor pool area

Parrish Point 472 - Petey's Place A bright and welcoming kitchen with high-end appliances for cooking convenience

Parrish Point 472 - Petey's Place Cozy master bedroom with calming colors and plenty of natural light

Parrish Point 472 - Petey's Place Enjoy the peaceful pier with stunning views of the water

Parrish Point 472 - Petey's Place Open and airy sunroom with fantastic pool and nature views

Parrish Point 472 - Petey's Place Enjoy 1 free adult activity admission daily (value over $500)! Not available for stays 27+ days.

13 guests 4 bed 2 bath 3,100 sq ft

Panhandle - Other | Mary Esther

Starting at $183 daily

Coral Reef Club 49 Enjoy endless Gulf views from this airy living space – where every sunrise and sunset feels front-row.

Coral Reef Club 49 Whether it's breakfast, lunch, or a sunset dinner, every meal comes with front-row Gulf views and a splash of coastal color.

Coral Reef Club 49 Cool off in the sparkling community pool just steps from your stay. With plenty of lounge chairs, a shallow entry, and sunny patio space, it's the perfect spot to relax after a beach day or enjoy a peaceful afternoon under the Florida sun.

Coral Reef Club 49 Beach Service ~ 2 Chairs & 1 Umbrella (March to October)

Coral Reef Club 49 Enjoy Gulf views even while prepping snacks or pouring drinks—this layout is made for connection and relaxation.

Coral Reef Club 49 Drift into deep sleep on a plush king bed under soft lighting, surrounded by peaceful beachy décor and calming hues.

Coral Reef Club 49 Perfect views of the Gulf

Coral Reef Club 49 Soak in sweeping Gulf views right from your living room!

10 guests 3 bed 2 bath 1,200 sq ft

Panhandle - Destin | Destin

Starting at $329 daily

Tranquility 98 Morning coffee or sunset cocktails, this inviting pool deck is the perfect spot to relax and reconnect outdoors.

Tranquility 98 6 Person Golf Cart!

Tranquility 98 Wake up refreshed — the ensuite bath makes mornings easy and evenings indulgent.

Tranquility 98 Open-concept design keeps everyone connected — enjoy movie nights or casual chats while dinner is being prepared nearby.

Tranquility 98 Cook, dine, and relax together in this open-concept kitchen that flows seamlessly into the living area.

Tranquility 98 Beach Setup is included at the property for guest use. (This is not beach service)

Tranquility 98 Enjoy the convenience of an in-home elevator with access to all three floors — perfect for luggage, groceries, and easy mobility.

Tranquility 98 Work or unwind in this inviting first-floor space featuring a TV, desk, and easy walk-out to your private pool oasis.

14 guests 5 bed 5 bath 3,564 sq ft

Panhandle - Destin | Destin

Starting at $110 daily

Beach Manor 1004 Inviting living room with smart TV, cozy seating, and adjacent dining space—perfect for relaxing after beach days.

Beach Manor 1004 Furnished private balcony with seating for enjoying morning coffee, sunsets, and ocean breezes high above the shoreline.

Beach Manor 1004 Primary suite offering direct access to the private balcony and peaceful views—perfect for morning coffee or evening relaxation.

Beach Manor 1004 Enjoy 1 free adult activity admission daily (value over $500)! Not available for stays 27+ days.

Beach Manor 1004 Cozy dining area with seating for four, open to the living room and balcony for easy meals and relaxed gatherings.

Beach Manor 1004 Bright, remodeled kitchen featuring stainless steel appliances, quartz countertops, and island seating for casual dining.

Beach Manor 1004 Inviting living room with smart TV, cozy seating, and adjacent dining space—perfect for relaxing after beach days.

Beach Manor 1004 Inviting living room with smart TV, cozy seating, and adjacent dining space—perfect for relaxing after beach days.

6 guests 2 bed 2 bath 1,207 sq ft

Panhandle - Miramar Beach | Miramar Beach

Starting at $259 daily

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