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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Holiday and around

Luxury waterfront townhome, 5 min to beach, pool, boat slip & rooftop deck!
Outdoor dining

Luxury waterfront townhome, 5 min to beach, pool, boat slip & rooftop deck!

10.0 out of 10, Exceptional, (69)
"We had so much fun at this beautiful home and wish we were still there!"
Luxury waterfront townhome, 5 min to beach, pool, boat slip & rooftop deck!
Breezy ‘White Sands House’ Steps to Gulf Shore!
Fridge, microwave, stovetop, dishwasher

Breezy ‘White Sands House’ Steps to Gulf Shore!

9.6 out of 10, Exceptional, (103)
"Great access to the beach, parking on the property, and plenty of space to relax and hang out. "
Breezy ‘White Sands House’ Steps to Gulf Shore!
1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa
On the beach, sun-loungers, beach towels

1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa

10.0 out of 10, Exceptional, (272)
"This property is amazing, and we would absolutely stay here again!"
1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa
Heated Pool | 2BD 2BA | Home near Beaches
Fridge, microwave, oven, stovetop

Heated Pool | 2BD 2BA | Home near Beaches

9.8 out of 10, Exceptional, (24)
"We enjoyed our stay! The location was great—close to the beach yet perfect for exploring Clearwater beyond the shore. The updated home is well-suited for families, friends, or any group, and the pool is a fantastic bonus."
Heated Pool | 2BD 2BA | Home near Beaches
*Pool* 8.5 miles to Honeymoon Island. 4 bdr
Sun-loungers, beach towels

*Pool* 8.5 miles to Honeymoon Island. 4 bdr

10.0 out of 10, Exceptional, (42)
"Loved the area and comfortable accommodations. "
*Pool* 8.5 miles to Honeymoon Island. 4 bdr
Charming Clean Studio in Downtown Clearwater
Exterior

Charming Clean Studio in Downtown Clearwater

9.6 out of 10, Exceptional, (14)
"Everything was as advertised. Great location for beach in clearwater and tampa."
The price is €131
includes taxes & fees
15 Aug - 16 Aug
Charming Clean Studio in Downtown Clearwater
Spacious Tampa Haven: Games / Pool / 7-15 min From Everything
Smart TV, fireplace, video games

Spacious Tampa Haven: Games / Pool / 7-15 min From Everything

9.4 out of 10, Exceptional, (13)
"Beautiful home, the Owner was very friendly and accommodating to our needs. Responded to emails in a timely manner. Next time I'm in Tampa I would love to stay here again."
Spacious Tampa Haven: Games / Pool / 7-15 min From Everything
Clearwater Beach House - Right On The Beach
On the beach

Clearwater Beach House - Right On The Beach

9.6 out of 10, Exceptional, (114)
"Convenient to Beach and local restaurants"
The price is €409
includes taxes & fees
15 Aug - 16 Aug
Clearwater Beach House - Right On The Beach
Paradise Privacy Cottage
Outdoor dining

Paradise Privacy Cottage

9.2 out of 10, Wonderful, (21)
"This was perfect for my daughter and I, located in a cute neighborhood and close to many things. It was very clean and allowed for privacy, definitely felt like home away from home and would highly recommend. "
The price is €126
includes taxes & fees
17 Aug - 18 Aug
Paradise Privacy Cottage
New Luxury House Pool. Just 14 Minutes From the Airport
Interior

New Luxury House Pool. Just 14 Minutes From the Airport

9.4 out of 10, Exceptional, (19)
"Recommended place in Tampa"
New Luxury House Pool. Just 14 Minutes From the Airport
Private Oasis Retreat Heated Pool Hot Tub Beaches
A heated pool

Private Oasis Retreat Heated Pool Hot Tub Beaches

10.0 out of 10, Exceptional, (18)
"We enjoyed this place very much. We spent a lot of time around the pool very nice area."
Private Oasis Retreat Heated Pool Hot Tub Beaches
Beautiful Remodeled House - Outdoor Pool & screened Florida Room
Property grounds

