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Holiday Vacation Rentals

Hotels (2)

B&Bs / Inns (0)

Specialty Lodging (0)

Vacation Rentals (137)

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Relax at the Sunset Bungalow, Port Richey
Relax at the Sunset Bungalow
    Price: €87 - €97/night €485 - €554/week €1,800 - €2,077/month
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 2
  • Min stay: 2
    • Contact Owner
Lakefront Home on 450 Acre Ski Lake * Tampa Bay FL, Odessa
Lakefront Home on 450 Acre Ski Lake * Tampa Bay FL
    Price: €692 - €1,039/week €2,423/month
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 3
    • Contact Owner
Beach Cottages II Unit 2106 Indian Shores, Fl, Indian Shores
Beach Cottages II Unit 2106 Indian Shores, Fl
    Price: €586 - €1,052/week
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 2
  • Min stay: 7
    • Contact Owner
Waterfront Resort Condo, Indian Shores
No photo provided
    Price: €66 - €100/night €450 - €623/week
  • Bedrooms: 1, sleeps 4
  • Bathrooms: 1
  • Min stay: 6
    • Contact Owner
Luxury Pool Home near Beach, Clearwater
Luxury Pool Home near Beach
    Price: €2,423/week €2,423 - €4,674/month
  • Bedrooms: 6, sleeps 13
  • Bathrooms: 3
    • Contact Owner
Beautiful Gulffront Cottages Sandy Shores/PATIO, Indian Rocks Beach
Beautiful Gulffront Cottages Sandy Shores/PATIO
    Price: €481 - €689/week
  • Bedrooms: 1, sleeps 4
  • Bathrooms: 1
    • Contact Owner
BEACHFRONT PARADISE, Indian Rocks Beach
BEACHFRONT PARADISE
    Price: €831/week
  • Bedrooms: 2, sleeps 7
  • Bathrooms: 2
    • Contact Owner
The Island House in the heart of Downtown Dunedin, Dunedin
The Island House in the heart of Downtown Dunedin
    Price: €62/night €415/week €1,212/month
  • Bedrooms: 3, sleeps 5
  • Bathrooms: 2
    • Contact Owner
2 Heated Pools, Tangerine Dream Cottage, Clearwater
2 Heated Pools, Tangerine Dream Cottage
    Price: €620 - €1,243/week
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 2
  • Min stay: 7
    • Contact Owner
Florida Beach Rental House, Clearwater
Florida Beach Rental House
    Price: €207/night €1,377 - €4,839/week
  • Bedrooms: 10, sleeps 28
  • Bathrooms: 6
    • Contact Owner

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There are no vacation rentals within Holiday, Florida. We broadened your search to include all rentals within 25 miles.

