The Holiday Life

Reviews (53)

The Holiday Life offers upscale vacation and seasonal home rentals in Southwest Florida and the Kentucky Bluegrass Region. Each of our beaut...

The Holiday Life offers upscale vacation and seasonal home rentals in Southwest Florida and the Kentucky Bluegrass Region. Each of our beautifully appointed private properties has something special to offer and comes equipped with the type of amenities and concierge service you’d expect at a fine hotel. Our mission is to represent a collection of destination homes where embracing the holiday life becomes as simple as packing your suitcase and making your way to paradise!

Office located in
Marco Island, Florida, United States
Listed on TripAdvisor since
November 2013
Languages spoken
English
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Rentals from The Holiday Life

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Rentals in: Naples (19), Marco Island (13), Lexington (2)

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1 / 22

CORAL FALLS - Light and Bright Lely Resort Condo

  • 2
  • 4
  • 4 nights min

$95

Details

1 / 22

BONITA COURT - Island Luxury Waterfront 4 Bedroom

  • 4
  • 8
  • 4 nights min

$275

Details

1 / 24

EDGEWATER - Waterfront sunset views, watch the Dolphins play!

  • 3
  • 6
  • 4 nights min

$196

Details

1 / 17

MARLIN COURT - Newly Furnished Coastal Paradise Steps to South Marco Beach!

  • 3
  • 8
  • 4 nights min

$346

Details

1 / 18

CHATEAU VANDERBILT - Waterfront Nautical Theme Luxury Condo

  • 3
  • 5
  • Min stay varies

$118

Details

1 / 18

Sandcastle Villa 1 on Vanderbilt Beach

  • 2
  • 8
  • 4 nights min

$295

Details

1 / 16

MARCO BEACH OCEAN RESORT Suite 506, Private Terrace - Sleeps 4!

  • 1
  • 4
  • Min stay varies

$166

Details

1 / 50

VISTA POINT ESTATE - Naples' Best Waterfront Rental, Local Concierge Service

  • 4
  • 8
  • 30 nights min

$2571

Details

1 / 21

HARBOR LANE BUNGALOW - Modern, Waterfront, Downtown Naples minutes to 5th!

  • 3
  • 8
  • 4 nights min

$376

Details

1 / 24

Amador at Fiddler's Creek

  • 4
  • 8
  • Min stay varies

$130

Details

1 / 16

Mulberry Hill - Modern Downtown Townhouse near Gratz Park!

  • 2
  • 4
  • 3 nights min

$162

Details

1 / 26

MARIANA COURT - Luxurious 5 Bedroom on Wide Water w/ Lots of Amenities!

  • 5
  • 10
  • Min stay varies

$401

Details

1 / 20

ADMIRALTY - Coastal Comfort on a Gulf Access Canal!

  • 3
  • 6
  • 4 nights min

$295

Details

1 / 21

South Seas 3-807 - Best View on the Island!

  • 2
  • 4
  • 7 nights min

$140

Details

1 / 17

Casa Verde - Mid Century Modern Downtown Bungalow

  • 3
  • 10
  • 3 nights min

$263

Details

1 / 27

Varenna at Fiddler's Creek - Gorgeous Lake View, First Floor Coach Home!

  • 3
  • 6
  • Min stay varies

$81

Details

1 / 24

BARFIELD - Modern & Spacious with Big Water Views!

  • 4
  • 8
  • 4 nights min

$396

Details

1 / 23

STARFISH BEACH HOUSE - Waterfront Home in Coveted Seagate Beach Community

  • 3
  • 8
  • Min stay varies

$445

Details

1 / 16

EDGEWATER II - Luxurious 3/3 on Wide Water with Western Exposure!

  • 3
  • 8
  • Min stay varies

$396

Details

1 / 21

GREENLINKS 911 - 3 Bedroom Fairway View Golf Villa

  • 3
  • 8
  • 4 nights min

$115

Details

1 / 19

Greenlinks 1414 - Best View in Lely, Renovated Coastal Golf Villa!

  • 2
  • 4
  • 4 nights min

$201

Details

1 / 26

SPINNAKER BEACH HOUSE - Spacious Coastal Tigertail Home on Water!

  • 4
  • 9
  • 4 nights min

$396

Details

1 / 24

GREENLINKS - Fairway View 2 Bedroom + Den Golf Villa

  • 2
  • 6
  • 4 nights min

$105

Details

1 / 19

CANARY COVE COTTAGE in Olde Naples, Steps to 3rd St S

  • 3
  • 8
  • 4 nights min

$501

Details

1 / 20

FIELDSTONE BEACH HOUSE - 4 Bed, Walking Distance to Beach and Shopping!

  • 4
  • 10
  • 4 nights min

$326

Details