Vacation rentals with outdoor seating in Holiday

The exterior of the retro home features a gravel driveway bordered by illuminated garden lights, creating a welcoming ambiance. Two front doors are framed by windows, and potted plants add a touch of greenery. A white fence encompasses the property, enhancing its charm against a twilight sky.

4.95 out of 5 average rating, 192 reviews

King Bed Luxury & Queen 2/1/1—Patio+Laundry+3TVs

Transport back to the 50’s when staying at this coastal retro 2 BD/1BA home. The charming mid-century design throughout boasts top-of-the-line amenities including 3 Roku Smart TV’s, a fully equipped kitchen, a delightful King & Queen mattress, a dedicated workspace, an enclosed garage, outdoor patio, beach towels, a washer & dryer. Indulge in all the luxuries while being near Tarpon Springs/Sponge Docks(4.9mi) Anclote Beach(4.8mi), Honeymoon Island State Park(16.2mi), several restaurants & more!

A comfortable living area features a beige sofa adorned with orange accent pillows, flanked by two stylish lamps. A round wooden coffee table is positioned on a decorative rug, with modern wall art enhancing the space. A red armchair adds a pop of color to the setting.

4.94 out of 5 average rating, 108 reviews

Cozy 3-bed home close to beautiful beaches.

Newly updated 3-bedroom, 2-bath home close to everything. Centrally located, within 20-30 mins to the famous Tarpon Springs Sponge Docks, Sunset, Howard Park, Honeymoon Island, Anclote River Park & Clearwater Beaches, Busch Gardens Theme Park and Weeki Wachee. Close toTampa International Airport. Numerous country club golf courses, waterfront restaurants/bars within a short drive. Enjoy your home away from home with everything you need and more with a BBQ Grill/ Fire pit and other amenities.

Vacation home in Tarpon Springs

A cozy living room is displayed with a green sofa positioned beside a plant. A coffee table sits at the center, accompanied by a light fixture and a wall art piece. Natural light filters through the window, illuminating the warm wood flooring.

4.97 out of 5 average rating, 143 reviews

Modern Home Great Location

Welcome to your home away from home. Our guests’ comfort is our priority. Equipped with all your creature comforts and surrounded by modern fixtures and decor to ensure a wonderful vacation. Open Floor plan, huge kitchen, and two cozy bedrooms. Walking distance to all the local restaurants and attractions, without the noise to keep you up at night; you couldn't choose a better location Please note: this is a duplex property, so you'll be sharing the building but enjoying your own private space.

4.97 out of 5 average rating, 175 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

Cottage in Tarpon Springs

The front exterior of Cooper Cottage features a welcoming porch with two black rocking chairs and potted plants. A pathway leads to the entrance, while large windows allow natural light to illuminate the space. Lush trees provide shade and a tranquil atmosphere.

4.99 out of 5 average rating, 179 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.

Apartment in Tarpon Springs

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.

5 out of 5 average rating, 100 reviews

Waterfront studio w/Hot Tub and Putting Green

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.

5 out of 5 average rating, 203 reviews

Apartment in Timber Oaks

Jungle Studio 1BR/1BA, Fenced Patio, Full Kitchen

🌿 MAY SPECIAL‼️Escape the stress & enjoy a relaxing, private & affordable Florida Staycation or Workation! This quiet countryside studio located near everything in town features: A separate entry, a spacious bathroom, 2 full closets for long stays, 1 BE w/a queen bed, a full kitchen, high-speed WiFi , a fenced patio & 2 FREE parking spots ⭐️Prime Location ⭐️ 10 min to hospitals (ideal for nurses!), shops, beaches, Tarpon Springs 30 min to Tampa Perfect x couples, golfers & family visitors

4.93 out of 5 average rating, 150 reviews

Luxury Private Pool House ! Mackarosa ! Tampa Bay

Experience comfort and style in this beautifully renovated home with high ceilings and elegant design. Bright, airy spaces create a relaxing atmosphere, and the king bed offers restful sleep after a day of travel or exploring. Fully equipped kitchen. Private pool with solar heating — perfect year-round. Airport – 35 min • Beaches – 19 min No smoking. No pets. Professionally cleaned and disinfected after each stay. Located in a quiet, safe neighborhood — ideal for families and peaceful stays.