Beach Dreams - Indian Shores Florida, Indian Shores
Beach Dreams - Indian Shores Florida
Contact Owner
4.5 of 5 stars 10 reviews
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Min stay:7
Our beautiful Beach Cottage II unit sits conveniently on the first floor with a direct walkout to the large pool deck, jacuzzi, bbq and BEACH! Indian Shores ...
  • Nightly
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  • Weekly
    €537 - €952
  • Monthly
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Dockside Condos, Clearwater
Dockside Condos
Contact Owner
4.5 of 5 stars 21 reviews
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 10
Bathrooms: 2
Min stay:7
One, Two and Three bedroom condos, featuring granite counter tops in the kitchen and bathrooms along with new stainless steel appliances including a glass top ...
  • Nightly
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  • Weekly
    €505
  • Monthly
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Sea Gate 504, Indian Shores
Sea Gate 504
Contact Manager
4 of 5 stars 3 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
Spectacular views from the huge balcony of this top floor Sea Gate condo! Rental includes unlimited North American long distance and High Speed Internet ...
  • Nightly
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  • Weekly
    €675 - €1,108
  • Monthly
    €2,604 - €3,711
Oceanside - Unit: OC405, Indian Rocks Beach
Oceanside - Unit: OC405
Contact Manager
4.5 of 5 stars 5 reviews
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 6
Bathrooms: 2
Oceanside 405 Indian Rocks Beach 2/2 Gulf Front Deluxe. NEW IN INVENTORY Top floor unit. Stunning gulf front view. Tommy Bahama furnishing with an ...
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Harbor View Grande, Clearwater
Harbor View Grande
Contact Owner
4.5 of 5 stars 7 reviews
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
Here’s the real deal for a truly wonderful vacation rental! Rich wood cabinets and beautiful granite in the kitchen. Cool tile throughout except for ...
  • Nightly
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  • Weekly
    €1,104
  • Monthly
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Crystal Escape, Crystal Beach
Crystal Escape
Contact Manager
Nightly rate from
€165
4.5 of 5 stars 12 reviews
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 18
Bathrooms: 4
Escape to the beach, to the charming Crystal Beach community in Destin, Florida. Private pool , screened-in porch and a short walk to the beach await you ...
  • Nightly
    €165 - €436
  • Weekly
    €1,027 - €2,510
  • Monthly
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Bay Harbor 303, Clearwater
Bay Harbor 303
Contact Manager
4 of 5 stars 2 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 3
Brand New Construction!!! Third floor condo at Bay Harbor of Clearwater Beach! Watch the dolphins & sea turtles from your private balcony! Footsteps away ...
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  • Weekly
    €675 - €1,108
  • Monthly
    €2,604 - €3,711
Sandcastle I - Unit: SI308, Indian Shores
Sandcastle I - Unit: SI308
Contact Manager
4 of 5 stars 3 reviews
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 6
Bathrooms: 2
Description: Sandcastle # 308 Direct Gulf Front Great 2 bedroom 2 bath w/den.Newly upgraded late 2008.Contemporary Decor.Remodeled Handicap Friendly Master ...
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My Indian Shores Family Resort Vacation Condo, Indian Shores
My Indian Shores Family Resort Vacation Condo
Contact Owner
Nightly rate from
€55
4 of 5 stars 1 review
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 7
Bathrooms: 2
Magnificent 2-bedroom/2-bathroom condominium beach vacation rental in resort oceanfront property on Indian Shores Beach on the Gulf of Mexico. Indian Shores ...
  • Nightly
    €55 - €125
  • Weekly
    €389 - €876
  • Monthly
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Cobia Cottage, Crystal Beach
Cobia Cottage
Contact Manager
Nightly rate from
€114
4.5 of 5 stars 10 reviews
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 12
Bathrooms: 3
Visit Destin beaches in this charming cottage in Crystal Beach. With private pool and within walking distance to the beach, it is a great place to stay at ...
  • Nightly
    €114 - €289
  • Weekly
    €684 - €1,672
  • Monthly
    €872 - €1,108
Sweet Destiny, Crystal Beach
Sweet Destiny
Contact Manager
Nightly rate from
€172
4.5 of 5 stars 8 reviews
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 16
Bathrooms: 4
Stay in the Crystal Shores neighborhood in this beach cottage with private pool ! With spacious floor plan, Gourmet Kitchen and Bonus Room with Kitchenette, ...
  • Nightly
    €172 - €523
  • Weekly
    €1,035 - €3,009
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Crystal Dunes #602, Crystal Beach
Crystal Dunes #602
Contact Manager
Nightly rate from
€169
4.5 of 5 stars 2 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 4, sleeps 8
Bathrooms: 4
Journey to the Emerald Coast and enjoy this spacious four bedroom two level penthouse. The views are spectacular from this Destin, Florida accommodation; you ...
  • Nightly
    €169 - €476
  • Weekly
    €1,058 - €2,739
  • Monthly
    €1,451 - €1,520
La Ti Da, Crystal Beach
La Ti Da
Contact Manager
Nightly rate from
€165
4 of 5 stars 6 reviews
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 15
Bathrooms: 6
Stay in the charming beach community of Crystal Beach in Destin. At La Ti Da, enjoy your private pool , separate Cabana and Gulf views from the third floor ...
  • Nightly
    €165 - €436
  • Weekly
    €1,027 - €2,510
  • Monthly
    €872 - €969
Emerald Dunes #505, Crystal Beach
Emerald Dunes #505
Contact Manager
Nightly rate from
€169
4 of 5 stars 1 review
Management: Professional
Property: Condo/Apartment
Bedrooms: 4, sleeps 14
Bathrooms: 4
Soak in the wonderful views from this Destin, Florida vacation accommodation. This unique condo occupies the West end corner of the top two floors of the ...
  • Nightly
    €169 - €476
  • Weekly
    €1,058 - €2,739
  • Monthly
    €1,520
Dunes of Crystal Beach #101, Crystal Beach
Dunes of Crystal Beach #101
Contact Manager
4.5 of 5 stars 8 reviews
Management: Professional
Property: Condo/Apartment
Bedrooms: 5, sleeps 12
Bathrooms: 4
Retreat to the beach and visit with us at five bedroom Dune’s of Crystal Beach #101 . Delight in the large balcony that overlooks the Gulf of Mexico and ...
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  • Weekly
    €1,176 - €3,043
  • Monthly
    €1,662 - €1,731
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns