Luxury Florida Vacation Homes

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RD812M Fairway Tropic Oasis

RD812M Fairway Tropic Oasis

RD812M Fairway Tropic Oasis

RD812M Fairway Tropic Oasis

RD812M Fairway Tropic Oasis

RD812M Fairway Tropic Oasis

RD812M Fairway Tropic Oasis

RD812M Fairway Tropic Oasis

25 guests 10 bed 10 bath 9,553 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

5.0 (3)

Guest rating

Starting at $1,608 daily

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

12 guests 6 bed 4 bath 2,812 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Recommended Rental Flex30

Starting at $199 daily

RVH_002M | The Mansion at Reunion Explore The Mansion at Reunion, where grand architecture, private entertainment spaces, and luxurious poolside living come together for an exceptional group getaway.

RVH_002M | The Mansion at Reunion Spend your evenings beside the illuminated private pool and spa, surrounded by elegant outdoor living spaces and a beautiful twilight atmosphere.

RVH_002M | The Mansion at Reunion Admire the estate's impressive entrance, symmetrical design, and elegant architectural details that create a striking first impression.

RVH_002M | The Mansion at Reunion Warm architectural lighting brings the estate's grand entrance to life, creating a welcoming atmosphere as evening settles over Reunion Resort.

RVH_002M | The Mansion at Reunion Enjoy a spectacular poolside experience beneath the expansive screened enclosure, complete with an oversized entertainment screen that brings your favorite sporting events and movie nights to life.

RVH_002M | The Mansion at Reunion Admire the impressive scale and elegant architecture of The Mansion at Reunion, a magnificent private estate surrounded by lush greenery and designed for exceptional group getaways.

RVH_002M | The Mansion at Reunion Make the most of sunny Florida afternoons in your private screened-in pool, featuring in-water loungers, a basketball hoop, and inviting spaces for the whole family to enjoy.

RVH_002M | The Mansion at Reunion Watch the Florida sky transform into brilliant shades of orange and gold as the estate's illuminated outdoor living spaces create a beautiful setting for an evening of relaxation.

24 guests 11 bed 10 bath 12,612 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership Recommended Rental

Starting at $1,436 daily

RVH_470M | The Kingdom at Reunion Welcome to The Kingdom at Reunion! A 12 bedroom, 12.5 bathroom home located in prestigious Reunion Resort.

RVH_470M | The Kingdom at Reunion

RVH_470M | The Kingdom at Reunion

RVH_470M | The Kingdom at Reunion

RVH_470M | The Kingdom at Reunion

RVH_470M | The Kingdom at Reunion

RVH_470M | The Kingdom at Reunion

RVH_470M | The Kingdom at Reunion

32 guests 12 bed 13 bath 12,987 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership Recommended Rental

Starting at $1,346 daily

RVH_527M | The Grand Orlando Welcome to The Grand Orlando, a luxurious 8 bedroom, 11 bath home within the prestigious Bear's Den Club at Reunion Resort

RVH_527M | The Grand Orlando

RVH_527M | The Grand Orlando Infinity edge spa, ledge loungers, and inflatable an unicorn, what else on vacation do you need?

RVH_527M | The Grand Orlando Complete your evening while relaxing in privacy in your own paradise

RVH_527M | The Grand Orlando

RVH_527M | The Grand Orlando Spend your days lounging by this incredible custom built pool with private location

RVH_527M | The Grand Orlando Disclaimer: Firepit(s) not allowed for guest use, homeowner use only.

RVH_527M | The Grand Orlando Enjoy the gorgeous outdoor living space, complete with a summer kitchen, wet bar and plenty of comfortable outdoor seating

21 guests 8 bed 11 bath 7,445 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

Starting at $1,479 daily

Palm Villa 1009

Palm Villa 1009

Palm Villa 1009

Palm Villa 1009

Palm Villa 1009

Palm Villa 1009

Palm Villa 1009

Palm Villa 1009

8 guests 4 bed 4 bath 3,500 sq ft

Gulf Coast - Cape Coral | Cape Coral

Starting at $308 daily

AA15432 Beautiful South Gulf Cove home with private pool, hot tub, and canal access

