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Holiday Rentals

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708 Results

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Price: low to high

Price: high to low

Number of reviews

708 Houses

Waterfront Holiday House w/ Private Pool & Dock!

Holiday house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Price per night from

$248

Florida Waterfront Home w/ Boat Lift & Kayaks!

Holiday house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 4 minutes

Price per night from

$203

Price per night from

$173

2 Bedroom waterfront vacation retreat

Holiday house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 18 minutes

Price per night from

$173

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!!

Responds fast! avg. 3 hours 40 minutes

Price per night from

$148

Charming Holiday Getaway - 6 Miles to Sunset Beach

Holiday house

2 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 4 minutes

Price per night from

$113

Price per night from

$141

Dolphin Cove Villa

Holiday house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$618

Holiday Home w/Outdoor Oasis -1 Mile to Beach

Holiday house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 5 minutes

Price per night from

$80

Price per night from

$119

Waterfront Holiday Home w/ Pvt Fishing Dock!

Holiday house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Price per night from

$96

Pet-Friendly Holiday Home: Patio, Dock+Lake Access

Holiday house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 4 minutes

Price per night from

$92

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

Holiday house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$201

Peace and Tranquility

Holiday condo

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$117

Home away from home

Holiday house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$202

Clearwater Florida area's best kept secret, GULF FRONT 80FT LAP POOL AND WIFI

Holiday house

3 bedrooms / 2 bathrooms / sleeps 7

“Afternoons by the pool” Our family loved this location and will most definitely come back. We enjoyed fishing off the dock, swimming in the pool, and watching the sunsets. Looking at birds and all the fish was so relaxing. There was more than enough room for our family (my wife and I, my parents, and our two daughters) in this cozy house. The location is 5-10 minutes from grocery stores, bait shops, and restaurants. The guided boat tour with Captain Todd is a must. Diane was great to deal with and made us feel right at home. We can’t wait to go back!

Price per night from

$294

Great rentals within 20 miles that match your search

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

Clearwater hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 23 minutes

Price per night from

$152

Clearwater Beach Duplex

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$71

Blessed Address

Dunedin house

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$118

Amazing Sunset over Clearwater Beach

Clearwater condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$94

DESIGNER APARTMENT

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$89

Clean. Modern. PERFECT Location!

Clearwater house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$142

Paradise at Grand Venezia 2BR 2BA 1140 sq ft of comfort

Clearwater condo

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$177

Affordable Luxury Directly On The Gulf Of Mexico.

Clearwater apartment

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 34 minutes

Price per night from

$102

Welcome to the Mar Bay Motel & Suites

Safety Harbor hotel apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$341

Crystal Beach Paradise

Crystal Beach house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$413

"Coral Dive" spacious 2BD 2 BA in Clearwater Florida #1 beach

Clearwater apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$130

Luxurious, Family Beach Home w/Rooftop Terrace

Clearwater house

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$448

ENJOY FLORIDA

New Port Richey house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$95

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

$68

The ocean fixes everything

Palm Harbor house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$195

Aqualea at Hyatt Regency, Clearwater Beach FL

Clearwater apartment

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$201

Newly Renovated 2 Bedroom Condo in Paradise Lakes Nudist Resort

Land O Lakes condo

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$178

The Snuggle Inn

Clearwater house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$106

Cozy Vacation Home 15 mins from Beaches

Dunedin house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 18 minutes

Price per night from

$142

Exclusive Quiet Beach Cottage - Monthly rental

Clearwater cottage

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$237

Delightful Waterfront Condo with Boatslip

Palm Harbor condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 9 minutes

Price per night from

$136

The 'O Place" in New Port Richey, FL

New Port Richey house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$141

Viewing 38 of 708
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
Florida Waterfront 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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