4.96 out of 5 average rating, 110 reviews

A well-equipped kitchenette features a granite countertop with three bar stools. Natural light enters through a window, illuminating the space, which is complemented by a small dining area and a comfortable seating arrangement. A wall-mounted TV and a lamp add to the cozy ambiance.

Farm stay in Odessa

Cabin 3 - Nasturtium Nest

Discover the peaceful retreat at Cahaba Cabins, a hidden gem nestled on a working microgreen farm in Odessa. The property offers a unique blend of charm and agricultural expertise. We offer three cozy cabins where you can unwind and reconnect with nature while still being close to everything the Tampa Bay area has to offer. Each cabin offers two queen beds, a private bathroom, and a kitchenette—providing all the essentials for a relaxing stay. We look forward to seeing you on the Farm!

4.91 out of 5 average rating, 134 reviews

A private swimming pool is surrounded by a screened patio, with colorful floatation devices resting on the clear water. Lounge chairs are positioned nearby against a bright yellow wall. Natural light floods the area through glass doors, creating a refreshing atmosphere.

Home in Forest Hills

Sunny Pool Home • Near Tarpon & Beaches 5 mi

🌴 Heated private pool oasis (Nov–Mar) 5 mi to Tarpon Springs—ideal to recharge. 🏡 Private patio for BBQ and outdoor time in a quiet area for great sleep. Perfect for families & friends: fast Wi-Fi + workspace, fully equipped kitchen, 🔑 24/7 self check-in, and 🚗 on-site parking. Easy access to Dunedin, Clearwater, Tampa, and beaches (times vary with traffic). ✨ Note: pool heat available Nov–Mar (weather permitting). ⏳ Last-minute promos active—book and lock in your dates!

4.96 out of 5 average rating, 120 reviews

A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.

Home in Odessa

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

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.

4.96 out of 5 average rating, 105 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.

Popular amenities for Holiday outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.94 out of 5 average rating, 64 reviews

Adirondack chairs are arranged on a pebbled area facing a tranquil canal, with a sunset casting a warm glow over the scene. The serene water reflects the colorful sky, surrounded by lush greenery and residential homes lining the opposite bank.

Home in Forest Hills

Holiday fun canal home

5 out of 5 average rating, 24 reviews

Relaxing Getaway in New Port Richey

Superhost

4.88 out of 5 average rating, 8 reviews

Sunny family Oasis by Tarpon *Hot Tub & Playground

5 out of 5 average rating, 6 reviews

Endless Summer

4.96 out of 5 average rating, 74 reviews

A light-filled living area features a spacious sectional sofa and a wooden table with a decorative chair. Natural light streams in through large windows with shades, illuminating the neutral color palette and coastal-inspired decor, creating a relaxed environment.

Home in Forest Hills

*NEW* Riverside Retreat w/Pool

4.89 out of 5 average rating, 9 reviews

Home with access to the Gulf.

A private pool area features sparkling blue water, surrounded by a well-maintained deck. A wooden pergola offers shaded seating nearby, while tropical plants provide a natural backdrop. The sky is mostly clear, creating a bright and inviting atmosphere.

5 out of 5 average rating, 54 reviews

Florida style home !

The exterior of the home is showcased with a well-maintained lawn, bordered by a circular driveway. The facade features neutral stone and brick materials, with a welcoming entrance illuminated by soft outdoor lighting. A flagpole stands proudly at the front, adding a classic touch.

5 out of 5 average rating, 28 reviews

Deluxe 3bd/2ba w/Heated Pool

Apartment rentals with outdoor seating

4.98 out of 5 average rating, 380 reviews

A well-appointed bedroom features a spacious bed with crisp white sheets and a contemporary headboard. Nightstands with lamps are positioned on either side, while a large artwork piece hangs above the bed. The room's floor is adorned with elegant marble tiles, enhancing the overall aesthetic.