AA15432 Outdoor dining on the lanai overlooking the sparkling pool & canal

AA15432 Relax on the comfortable sofas in the living room, overlooking the pool and canal
Living Room TV 65'

AA15432 Primary bedroom with king bed, ensuite and lanai access

AA15432 Beautiful South Gulf Cove home with private pool, hot tub, and canal access (Boat lift not available)

AA15432 Formal living room & foyer

AA15432 Formal living room

AA15432 Dining room overlooking pool

11 guests 4 bed 3 bath 2,700 sq ft

Gulf Coast - Charlotte Harbor | Port Charlotte

Starting at $356 daily

620 Bayway Unit 1 Rooftop Terrace – Your private observation deck for sunsets, fireworks, and stargazing.

620 Bayway Unit 1 Boasting 2,400 sq. ft. of interior elegance and a spectacular private rooftop terrace, this end-unit offers panoramic views of the Intercoastal Waterway and frequent dolphin sightings.

620 Bayway Unit 1 Heated Community Pool – A refreshing spot to cool off, shared with only 5 other units.

620 Bayway Unit 1

620 Bayway Unit 1 Spacious Layout – Spread out over three floors with high ceilings and stylish design (Note: No Elevator).

620 Bayway Unit 1 Master bedroom suite with King size bed, smart tv, additional seating and spiral staircase to rooftop deck

620 Bayway Unit 1 Experience elevated coastal living at this sprawling 4-bedroom waterfront beauty.

620 Bayway Unit 1 Private rooftop deck with stunning intracoastal views

9 guests 4 bed 3 bath 2,269 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

4.9 (13)

Guest rating

Starting at $430 daily

2008 20th Ave Parkway Waterfront Living – Located directly on a peaceful intercoastal waterway with stunning views.

2008 20th Ave Parkway Waterfront Living – Located directly on a peaceful intercoastal waterway with stunning views.

2008 20th Ave Parkway Enjoy direct access to the waterfront pool deck from our master bedroom. This room has a king sized bed, smart tv, ceiling fan and ensuite bathroom.

2008 20th Ave Parkway Enjoy meals at the indoor dining table or take it outside for al fresco dining by the water.

2008 20th Ave Parkway Waterfront Living – Located directly on a peaceful intercoastal waterway with stunning views.

2008 20th Ave Parkway Updated and fully equipped with premium appliances, a coffee maker (Keurig & Standard). Plenty of counter space for cooking which also doubles as a breakfast bar.

2008 20th Ave Parkway Bright, spacious and cozy living room area with a huge couch where you can enjoy watching your favorite shows, and spending time with the family

2008 20th Ave Parkway Enjoy meals at the indoor dining table or take it outside for al fresco dining by the water.

6 guests 2 bed 2 bath 1,800 sq ft

Gulf Coast - Indian Rocks Beach | Indian Rocks Beach

5.0 (28)

Guest rating

Starting at $363 daily

Villa Grand Paradise

Villa Grand Paradise

Villa Grand Paradise

Villa Grand Paradise

Villa Grand Paradise

Villa Grand Paradise

Villa Grand Paradise

Villa Grand Paradise

12 guests 6 bed 6 bath 3,245 sq ft

Gulf Coast - Cape Coral | Cape Coral

Starting at $308 daily

Villa Grand Bay Royale

Villa Grand Bay Royale

Villa Grand Bay Royale

Villa Grand Bay Royale

Villa Grand Bay Royale

Villa Grand Bay Royale

Villa Grand Bay Royale

Villa Grand Bay Royale

8 guests 4 bed 3 bath 2,484 sq ft

Gulf Coast - Cape Coral | Cape Coral

Starting at $420 daily

Palm Island Life - 208 Stretch out on poolside loungers with a good book, a cold drink, and the sound of swaying palms all around.

Palm Island Life - 208 Soft lights shimmer on the water—magical evenings begin here.

Palm Island Life - 208 Water reflections and golden skies—your nightly show.

Palm Island Life - 208 Explore the canal in your kayak.

Palm Island Life - 208 Tucked on a peaceful canal in Palm Island, with lush greenery and water views in every direction.

