Vacation rentals in Holiday

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Top-rated vacation rentals in Holiday

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Guest favourite

Home in Holiday

4.96 out of 5 average rating, 186 reviews

King Bed Ensuite+Queen 2/2/1—2 Living Spaces+4TVs

Step through the cheery door into your 2BD/2BA mid-century oasis. This home provides an elegant, yet comfortable vibe while featuring lavish amenities including 4 Smart TVs, a fully equipped kitchen, 2 living spaces, a dedicated workspace, a master ensuite, luxury mattresses, private patio, garage parking, a washer & dryer. Enjoy all the comforts while being minutes to grocery stores, restaurants, Tarpon Springs/Sponge Docks(4.9mi) Anclote Beach(4.8mi) Honeymoon Island State Park(16.2mi) & more!

Sep. 10 – 17

$206 CAD per night

Guest favourite

Bungalow in Holiday

4.95 out of 5 average rating, 152 reviews

COZY LAKE RETREAT NEAR BEACHES

The house was just renovated and designed specifically to be a home away from home vacation spot. It's fully furnished with all new furniture, kitchen fully equipped, and other necessary things the guests will need during their stay. It's located on cul de sack with no passing traffic. The back yard has lake access with dock and space to entertain. There is a large 3 person canoe, a paddle boat as well as fishing poles for you to use. Only a few miles away from Tourist attractions and Beach.

Jul. 21 – 28

$202 CAD per night

Guest favourite

Guest suite in Tarpon Springs

4.95 out of 5 average rating, 107 reviews

Private suite in heart of Tarpon Springs!

House centrally located in a safe, residential area. Enjoy a clean, cozy & comfortable private suite with private entrance! Next to Downtown Tarpon, Tarpon Springs Sponge Docks, Sunset Beach, Safety Harbor, and many other attractions. Less than 5 minutes from the beach! Enjoy fast wifi, cable, and a cozy queen bed! Full kitchen. During your stay you’ll have access to bicycles, plenty of beach towels, hats, beach toys. Beach chairs, chairs umbrellas, small cooler and a variety of sunscreens

Jul. 11 – 18

$176 CAD per night

Guest favourite

Cottage in Tarpon Springs

4.99 out of 5 average rating, 136 reviews

Cooper Cottage: Cozy, Convenient and Comfortable

Cooper Cottage is for cyclists, boaters, beach goers or those who just want to relax! The Cottage is the front half of a duplex in downtown Tarpon with all the amenities including bikes and beach gear! Walk/bike to Restaurants, Churches, Museums and Parks in under 12 minutes or drive to Fred Howard Beach or Sunset Beach in 7 minutes! Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue.

Jan. 4 – 11

$254 CAD per night

Superhost

Home in Holiday

4.8 out of 5 average rating, 145 reviews

Cozy Darlington/Close to Beaches

Our beautiful Florida style house is centrally located in Holiday and short distances to the world famous Sponge docks, the historic Greek district of Tarpon Springs, restaurants, the beach, amazing springs where you can kayak/paddle board. Close to Anclote River and Fred Howard Park. The perfect place for couples, solo adventurers, and families. Popular with kite boarders, kayakers, boaters, cyclists, or those who just love to relax. Beach chairs are in the garage and towels in the closet.

May 4 – 11

$211 CAD per night

Superhost

Home in Holiday

4.9 out of 5 average rating, 105 reviews

Fun, Spacious and Modern Waterfront Pool Home

This waterfront pool home is the perfect place to relax and enjoy the Florida lifestyle! The entire home was completely updated in 2020 with a mid century modern style. Everything is new from the floor to the ceiling! Enjoy the gorgeous sunsets from the pool or jacuzzi. Kayak the canals and lakes filled with manatees, sting rays, fish and sometimes even Dolphins! Throw a line in off the dock and catch dinner, or release and catch again. 3 Bedrooms and 3 Bathrooms sleeps 6 comfortably.

Mar. 30 – Apr. 6

$423 CAD per night

Guest favourite

Home in Tarpon Springs

4.93 out of 5 average rating, 103 reviews

Our Gemini Place: Comfort & Charm in Old Tarpon

Welcome to Gemini Place, a cool, quiet 2/2 filled with an easy charm. This solid 1,100- sq. ft house is in the heart of old Tarpon and is a perfect, simple escape for a few days, a few weeks or longer. The north-facing house sits on a one-way brick street and is an easy walk to everything in this quaint, Greek-flavored town. We are close to some of the best beaches in the U.S. We're pet friendly but do have restrictions and a fee that is determined by several factors. Please inquire.

Jul. 19 – 26

$226 CAD per night

Guest favourite

Apartment in Port Richey

4.84 out of 5 average rating, 122 reviews

Port Richey, Fl. 1 Bedroom Bungalow

My place is across the street from the beautiful Pithlaschascotte River, close to parks, restaurants, kayak rentals, boat rentals, and dining. The Bungalow is nestled among 150 year old oak trees not far from downtown New Port Richey. The Bungalow is in the rear of a law office building. Nice porch with seating to enjoy your glass of wine at the end of the day.. You’ll love my place in a 1920 building with an old Florida feel. My place is good for couples and solo adventurers.

Oct. 15 – 22

$130 CAD per night

Superhost

Guesthouse in Tarpon Springs

4.84 out of 5 average rating, 286 reviews

Papa Bear's Cottage Two Bedroom Vacation Rental

A simple, yet magical second-story guesthouse, nestled into a yard of Spanish Moss and Magnolia trees, above a garage (no one will be in the guest house but you!). Minutes from downtown Tarpon Springs and the famous Sponge Docks, and 15 minutes from beautiful Gulf beaches, 30 minutes from Clearwater Beach. Hunkered in at the end of a private drive, on over two acres of quiet, enchanting land. You and your crew will enjoy the respite, nature, and coziness of Papa Bear's Cottage!

May 27 – Jun. 1

$186 CAD per night

Guest favourite

Tiny homes in Tarpon Springs

4.88 out of 5 average rating, 128 reviews

Driftwood Surf Shack

This unique Surf Shack is a guest home that sleeps up 4 & still plenty of room to relax inside or outside on the large wood deck situated under a beautiful oak tree. Located in the historic district Tarpon, just blocks from Downtown, the famous Sponge Docks & Craig Park where you can watch dolphins feed at sunset in the many Bayous. Close to beaches, shopping, restaurants, breweries, boat excursions, water sports & the Pinellas Trails you will never get bored in this town!

Jul. 13 – 20

$165 CAD per night

Guest favourite

Guesthouse in New Port Richey

5.0 out of 5 average rating, 103 reviews

Palm Hideaway on the Cotee River

Relax on the river at Palm Hideaway-a luxury escape to the Gateway of Tropical Florida. Our cozy guest cottage was completely renovated in 2022 & is nestled amid lush greenery on the Pithlachascotee "Cotee" River in New Port Richey. Sleep in the king size bed & have coffee or tea on your Tiki patio rain or shine. Guests have shared access to the river from the park-like backyard & can enjoy a fire in the fire pit or paddle the kayaks.

Jan. 2 – 9

$154 CAD per night

Guest favourite

Home in Tarpon Springs

4.95 out of 5 average rating, 176 reviews

Tree House Treasure

We're a quiet, small, serene old neighborhood on the end of a cul-de-sac and nearly floating on a lagoon! Florida nature at it's finest. The home is just 4 feet off the sea wall so the home is best suited for adults that are looking for that quiet get-a-way. Upper has 2 beds & a tri-fold mattress. The lower is an office for the maintenance team. No smoking, vaping, or illegal drugs permitted.

Aug. 10 – 17

$195 CAD per night