Apartment in Tampa

Northdale Apartment

4.97 out of 5 average rating, 424 reviews

A modern bathroom featuring a round mirror above an elegant wooden sink with a metallic bowl. Exposed brick walls and dark accents create an industrial feel. A sleek, black toilet complements the stylish glass shower, which is designed with contemporary tile.

Apartment in Tampa

Hyde Park "Industrial-chic" with Private Backyard

4.91 out of 5 average rating, 139 reviews

A compact bedroom features a neatly made bed adorned with decorative pillows. A small nightstand with a lamp is positioned beside the bed. Wall art depicting floral designs enhances the room's decor. A fan hangs from the ceiling, providing airflow.

Apartment in Port Richey

La Palma

4.97 out of 5 average rating, 145 reviews

A cozy living area features a blue sofa adorned with light-colored pillows, positioned beside a round wooden coffee table. A stylish light fixture hangs from the ceiling, illuminating the space. A framed artwork of a cow is displayed on the wall, adding a charming touch.

Apartment in Dunedin

Overlooking Downtown Dunedin Two Bedroom apartment

4.9 out of 5 average rating, 125 reviews

A spacious living area features large windows offering views of lush greenery. A wooden coffee table is centered between two leather sofas and a light-colored couch. A ceiling fan overhead enhances air circulation, while the adjoining kitchen is highlighted by wood accents and modern appliances.

Apartment in Ozona

Bright and Airy Ozona on the Gulf

4.85 out of 5 average rating, 145 reviews

Apartment in Clearwater

Lovely 1 bedroom rental & patio, close to beach

Apartment in Historic Hyde Park

A cozy living area features a brown sofa paired with two woven stools. A fireplace is elegantly styled with stacked logs, while soft lighting illuminates the space. A small dining table with wooden chairs is positioned near a window, enhancing the inviting atmosphere.

4.98 out of 5 average rating, 174 reviews

Casita Palma ~ Old Hyde Park (Casita Palma)

4.96 out of 5 average rating, 109 reviews

Two turquoise Adirondack chairs are positioned on a stone patio, shaded by a large umbrella. Beyond, a serene waterway reflects the sky, with boats visible along the banks. Nearby, kayaks are arranged for guest use, enhancing the outdoor recreational setting.

Apartment in Sea Pines

Southwind Sunsets

Condo rentals with outdoor seating

4.97 out of 5 average rating, 143 reviews

Condo in Clearwater

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

Condo in Indian Rocks Beach

The inviting living space is furnished with a blue sofa, two armchairs, and a white coffee table. A starfish-patterned rug adds a nautical touch. Natural light filters through window blinds, illuminating the area. The open layout connects to the kitchen, visible in the background.

4.97 out of 5 average rating, 132 reviews

Beach Across the St | No Stairs |Parking in Front!

4.97 out of 5 average rating, 213 reviews

A vibrant, themed living area features colorful hanging lamps and intricate wall decorations. Lush greenery is present, alongside a mixture of patterned seating arrangements. Large glass doors open to a balcony, allowing natural light to fill the space and offering a view of the outdoors.

Condo in Tampa

Tiki Themed Waterfront Condo on Tampa Bay

Condo in Independence Square

Beach chairs are arranged under a blue umbrella on the sandy shore, inviting relaxation. Each chair is brightly colored, accompanied by cushions and beach towels. In the background, a two-story condo building is visible, framed by a clear blue sky.

4.96 out of 5 average rating, 165 reviews

Luxury-Direct Beach Access-Updated

Condo in Clearwater Beach

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

4.9 out of 5 average rating, 445 reviews

Amazing views on beachfront

Condo in Indian Rocks Beach

4.85 out of 5 average rating, 102 reviews

Walk to Beach, Bars, and Restaurants Nearby

Condo in Gulf Island Beach and Tennis Club

A spacious living area features a dark sectional sofa and a large flat-screen television. Brightly colored artwork adorns the walls, and a glass coffee table adds a modern touch. Natural light enters through a sliding glass door, with views of the outdoor patio.

4.91 out of 5 average rating, 105 reviews

Florida Breeze