Palm Island Life - 208 Circular drive, tropical landscaping, and an elegant canal-front vibe set the tone.

Palm Island Life - 208 Arrive to a circular driveway, lush tropical landscaping, and a private courtyard that sets the tone for your stay.

Palm Island Life - 208 Tile floors and natural light welcome you as you enter the home.

9 guests 3 bed 2 bath 2,287 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $290 daily

Lido Harbour South - 205 Easy flow from living to restful retreat—where ocean views meet cozy comfort just steps away.

Lido Harbour South - 205

Lido Harbour South - 205 With sunset hues, the pool becomes your serene retreat—perfect for golden hour reflections.

Lido Harbour South - 205 You're just two floors above the sand, perfectly perched to catch every golden sunset and sea breeze.

Lido Harbour South - 205 This is it—your beachfront sanctuary, where sunrise strolls and sunset toasts are your new daily rituals.

Lido Harbour South - 205 Open the door, and step straight into vacation—light-filled, cool, and welcoming.

Lido Harbour South - 205 Quartz countertops to slice fruit for breakfast or mix cocktails for sunset hour.

Lido Harbour South - 205 Gather, sip, and savor in a kitchen made for vacation living—bright, modern, and just steps from sunset dinners on the lanai.

4 guests 1 bed 2 bath 1,172 sq ft

Gulf Coast - Other | Lido Key

Starting at $303 daily

The Banyan Retreat - 26 You'll sink into island-time by the screened, heated pool as canal breezes drift by.

The Banyan Retreat - 26 From above, take in the full layout of the home, shimmering canal waters, and your private dock ready for sun-soaked afternoons.

The Banyan Retreat - 26 Soar above the property and see how close you to the sparkling waters of Lido Beach.

The Banyan Retreat - 26 Relax in the warm glow of the sunset as the sleek Malm fireplace anchors the cozy, beach-inspired living space.

The Banyan Retreat - 26 Dinner with gentle water reflections and soft wind, this canal-side dining sets the tone for real connection.

The Banyan Retreat - 26 Feel the hammock sway, and watch the light dance on the canal. This is your downtime ritual.

The Banyan Retreat - 26 Step onto the private dock, and spot manatees or dolphins passing in the canal.

The Banyan Retreat - 26

8 guests 3 bed 3 bath 1,640 sq ft

Gulf Coast - Other | Lido Key

Starting at $202 daily

SAN3353 Beautiful, bright, open living space. Living room features ample seating, shuffleboard table, electric fireplace, lanai access, and huge 84-inch Smart TV

SAN3353 Gorgeous 4 bedroom, 3 bathroom waterfront home with private pool in Punta Gorda, FL

SAN3353 Gorgeous outdoor living space overlooking the sparkling private pool and canal beyond. Great for entertaining. This space features an outdoor kitchen, ample seating, grill, dining table that seats 8, and 50-inch Smart TV

SAN3353 Gorgeous, fully-equipped kitchen over looking the living room and dining areas

SAN3353 Guest bedroom 1 with king bed 65-inch Smart TV, and fabulous water view

SAN3353 Gorgeous 4 bedroom, 3 bathroom waterfront home with private pool in Punta Gorda, FL

SAN3353 Welcoming foyer

SAN3353 Beautiful, bright, open living space. Living room features ample seating, shuffleboard table, electric fireplace, lanai access, and huge 84-inch Smart TV

8 guests 4 bed 3 bath 2,472 sq ft

Gulf Coast - Charlotte Harbor | Punta Gorda

Starting at $350 daily

RVH_1000M | The One at Reunion Vacation in luxury in this 12 bed, 13,687 sq. ft., 1 acre lot, south facing screened-in pool with theater room, 3 games rooms, & gym

RVH_1000M | The One at Reunion Swim-up bar in pool seating

RVH_1000M | The One at Reunion The huge oversized deck features plenty of seating for everyone and complete privacy

RVH_1000M | The One at Reunion

RVH_1000M | The One at Reunion

RVH_1000M | The One at Reunion Welcome to The One at Reunion! 360 privacy on lot size of 1 acre, situated in behind of 10 acres of the private nature reserve