Beautiful Remodeled House - Outdoor Pool & screened Florida Room

9.8 out of 10, Exceptional, (60)
"This house went beyond our expectations. Very clean, spaciousand had anything and everyrhing you need"
Beautiful Remodeled House - Outdoor Pool & screened Florida Room
Cozy home, rural setting, near Gulf Beaches
Fridge, microwave, oven, stovetop

Cozy home, rural setting, near Gulf Beaches

10.0 out of 10, Exceptional, (114)
"Very nice quiet place! We enjoyed our stay. Sherri the owner is very sweet and accommodating.Thanks bunches! "
Cozy home, rural setting, near Gulf Beaches
Heated Pool, 3-bedroom Home with WiFi in Clearwater
Living area

Heated Pool, 3-bedroom Home with WiFi in Clearwater

9.0 out of 10, Wonderful, (2)
"We had an awesome time at this beautiful home"
Heated Pool, 3-bedroom Home with WiFi in Clearwater
Quiet Bungalow Just Minutes To Clearwater/Honeymoom Beaches/Dunedin/Blue Jays
Outdoor dining

Quiet Bungalow Just Minutes To Clearwater/Honeymoom Beaches/Dunedin/Blue Jays

9.2 out of 10, Wonderful, (81)
"Great property. My kiddos loved it. Location is key. Close enough to all the tourist areas but far enough away to avoid all the tourists. Quiet street. "
Quiet Bungalow Just Minutes To Clearwater/Honeymoom Beaches/Dunedin/Blue Jays
Ocean Sands | Beachfront | Private Pool
Pool

Ocean Sands | Beachfront | Private Pool

9.8 out of 10, Exceptional, (85)
"We had a fantastic time here. The home had plenty of room for all 9 of us. Was amazing to be right on the beach. The views from the house and pool were incredible. A family vacation we will never forget. Our grandson also found 14 shark teeth on our walks along the veach"
Ocean Sands | Beachfront | Private Pool
14 Guests · Large HEATED Pool · Tropical Backyard+BBQ · GYM · Beach: 3 miles
A heated pool

14 Guests · Large HEATED Pool · Tropical Backyard+BBQ · GYM · Beach: 3 miles

9.8 out of 10, Exceptional, (30)
"Amazing place for a family to stay for vacation! Close to the beach and airport. Recommend them to anyone with a big family for vacation and the pool was a plus also! "
The price is €525
includes taxes & fees
18 Aug - 19 Aug
14 Guests · Large HEATED Pool · Tropical Backyard+BBQ · GYM · Beach: 3 miles
*New Listing* Pelican Creek-Heated Pool-Game Room
Private kitchen

*New Listing* Pelican Creek-Heated Pool-Game Room

9.0 out of 10, Wonderful, (10)
"Stay was great overall. Few repairs needed here and there but that’s to be expected. Host Matthew was a gem and responded quickly whenever I had a question. Would definitely stay again!"
*New Listing* Pelican Creek-Heated Pool-Game Room
Modern Heater pool house tampa. Close to the park and zoo
3 bedrooms, desk, iron/ironing board, travel cot

Modern Heater pool house tampa. Close to the park and zoo

9.8 out of 10, Exceptional, (119)
"Great place for our short one night stay"
The price is €335
includes taxes & fees
15 Aug - 16 Aug
Modern Heater pool house tampa. Close to the park and zoo
House near Tarpon Springs Beaches and Weeki Wachee Springs
Outdoor spa tub

House near Tarpon Springs Beaches and Weeki Wachee Springs

9.8 out of 10, Exceptional, (16)
"We really loved the place it was perfect and the host were very nice and friendly can’t say enough about the place.Will definitely stay here again "
House near Tarpon Springs Beaches and Weeki Wachee Springs
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Holiday Hotel Reviews

Shephard's Beach Resort

Shephard's Beach Resort

10/10 Excellent
"Great hotel, close to everything. The beds slept incredible. Regina at the front desk was a huge help. Excellent recommendations on places to eat and things to do. "
Jeremy 1-night trip
Posted 10 hours ago
Shephard's Beach Resort