Luxury Florida Vacation Homes

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BW 1 Enjoy the Waterfront Views All Day – Sip your morning coffee or evening wine on the patio while boats glide by and dolphins occasionally pop up in the water

BW 1 Main bedroom with 1 queen sized bed

BW 1 Dining area that can comfortably sit 4 guests.

BW 1 Spacious living room space to bond with the family

BW 1 Enjoy the Waterfront Views All Day – Sip your morning coffee or evening wine on the patio while boats glide by and dolphins occasionally pop up in the water

BW 1 Enjoy the Waterfront Views All Day – Sip your morning coffee or evening wine on the patio while boats glide by and dolphins occasionally pop up in the water

BW 1 Spacious living room space to bond with the family

BW 1 Spacious living room space to bond with the family

2 guests 1 bed 1 bath 789 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

5.0 (5)

Guest rating

Starting at $95 daily

10265 115th Ave N Cozy living room with a huge couch and a smart tv

10265 115th Ave N Spacious dining table to enjoy meals with the family

10265 115th Ave N 5 O'Clock Somewhere is within a short drive to Clearwater Beach!

10265 115th Ave N Bedroom 2 with a queen sized bed

10265 115th Ave N Clearwater Beach, FL. A short drive away from our home!

10265 115th Ave N Bedroom 2 with a queen sized bed

10265 115th Ave N Just a short drive to the beach!

10265 115th Ave N 2nd Living room area with a 3 seater couch and a smart tv.

8 guests 3 bed 1 bath 1,039 sq ft

Gulf Coast - Other | Largo

5.0 (1)

Guest rating

Starting at $199 daily

1021 Mandalay Convenient garage access makes beach days and unpacking easy.

1021 Mandalay Backyard
Unwind outdoors on your private patio, grill dinner, and enjoy the lush tropical surroundings.

1021 Mandalay Living Room
Relax and unwind with a movie night on the smart TV in this open, comfortable gathering space.

1021 Mandalay Enjoy peaceful surroundings away from the busy crowds while still being just minutes from all that Clearwater Beach has to offer.

1021 Mandalay Bedroom 1
Drift off in a serene queen bedroom filled with natural light, soft coastal touches, and relaxing ceiling-fan comfort.

1021 Mandalay Kitchen & Dining
Cook, gather, and connect in the fully equipped kitchen with breakfast nook seating and a dining table for six.

1021 Mandalay Backyard
Unwind outdoors on your private patio, grill dinner, and enjoy the lush tropical surroundings.

1021 Mandalay Sunroom
A cozy sun-filled retreat perfect for morning coffee, work space, or extra sleeping space with a convenient trundle bed.

6 guests 2 bed 2 bath 1,433 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

5.0 (2)

Guest rating

Starting at $218 daily

BW 3 This peaceful retreat offers beautiful water views, coastal comfort, and the chance to spot dolphins and manatees right from the unit.

BW 3 This peaceful retreat offers beautiful water views, coastal comfort, and the chance to spot dolphins and manatees right from the unit.

BW 3 Peaceful bedroom featuring a queen-size bed and a calming coastal feel for restful nights.

BW 3 Cozy waterfront living area with a comfortable couch and Smart TV—perfect for relaxing after a beach day.

BW 3 Private deck with outdoor seating for two—enjoy your morning coffee while watching boats, dolphins, and tranquil bay views.

BW 3 Fully equipped kitchen with oven, stove, refrigerator, and coffee maker—everything you need for easy vacation meals.

BW 3 Cozy waterfront living area with a comfortable couch and Smart TV—perfect for relaxing after a beach day.

BW 3 This peaceful retreat offers beautiful water views, coastal comfort, and the chance to spot dolphins and manatees right from the unit.

2 guests 1 bed 1 bath

Gulf Coast - Clearwater Beach | Clearwater Beach

5.0 (1)

Guest rating

Starting at $131 daily

CR B5 Bright coastal living room with comfortable seating and stunning Intracoastal Waterway views

CR B5 Gorgeous waterfront views!

CR B5 Sparkling community pool at Coral Resort—perfect for cooling off after the beach

CR B5 Just steps from sugar-white sand beaches and the Gulf of Mexico

CR B5 Comfortable bedroom with ample storage and calming beach-inspired décor

CR B5 Relaxing living area overlooking the Intracoastal—perfect for unwinding after the beach

CR B5 Coastal living at its finest in the heart of Clearwater Beach

CR B5 Open-concept living space filled with natural light and serene water vistas

4 guests 1 bed 2 bath

Gulf Coast - Clearwater Beach | Clearwater Beach

5.0 (11)

Guest rating

Starting at $65 daily

18 Heilwood 2 Steps from the sugar white sands of Clearwater Beach!

18 Heilwood 2 • Studio Layout with Cozy Queen Bed – Memory-foam mattress for a great night's sleep and a roomy open layout for relaxing after beach days

18 Heilwood 2 Enjoy your morning coffee with a beachside breeze

18 Heilwood 2 • Full Bathroom – Spacious and updated for comfort and convenience

18 Heilwood 2 • Dining Nook – Perfect for meals, remote work, or planning your next beach adventure

18 Heilwood 2 • Fully Equipped Kitchenette – Includes fridge, microwave, stovetop, coffee maker, and essential cookware

18 Heilwood 2 • Studio Layout with Cozy Queen Bed – Memory-foam mattress for a great night's sleep and a roomy open layout for relaxing after beach days

18 Heilwood 2 • Studio Layout with Cozy Queen Bed – Memory-foam mattress for a great night's sleep and a roomy open layout for relaxing after beach days

2 guests 0 bed 1 bath 320 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

5.0 (11)

