Waterfront vacation rentals in Holiday

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Holiday

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Palm Harbor

4.94 out of 5 average rating, 184 reviews

Private Entrance/Well Appointed Suite/ Lake View

Private entrance/ Private suite/bath w/ walk in closet. Microwave/fridge. Convenient parking. Beautiful view of the lake and all its wildlife. Everything you need to go to the beach is in the room, beach towels, umbrellas, beach mat. Due to host allergies, NO pets/animals/service animals. No smoking/vaping/drinking/drunkenness. Sensitivities? I do not use plug-ins, scented sprays, scented detergents/dryer sheets. If traveling w/ a service animal, kindly, please choose another Airbnb property.

Sep 17 – 24

G$16,986 GYD per night

Superhost

Apartment in Tarpon Springs

4.9 out of 5 average rating, 10 reviews

Waterfront seasonal studio

Attached 1-bath studio seasonal rental in Tarpon Springs on the bayou, comes w/ everything you need and is surrounded by everything you'll want to do. Includes in-unit washer/dryer. Also has private patio and fenced courtyard with water view. Walking distance to Whitcomb Bayou, the historic Sponge Docks with boat rides, dolphin tours, shopping, authentic Greek food, & fabulous seafood. Minutes to pretty beaches and parks, this attached unit lets you embrace nature on the nearby Pinellas Trail.

Jan 11 – 18

G$15,260 GYD per night

Superhost

Apartment in Hudson

4.81 out of 5 average rating, 108 reviews

Gulf Access Waterfront Fully Furnished Home W Dock

Walking distance to the Hudson beach and restaurants . Grocery stores and shopping plazas nearby. Short drive to the Sun West Beach park. 45 minutes drive to the Clearwater Beach. 50 minuted to Tampa airport. Backyard canal directly lead to the Gulf. Take your boat or canoe and go fishing, looking for dolphins, watching the sunset ... This home features large living room with hardwood floor, granite counter tops, fully equipped kitchen, front load washer and dryer, nice leather sofa, ...

Sep 20 – 27

G$23,428 GYD per night

Superhost

Home in Holiday

4.91 out of 5 average rating, 106 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 20 – 27

G$54,482 GYD per night

Superhost

Cottage in Hudson

4.84 out of 5 average rating, 125 reviews

My Happy Place!

Comfortable, homey, relaxing, Florida vacation home. It's on a canal where you can bring your boat. We have a 20 foot floating dock. Fishing and swimming off the dock are a great pass time. A five minute ride by boat, to the beautiful Gulf of Mexico. We have two old canoes for you to check out the canals, the island and sand bar just past the main canal. Close to all stores, places to eat, and many county and state parks. At night relax on the porch and watch the fish swim.

Aug 10 – 17

G$18,132 GYD per night

Guest favorite

Farm stay in Odessa

4.92 out of 5 average rating, 59 reviews

The Cabins At Cahaba - Cabin 1

Enjoy the tranquil surroundings of a working farm where we produce the freshest micro-greens and other delicious edibles for distribution all over the world. Located north of Tampa, our farm is centrally located and just a short drive from Tampa International Airport and downtown Tampa, award winning beaches, major sports venues, equestrian centers, hiking trails, birdwatching, and shopping. Don't want to venture out? Sit back, relax and enjoy the peace and quiet of this natural setting.

Feb 27 – Mar 6

G$19,070 GYD per night

Guest favorite

Guesthouse in Port Richey

4.9 out of 5 average rating, 51 reviews

Waterfront Oasis- Pool/Hot Tub

Cozy Coastal Oasis in Port Richey Welcoming cozy retreat is a peaceful location for you to relax and enjoy a beautiful sunset. This beachy oasis is situated at the end of a cul-de-sac and located on a saltwater lagoon that leads out to the Gulf of Mexico, so bring your paddle boards and kayaks to enjoy your favorite outdoor water activity. Your family will be close to everything when you stay at this centrally-located place. Restaurants and Grocery stores 5-10 minutes away!

Jan 10 – 17

G$30,221 GYD per night

Superhost

Home in Holiday

4.88 out of 5 average rating, 110 reviews

Waterfront, Sunsets & Heated Pool & pet Stay Free!

Close to the beach, family activities, public transport, and the Tampa Airport. You’ll love my place because of the ambiance, the outdoors space, the water view, & the sunsets, PRIVATE Heated pool and VERY comfy beds! I provide fishing poles, tackle box My place is great for everyone and furry friends (pets) too!. Third bedroom is Florida room with sliding glass door. Two twin beds and desk. dinning table. Let me know about your pets. Your pets stay free. Totally fenced yard.

Jul 24 – 31

G$42,773 GYD per night

Superhost

Guest suite in New Port Richey

4.91 out of 5 average rating, 110 reviews

Tropical Suite on Treasure Island’s Bayou NPR

Located in a quiet neighborhood on Treasure Island in NPR. This is a beautiful waterfront vacation rental for two... Enjoy a romantic evening on your private, covered balcony after a day of lounging poolside or fishing and kayaking from the backyard. Being west of 19 and close to Main St, we are in walking distance of all of the fun events in New Port Richey. We hope that you have some time to enjoy the local restaurants, pubs, and events in Downtown New Port Richey!

Sep 10 – 17

G$24,307 GYD per night

Superhost

Home in New Port Richey

4.91 out of 5 average rating, 82 reviews

Steps to dwnt/7min to beach/queen bed/Free parking

Welcome to this brand new remodeled Airbnb home in New Port Richey, FL that is only one block from a historical downtown area that has shops and restaurants. The closest beach Green Key Beach is 5 min away by car. The home has a beachy vibe and features all brand-new furniture, appliances, and a modern kitchen. The home is clean and inspiring for your vacation or remote work needs. It is located in a lovely neighborhood with great proximity to everything you might need.

Jun 14 – 21

G$18,753 GYD per night

Guest favorite

Home in Holiday

5.0 out of 5 average rating, 13 reviews

*NEW* Riverside Retreat w/Pool

Take it easy at this unique and tranquil getaway. Welcome to our Riverside Retreat where you will enjoy incredibly relaxing peaceful days, and sunset views. Recently renovated 2 Bedroom, 2 Full Bathroom, pool home with dock and privacy fenced backyard on the Anclote River. This home is fully equipped and is ready for you to enjoy. Conveniently located and only a 9-minute drive to the World-famous Sponge Docks and minutes from our award winning beaches…

Oct 4 – 11

G$38,822 GYD per night

Guest favorite

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.

Sep 30 – Oct 7

G$19,348 GYD per night