Holiday Vacation Rentals, Estates & more


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Areas near Holiday

Great rentals within 20 miles that match your search

1 / 12

Desirable Resort Style Condo in Clearwater

  • 1
  • 3
  • 7 nights min

$62

Details

1 / 13

Spend a great holiday in Florida

  • 2
  • 2
  • 30 nights min

$49

Details

1 / 12

Beautiful waterfront condo in gated resort

  • 2
  • 8
  • 30 nights min

$93

Details

1 / 12

Cozzy townhouse

  • 2
  • 4
  • 90 nights min

$41

Details

1 / 26

Beach Paradise Beach House

  • 3
  • 12
  • Min stay varies

$201

Details

1 / 11

Beautiful 2 bedroom, 2 bath with pool. Waterfront with Gulf access.

  • 2
  • 6
  • 3 nights min

$201

Details

1 / 8

8th Hole Retreat

  • 2
  • 4
  • 30 nights min

$31

Details

1 / 19

Perfect Location, Walk to Everything, All Suites Condo Motel, Full Kitchen

  • 1
  • 4
  • 1 night min

$129

Details

1 / 46

Relaxing Condo~Beautiful Clearwater Beach~Gorgeous Heated Pool~Perfect Vacation!

  • 1
  • 4
  • 7 nights min

$61

Details

1 / 13

LUXURY RETREAT near best GulfCoast Beaches

  • 1
  • 2
  • Min stay varies

$46

Details

1 / 11

Clearwater Beach Waterview Studio

  • Studio
  • 2
  • 3 nights min

$99

Details

1 / 25

(2024) Cozy Villa in Sunny Clearwater, Florida

  • 2
  • 4
  • Min stay varies

$89

Details

1 / 12

A perfect place for a couple, Mango Tango Cottage

  • 1
  • 2
  • Min stay varies

$71

Details

1 / 36

Mins to Airport-Downtown-Busch Gardens-Clearwater!

  • 1
  • 4
  • Min stay varies

$99

Details

1 / 24

Lighthouse Towers Condo on Sandkey Beach

  • 1
  • 4
  • 14 nights min

$79

Details

1 / 4

2 BEDROOM TUSCANY END UNIT CONDO

  • 2
  • 4
  • 7 nights min

$286

Details

1 / 5

Paradise Lakes Resort Cabana Condo

  • 1
  • 3
  • 1 night min

$120

Details

1 / 16

GULF FRONT Private Beach home 4bdrm/4bath

  • 4
  • 10
  • 30 nights min

$857

Details

1 / 4

Five Palms Resort

  • 20
  • 50
  • 1 night min

$3500

Details

1 / 27

Charming Florida Cottage with Waterview

  • 2
  • 4
  • 30 nights min

$68

Details

1 / 22

Sand Key Beach Front Studio

  • Studio
  • 4
  • 30 nights min

$61

Details

1 / 24

Dog-Friendly 2BR, 2BA Clearwater House w/ Pool, 5 Minutes from the Beach

  • 2
  • 6
  • Min stay varies

$176

Details

1 / 21

Great Beach & Intercostal Views - Oceanside

  • 2
  • 4
  • 30 nights min

$121

Details

1 / 18

Beautiful Belle Harbor

  • 3
  • 6
  • 30 nights min

$167

Details

1 / 21

Riverview (Gulf Access)

  • 3
  • 6
  • 1 night min

$95

Details

1 / 25

2BR Holiday House w/Private Pool & Hot Tub!

  • 2
  • 6
  • Min stay varies

$150

Details

1 / 26

Magnificent 4BR Holiday Waterfront House

  • 4
  • 10
  • Min stay varies

$176

Details

1 / 10

Geodesic Dome

  • 1
  • 5
  • 3 nights min

$120

Details

1 / 25

2 Bedroom waterfront vacation retreat

  • 2
  • 7
  • Min stay varies

$150

Details

1 / 30

Dolphin Cove Villa

  • 4
  • 12
  • Min stay varies

$501

Details

1 / 8

Beautiful private home with lake view close to all

  • 2
  • 6
  • Min stay varies

$135

Details

1 / 25

Peace and Tranquility

  • 2
  • 6
  • Min stay varies

$79

Details

1 / 19
1 / 20

Furnished all inclusive, city of Holiday, West Coast FL

  • 2
  • 6
  • 7 nights min

$58

Details

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