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Holiday Rentals

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age 0-16
550 Results

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Price: high to low

Number of reviews

550 Houses

Waterfront Florida Home w/ Boat Lift & Kayaks!

Holiday house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$201

Responds fast! avg. 27 minutes

Price per night from

$202

2 Bedroom waterfront vacation retreat

Holiday house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 53 minutes

Price per night from

$172

Geodesic Dome

Holiday apartment

1 bedroom / 1 bathroom / sleeps 4

“Ms” Me and my children stayed for 11 days and had the most wonderful vacation!! Thank you Sharon and Ralph...y'all are the best!! We will definitely be returning!!

Price per night from

$166

Charming Holiday Getaway - 6 Miles to Sunset Beach

Holiday house

2 bedrooms / 1 bathroom / sleeps 8

Price per night from

$113

Responds fast! avg. 3 hours 33 minutes

Price per night from

$249

Dolphin Cove Villa

Holiday house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 57 minutes

Price per night from

$722

Holiday Home w/Outdoor Oasis -1 Mile to Beach

Holiday house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$90

Snowbirds' Dream, Minutes from the Beach, Shopping, Nature and Biking Trails

Holiday house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 26 minutes

Price per night from

$194

NEW! Charming Home w/ Patio, 7 Mi to Sunset Beach!

Holiday house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$95

Great rentals within 20 miles that match your search

DESIGNER APARTMENT

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$97

Welcome to the Mar Bay Motel & Suites

Safety Harbor hotel apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$373

single family home one level, all one family homes community

New Port Richey house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 40 minutes

Price per night from

$74

Breathtaking Gulf Front Home-Gulfside Gallery LLC

Tarpon Springs house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$453

Island Estates Clearwater Beach Waterfront Condomimium

Clearwater condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$152

4 Bedroom 2 Bath Bayfront, Pool, Gof, Canoe, More.

Tampa house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$356

Waterfront Paradise in Destination Hudson, FL

Hudson house

2 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$201

TAMPA BAY WATERFRONT CONDO!

Tampa condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$206

3br - Belleair beach vacation rental, 3bd/2bth

Tampa house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$217

Gulfront Condo with spectacular sunsets

Port Richey apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$78

Location/Beautiful townhome in sunny Tampa. Pool/6 MONTHS MINIM. STAY.

Tampa townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$91

Lovely Tropical Sunlit bedroom

Clearwater house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$258

Clearwater, Florida 2 Bedroom Fully Equipped Condo

Clearwater apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Location” Excellent location, close to beach and shopping, very clean unit. Loved that there were beach chairs and lots of towels available. Owners were easy to deal with and very cooperative. I would definitely rent this condo again.

Responds fast! avg. 20 minutes

Price per night from

$82

Enjoy Unlimited Free Golf, Near Top-rated Beaches, Dec. Special!

Palm Harbor house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$149

Acorn Terrace

Safety Harbor apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$137

JUST DROP YOUR BAG'S AND ENJOY YOUR VACATION.

Hudson house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$69

Sensational Condo

Safety Harbor condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$299

The Yellow House

Largo apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$67

Delightful Dunedin - Near to Clearwater Beaches

Dunedin house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 54 minutes

Price per night from

$120

Exclusive Tropical Retreat in Sunny Clearwater Bea

Clearwater house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 33 minutes

Price per night from

$508

Brand New! Welcome to your vacation home

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$112

Villas of Clearwater B1

Clearwater condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$149

Beautiful 4 Bd Pool Home!

New Port Richey house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 54 minutes

Price per night from

$212

Cozy Vacation Home 15 mins from Beaches

Dunedin house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 20 minutes

Price per night from

$140

Clearwater Sugar Beach

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 1

Price per night from

$86

Cozy studio condo with great view on Sand Key beach

Clearwater condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$104

Gulf Front Island Paradise with dock and pool - Special September Rates!

Palm Harbor house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$455

Tommy Bahama Water View Beach Condo

Clearwater condo

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$180

Viewing 38 of 550
rentals in Holiday

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Top Destination reviews

Geodesic Dome
Will and already have recomend to others.

Lots of fun places to see and eat at nearby. Sharon and Ralph made sure we had everything we needed. … see more
Waterfront Florida Home w/ Boat Lift & Kayaks!
Great place to stay

We had a wonderful time. The house was absolutely beautiful! We had no problems. There were so many amenities. Sitting or fishing on the back dock was so relaxing. We would definitely stay here again. … see more
Clearwater Florida area's best kept secret, GULF FRONT 80FT LAP POOL AND WIFI
Nice place to stay!

Beautiful place to enjoy all that Tarpon Springs area has to offer. Place is a good example of old Florida. Lovely pool to enjoy the picturesque view of the river and ocean. Stingrays, manatees and various fish species hang around the dock at varied times. Thank you Dianne for opening your home to us!see more

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