RVH_1000M | The One at Reunion Rare screened-in screen to keep bugs and debris away, complete privacy and sunny south facing

RVH_1000M | The One at Reunion Sun shelf perfect for children to play

32 guests 12 bed 12 bath 13,687 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership Recommended Rental

Starting at $1,436 daily

QJ062N Imagination at Bear's Den

QJ062N Imagination at Bear's Den

QJ062N Imagination at Bear's Den

QJ062N Imagination at Bear's Den

QJ062N Imagination at Bear's Den

QJ062N Imagination at Bear's Den

QJ062N Imagination at Bear's Den

QJ062N Imagination at Bear's Den

22 guests 8 bed 8 bath 7,142 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

4.6 (10)

Guest rating

Starting at $1,508 daily

QJ068N Enchantment at Bear's Den

QJ068N Enchantment at Bear's Den

QJ068N Enchantment at Bear's Den

QJ068N Enchantment at Bear's Den

QJ068N Enchantment at Bear's Den

QJ068N Enchantment at Bear's Den

QJ068N Enchantment at Bear's Den

QJ068N Enchantment at Bear's Den

18 guests 8 bed 8 bath 7,142 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

5.0 (5)

Guest rating

Starting at $704 daily

RVH_005M | The M Mansion at Reunion

RVH_005M | The M Mansion at Reunion

RVH_005M | The M Mansion at Reunion

RVH_005M | The M Mansion at Reunion

RVH_005M | The M Mansion at Reunion

RVH_005M | The M Mansion at Reunion

RVH_005M | The M Mansion at Reunion

RVH_005M | The M Mansion at Reunion

35 guests 14 bed 12 bath 14,021 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

Starting at $1,695 daily

VP_1832AR Veranda Dream

VP_1832AR Veranda Dream

VP_1832AR Veranda Dream

VP_1832AR Veranda Dream

VP_1832AR Veranda Dream

VP_1832AR Veranda Dream

VP_1832AR Veranda Dream

VP_1832AR Veranda Dream

25 guests 12 bed 12 bath 4,762 sq ft

Orlando - Veranda Palms | Kissimmee

Flex30

Starting at $245 daily

QJ942N Tranquility at Bear's Den

QJ942N Tranquility at Bear's Den

QJ942N Tranquility at Bear's Den

QJ942N Tranquility at Bear's Den

QJ942N Tranquility at Bear's Den

QJ942N Tranquility at Bear's Den

QJ942N Tranquility at Bear's Den

QJ942N Tranquility at Bear's Den

19 guests 8 bed 7 bath 5,720 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

4.7 (7)

Guest rating

Starting at $704 daily

NM391L Legends Coastal Sanctuary

NM391L Legends Coastal Sanctuary

NM391L Legends Coastal Sanctuary

NM391L Legends Coastal Sanctuary

NM391L Legends Coastal Sanctuary

NM391L Legends Coastal Sanctuary

NM391L Legends Coastal Sanctuary

NM391L Legends Coastal Sanctuary

28 guests 10 bed 12 bath 6,451 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

4.4 (5)

Guest rating

Starting at $704 daily

RVH_345M | The Atlantis at Reunion Welcome to The Atlantis at Reunion, a luxury 12 bed villa with home theater, fitness rooms and purpose-built kids bedrooms

RVH_345M | The Atlantis at Reunion

RVH_345M | The Atlantis at Reunion Everyone in your party will love the pool at any time

RVH_345M | The Atlantis at Reunion

RVH_345M | The Atlantis at Reunion

RVH_345M | The Atlantis at Reunion

RVH_345M | The Atlantis at Reunion

RVH_345M | The Atlantis at Reunion

33 guests 12 bed 13 bath 11,500 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

Starting at $1,165 daily

RVH_1094ER Muirfield Allure

RVH_1094ER Muirfield Allure

RVH_1094ER Muirfield Allure

RVH_1094ER Muirfield Allure

RVH_1094ER Muirfield Allure

RVH_1094ER Muirfield Allure

RVH_1094ER Muirfield Allure

RVH_1094ER Muirfield Allure

12 guests 5 bed 6 bath 5,044 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership Recommended Rental Flex30

5.0 (11)