Guest rating

Starting at $99 daily

1122 Charles Pool

1122 Charles Located close to the beach!

1122 Charles Spacious Master bedroom with 1 king sized bed, smart tv, ceiling fan

1122 Charles Spacious living room with natural light coming in

4 guests 2 bed 2 bath

Gulf Coast - Other | Clearwater

5.0 (3)

Guest rating

Starting at $159 daily

16333 Gulf Blvd 215

16333 Gulf Blvd 215 SUNNY ORANGE STAYS presents… ☀️ Sunset Corner ➠ 16333 Gulf Blvd 215

16333 Gulf Blvd 215

16333 Gulf Blvd 215

16333 Gulf Blvd 215

16333 Gulf Blvd 215

16333 Gulf Blvd 215

16333 Gulf Blvd 215

4 guests 1 bed 1 bath

Gulf Coast - Other | Redington Beach

Starting at $106 daily

RVH_588M | Magic Views Located in the prestigious Reunion Resort, Magic Views is a spacious 6-bedroom, 6-bathroom villa located on an elevated lot with breathtaking views | Photos updated: May 2024

RVH_588M | Magic Views

RVH_588M | Magic Views

RVH_588M | Magic Views

RVH_588M | Magic Views

RVH_588M | Magic Views

RVH_588M | Magic Views

RVH_588M | Magic Views

12 guests 6 bed 6 bath 4,074 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

Starting at $179 daily

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

DI0103 Centre Court Amore

DI0103 Centre Court Amore

DI0103 Centre Court Amore

DI0103 Centre Court Amore

DI0103 Centre Court Amore

DI0103 Centre Court Amore

DI0103 Centre Court Amore

DI0103 Centre Court Amore

8 guests 3 bed 3 bath 1,590 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

4.8 (11)

Guest rating

Starting at $101 daily

BO0104 Villas South Monaco

BO0104 Villas South Monaco

BO0104 Villas South Monaco

BO0104 Villas South Monaco

BO0104 Villas South Monaco

BO0104 Villas South Monaco

BO0104 Villas South Monaco

BO0104 Villas South Monaco

6 guests 3 bed 3 bath 1,755 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

4.7 (7)

Guest rating

Starting at $126 daily

KGC25240 Beautiful home in Heritage Landing Golf Resort with private pool overlooking golf course. Pool size: 10' x 24' x 5.5'D. Spa size: 6' x 6'

KGC25240 Bright, open living space overlooking the private pool

KGC25240 Bright, open living space

KGC25240 Bright, open living space

KGC25240 Bright, open living space overlooking the private pool

KGC25240 Beautiful, fully-equipped kitchen

KGC25240 Beautiful, fully-equipped kitchen

KGC25240 Beautiful, fully-equipped kitchen

8 guests 3 bed 3 bath 2,449 sq ft

Gulf Coast - Charlotte Harbor | Punta Gorda

Starting at $175 daily

ADT8999 Living Room (Angle)

ADT8999 Living Room
65" Roku TV

ADT8999 Kitchen

ADT8999 Kitchen (Angle)

ADT8999 Breakfast Bar

ADT8999 Dining Room

ADT8999 Dining Room (Angle)

ADT8999 Living Room (Angle 2)

12 guests 6 bed 5 bath 2,750 sq ft

Orlando - Solara Resort | Kissimmee

Starting at $159 daily

RVH_593M | Charming Retreat at Reunion Welcome to Charming Retreat, a stunning 5-bedroom pool home! Photos updated: October 2024

RVH_593M | Charming Retreat at Reunion The kids will delight in splashing around in the evenings, creating joyful memories

RVH_593M | Charming Retreat at Reunion The perfect place for swimming, sunbathing, or hosting outdoor gatherings, this space offers both relaxation and style

RVH_593M | Charming Retreat at Reunion

RVH_593M | Charming Retreat at Reunion Enjoy magical evenings on your extended pool deck featuring the largest infinity pool in the Resort

RVH_593M | Charming Retreat at Reunion Gather in the spacious living room, designed with comfort in mind and ideal for entertaining guests or enjoying family time

RVH_593M | Charming Retreat at Reunion Create cherished memories with your family in this inviting and spacious home

RVH_593M | Charming Retreat at Reunion Experience the freedom of a large open floor plan, ideal for comfortable living and entertaining

10 guests 5 bed 5 bath 3,076 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

Starting at $107 daily

9030SD · Dazzing 9BR/ Pool/Spa/ Free Waterpark (9030SD)

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9030SD · Dazzing 9BR/ Pool/Spa/ Free Waterpark (9030SD) Private Pool and Laydown Chairs

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18 guests 9 bed 5 bath

Orlando - Champions Gate | Davenport

Starting at $173 daily

10 guests 5 bed 6 bath

Orlando - Windsor Island Resort | Davenport

Starting at $158 daily

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8 guests 4 bed 3 bath

Orlando - Champions Gate | Davenport

Starting at $132 daily

440OC · 20% OFF Weekly Stay 4BR Th With Pool(440OC)

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8 guests 4 bed 3 bath

Orlando - Champions Gate | Davenport

Starting at $115 daily

8972CCD · Amazing 6Br Villa Near Disney With Lake View(8972) Listing image 1

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8972CCD · Amazing 6Br Villa Near Disney With Lake View(8972) Dining Area

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8972CCD · Amazing 6Br Villa Near Disney With Lake View(8972) Kitchen Area

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8972CCD · Amazing 6Br Villa Near Disney With Lake View(8972) Kitchen Area

12 guests 6 bed 5 bath

Orlando - Champions Gate | Davenport

Starting at $160 daily

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