Holiday rentals with outdoor seating in Holiday

4.95 out of 5 average rating, 193 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

5 out of 5 average rating, 104 reviews

An aerial view showcases a modern two-story house surrounded by water and greenery. A private boat dock is positioned in the foreground, along with a manicured lawn featuring a putting green and colorful kayaks. Solar panels are visible on the rooftop.

Flat in Tarpon Springs

Waterfront studio great for Pasco scallop season!

Studio Apartment on ground level. Direct access to Gulf of Mexico w/short boat/kayak ride. Queen-size bed and pullout sofa. Microwave, coffee maker, stove top, refrigerator/freezer, 62" Smart TV, gas BBQ. Hot tub (only available from Oct 1st-May 31st) Enjoy the sun, beautiful nature of Anclote River with 3 kayaks and 3 paddle boards. Daily sightings of dolphins, manatees and many species of birds passing by. Fish right off the sea wall. Beach is a short 2-miles away. Overnight boat docking.

A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.

4.96 out of 5 average rating, 104 reviews

Paradise!Renovated waterfront pool home.Sunsets!

No hurricane damage!Sunsets to die for! Completely remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard &sometimes you can spot dolphins!Watch birds, ducks, manatees. All new appliances and granite countertops.New quartz bathroom cabinets!New tiles throughout the house including Florida room. Cooler,chairs&umbrella, kids beach toys that you can take to the beach.Bonfire pit.Grill.Heated pool for a fee. Come,relax&enjoy

4.99 out of 5 average rating, 286 reviews

A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.

Home in Port Richey

Heated & Screened in Pool/Coffee Bar/Fully Stocked

🏡 Private Pool House with Large Covered & Screened-In Porch Relax and unwind in this inviting private pool home, featuring a large covered and screened-in porch—perfect for enjoying the outdoors without the bugs. 🌊 Heated Pool Take a dip in the private pool, heated year-round with an electric heat pump (weather permitting), offering comfort no matter the season. Whether you're sipping coffee on the porch or enjoying a swim, this cozy retreat is ideal for a peaceful and private getaway.

Cottage in Tarpon Springs

The exterior of a charming blue bungalow features a pink front door. A pink chair is positioned next to the door, adorned with greenery and colorful florals. The landscaped yard showcases a stone pathway, bordered by plants and palm trees, creating an inviting entrance.

4.95 out of 5 average rating, 100 reviews

Charming Blue Bungalow With Amazing Yard

Don't miss a stay at the Blue Bungalow while enjoying the historic and beachy town of Tarpon Springs. This spacious 2-bedroom 1 bathroom home built in 1936 has been tastefully updated but still has much of it's original charm. Then there's the best backyard with a grill, dining area, a fire pit, cornhole court, and a spacious deck. The home is located minutes from several beaches, a dog park, the Pinellas Trail and Greek town. Restaurants, breweries and fun community events are abundant.

Home in Downtown New Port Richey

The modern kitchen features sleek white cabinetry and stainless steel appliances. A spacious island is centered, offering additional countertop space. Natural light is provided by a window above the sink, enhancing the airy feel of the room. Decorative elements include a plant and minimalistic kitchenware.

4.94 out of 5 average rating, 107 reviews

Downtown Darling

Bring the whole family to this great property with lots of room for fun. 3 king bedrooms with pillow top mattresses, one bunk bed room that sleeps 3 kids. Large kitchen, large laundry room. Home has been completely renovated. Less than a 10 minute walk to all the activities on Main Street, Restaurants, breweries, roof top restaurant, axle throwing bar, sims park with weekly activities and a brand new playground and splash pad for the kids. Walk in the evening down the river boardwalk.

Guest suite in Port Richey

A well-designed studio layout is shown, featuring a spacious sleeping area with a textured blanket draped over the bed. The kitchen area includes sleek white cabinetry, modern appliances, and a dining setup with two stools at a counter, inviting guests to relax and dine comfortably.

4.99 out of 5 average rating, 108 reviews

Cozy Studio Getaway w/ Beach Essentials

Enjoy an unforgettable stay in our warm and inviting studio, thoughtfully designed to provide the perfect blend of comfort and style. Whether you're here for a relaxing getaway or a work-related visit, this space offers the ideal atmosphere to unwind and feel at ease. Set in a safe and strategically located area, you'll have quick and easy access to a variety of restaurants, shops, highways, hospitals, and more. You’ll find yourself surrounded by peace, privacy, and a sense of home.

A view of Lake Conley is depicted, showcasing calm waters under a clear blue sky. Lush trees line the shore, with a walkway and dock visible on the left, offering access to the water. The scene reflects a tranquil outdoor environment.

4.87 out of 5 average rating, 135 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.

4.98 out of 5 average rating, 111 reviews

Flat in Holiday

Lake access studio near Tarpon Springs.

🌿 Enjoy a quiet private studio for 2 near Tarpon Springs beaches, perfect for a relaxing getaway, work trip, or calm stay close to nature. 🌅 Step through a short hallway to reach the peaceful outdoor lake area, then return to a queen bed, fast WiFi, workspace, fully equipped kitchen, private parking, and 24/7 self check-in. 📍 Close to Fred Howard Park, Sunset Beach, Dunedin, Clearwater, New Port Richey, restaurants, shops, and Tampa. Clean, easy, 5-star stay. ⭐

4.95 out of 5 average rating, 110 reviews

Guest suite in Holiday

HolidaySpring|CozyPrivate Apt near beach|2 parking

Private & cozy apartment with independent entrance and free parking for two vehicles. Located in a quiet and safe area just minutes from the beach and Tarpon Springs (“Little Greece”) and just minutes from Fred Howard Park Beach.Enjoy a fully equipped kitchen, comfortable bedroom with work desk, Smart TV, fast WiFi, spacious bathroom, and outdoor terrace. Perfect for couples, small families, or remote workers Scan the QR in the last photo for a full video tour

A sparkling saltwater pool is featured in the backyard, with a gently curving shape and a clear blue surface. The area is fenced for privacy, with a well-maintained lawn and a sunny sky visible above.

4.97 out of 5 average rating, 117 reviews

Private 3 Bedroom House w/ Heated SaltWater Pool

Spend your holidays in HOLIDAY, FL! We welcome you to our cozy, fully renovated house with a large, heated private in-ground, SALTWATER pool. The house has three bedrooms and enough room for 7 guests, along with two full bathrooms. The kitchen is stocked with all cookware essentials needed. The house has everything you need for vacations, so you may kick back and relax. It is centrally located to many attractions if you're up for a drive.

An aerial view captures a cozy lakeside home surrounded by lush greenery and palm trees. The screened-in private pool is visible, along with a nearby dock extending into the water. A fire pit area is seen, providing a space for gatherings. Scenic views enhance the outdoor experience.