Guest rating

Starting at $395 daily

RVH_207M | The White House at Reunion Welcome to The White House at Reunion Resort

RVH_207M | The White House at Reunion Enjoy an evening swim in the private 50 ft x 30 ft. infinity pool

RVH_207M | The White House at Reunion

RVH_207M | The White House at Reunion Sunny south facing location, take a morning lap or simply swim all day in your large private pool and spa

RVH_207M | The White House at Reunion Sharpen your mini golf skills on the putting green

RVH_207M | The White House at Reunion Keep up on your favorite sports team while enjoying the great outdoors

RVH_207M | The White House at Reunion The privacy of this home is one-of-a-kind with simply nature surrounding your outdoor entertainment area and pool deck

RVH_207M | The White House at Reunion

24 guests 10 bed 11 bath 13,982 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

Starting at $1,255 daily

RVH_610M | Epic Mansion at Reunion Welcome to Epic Mansion at Reunion

RVH_610M | Epic Mansion at Reunion

RVH_610M | Epic Mansion at Reunion

RVH_610M | Epic Mansion at Reunion

RVH_610M | Epic Mansion at Reunion

RVH_610M | Epic Mansion at Reunion

RVH_610M | Epic Mansion at Reunion

RVH_610M | Epic Mansion at Reunion

19 guests 7 bed 8 bath 5,154 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

Starting at $419 daily

RVH_331M | Modern Estate Welcome to the Modern Estate, a luxury 10 bed villa in Reunion

RVH_331M | Modern Estate Come home from a day of enjoying the Orlando attractions and relax in your pool and spa

RVH_331M | Modern Estate The whole family will love nighttime at the private pool

RVH_331M | Modern Estate A perfect crystal blue pool awaits you on your vacation at the Modern Estates

RVH_331M | Modern Estate This gorgeous luxury villa is located in Reunion Resort

RVH_331M | Modern Estate Swim in your private pool with a gorgeous view

RVH_331M | Modern Estate Relax in the pool and spillover spa

RVH_331M | Modern Estate

26 guests 10 bed 10 bath 8,400 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

Starting at $599 daily

RVH_355M | Muirfield Nook Muirfield Nook is a gorgeous 11 bedroom vacation home located in Reunion Resort

RVH_355M | Muirfield Nook

RVH_355M | Muirfield Nook

RVH_355M | Muirfield Nook Have a fun throughout the day by the pool area

RVH_355M | Muirfield Nook

RVH_355M | Muirfield Nook The pool also features a grotto sitting are

RVH_355M | Muirfield Nook Dine alfresco with a meal from the barbecue

RVH_355M | Muirfield Nook

24 guests 11 bed 11 bath 7,901 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

Starting at $985 daily

RVH_370M | Magic Villa at Reunion Welcome to The Magic Villa at Reunion, a 9 bed villa with private pool, lazy river, secret playroom, and custom kids bedrooms | Photos updated: March 2019

RVH_370M | Magic Villa at Reunion Indulge in this luxurious 9 bedroom villa on your next vacation

RVH_370M | Magic Villa at Reunion Experience all this luxurious villa offers

RVH_370M | Magic Villa at Reunion Float down the lazy river

RVH_370M | Magic Villa at Reunion Disclaimer: Firepit(s) not allowed for guest use, homeowner use only.

RVH_370M | Magic Villa at Reunion Enjoy family meals in the beautiful dining table can seat 16

RVH_370M | Magic Villa at Reunion Enjoy your evening by the pool area

RVH_370M | Magic Villa at Reunion Your own private pool with spillover spa and lazy river

24 guests 9 bed 10 bath 6,838 sq ft

Orlando - Reunion Resort | Kissimmee

Reunion Membership

Starting at $649 daily

WH_608BR The Gem Villa

WH_608BR The Gem Villa

WH_608BR The Gem Villa

WH_608BR The Gem Villa

WH_608BR The Gem Villa

WH_608BR The Gem Villa

WH_608BR The Gem Villa

WH_608BR The Gem Villa

14 guests 5 bed 5 bath 2,297 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Recommended Rental Flex30

5.0 (1)

Guest rating

Starting at $209 daily

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