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Vacation rentals with a pool in Holiday

Find and book unique homes with a pool on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Holiday rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Top guest favorite
A private pool area features a spacious swimming pool with a gentle fountain. Two red lounge chairs are positioned on the patio, alongside a light blue inflatable ball and a colorful floating mattress. Lush greenery surrounds the enclosure, enhancing the tranquil atmosphere.
Home in New Port Richey
5 out of 5 average rating, 62 reviews

Luxurious Pool Private Oasis, Nearby Beaches

Top guest favorite
The exterior of the home features a welcoming entrance and landscaped yard, showcasing vibrant tropical plants and a decorative pathway. An inviting pool area includes seating along the deck, with loungers arranged for comfort. Scenic water views are visible from a nearby deck, with kayaks ready for use.
Home in Holiday
5 out of 5 average rating, 30 reviews

Waterfront, Beach, Pool,Kayaks near Islands, Parks

Top guest favorite
A spacious screened-in pool area features a heated swimming pool, surrounded by a white deck. Sun loungers are positioned beside the water, with a shaded seating area nearby. The fenced backyard is visible in the background, offering privacy and open space.
Home in New Port Richey
5 out of 5 average rating, 80 reviews

Relaxing Beach-Theme Pool Home!

Guest favorite
An inviting outdoor space is showcased, featuring a private saltwater pool under a screened enclosure. Sun loungers are positioned beside the pool, with a view of the Anclote River visible through the screening. A 50” TV is mounted nearby for entertainment.
Home in Forest Hills
4.9 out of 5 average rating, 20 reviews

Waterfront Oasis-Tarpon Sunsets-Pool-Kayak-Fishing

Guest favorite
The outdoor area features a fully enclosed heated pool with a spacious deck. Lounge chairs and tables surround the pool, while string lights add a subtle ambiance. Large sliding glass doors offer a view of the indoor spaces, enhancing the connection between indoor and outdoor living.
Home in Port Richey
4.95 out of 5 average rating, 73 reviews

Heated pool, golf, grill! Fun-Packed Family Oasis

Top guest favorite
An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.
Home in Palm Harbor
4.95 out of 5 average rating, 78 reviews

Private pool, Golf Cart, Completely Renovated!

Top guest favorite
A private heated pool is surrounded by a spacious patio area, featuring two lounge chairs. The pool offers a clear view of the canal, while palm trees line the shoreline, contributing to the serene outdoor ambiance.
Home in Palm Harbor
4.98 out of 5 average rating, 60 reviews

Luxury Waterfront w/ Private Heated Pool

Guest favorite
A spacious living area features high ceilings and natural light, with a comfortable seating arrangement that includes a gray sectional and armchairs. A modern coffee table sits at the center, complemented by a decorative lamp and plants. The area seamlessly connects to a dining space with a large table.
Home in Wesley Chapel
4.98 out of 5 average rating, 47 reviews

Designers Villa @ Saddlebrook

Condo rentals with a pool

Top guest favorite
A comfortable living area features a neutral-colored sofa, a round dining table, and a ceiling fan. Large sliding glass doors provide access to a balcony, allowing natural light to fill the space and offering views of palm trees outside.
Condo in Tampa
4.92 out of 5 average rating, 199 reviews

Waterfront Condo - Sunset View of Tampa Bay

Guest favorite
A large swimming pool is surrounded by lush palm trees and lounge chairs. The pool features a winding shape with a hot tub adjacent to it. Resort-style amenities are visible in the background, with a two-story building lined with windows overlooking the pool area.
Condo in Clearwater
4.97 out of 5 average rating, 130 reviews

Immaculate 2 BR/2 BA Retreat, A+ Pool, 3m to Beach

Guest favorite
A private balcony offers a cozy seating area with blue cushions and a small table. Palm trees and beach views are visible beyond the railing, where the sand meets the water, enhancing the relaxing beach atmosphere.
Condo in Independence Square
4.9 out of 5 average rating, 109 reviews

Oceanfront View, Spacious Townhouse, Heated Pool

Top guest favorite
A spacious heated pool is surrounded by lush palm trees and well-maintained landscaping. Comfortable lounge chairs are positioned along the poolside, providing ample relaxation spots. The pool area is framed by the community buildings, creating a welcoming atmosphere for guests.
Condo in Clearwater
4.99 out of 5 average rating, 119 reviews

Seasalt Breeze private unit No hidden fees

Superhost
The image captures a view from the condo balcony, showing a clear blue sky and the tranquil Gulf of Mexico. The pool area is visible, featuring a large swimming pool surrounded by lounge chairs. Beach umbrellas dot the sandy shore, providing a vibrant contrast.
Condo in Indian Shores
4.95 out of 5 average rating, 121 reviews

Tropical Beachfront Penthouse-Beach Cottages

Guest favorite
A clear view of the pool area features a well-maintained heated pool surrounded by paved walkways. Lounge chairs are positioned nearby, with lush greenery and well-kept bushes framing the scene, enhancing the tranquil outdoor environment.
Condo in Clearwater Beach
4.93 out of 5 average rating, 149 reviews

Beachfront Condo with Centerline Sunsets

Top guest favorite
Condo in Treasure Island
4.98 out of 5 average rating, 197 reviews

Spectacular beach to bay views from this resort.

Top guest favorite
A beachfront balcony features a round table with four striped chairs, inviting outdoor relaxation. The expansive view showcases sandy shores meeting the calm turquoise waters under a clear blue sky. Sliding glass doors provide easy access to the living space.
Condo in Indian Shores
4.99 out of 5 average rating, 111 reviews

Five Star Beachfront Condo Newly Renovated

Other vacation rentals with a pool

Top guest favorite
A spacious heated pool area is surrounded by a screened enclosure, featuring clear blue water under bright sunlight. A view of the waterfront is visible beyond the pool, with palm trees and homes reflected in the water. Potted plants add a touch of greenery.
Home in Hudson
5 out of 5 average rating, 38 reviews

Beautiful sunsets, waterfront 2/2 pool home

Superhost
A serene backyard showcases a heated in-ground pool with clear blue water. A dock is visible in the distance along the canal, framed by palm trees and a decorative dolphin sculpture. The brick patio features seashells and offers a peaceful view of the waterfront.
Home in New Port Richey
4.68 out of 5 average rating, 145 reviews

Gulf Harbors Getaway Home with Pool

Superhost
A bright and inviting bedroom features a spacious bed adorned with a colorful quilt and decorative pillows. Natural light fills the room through a window, complemented by vibrant orange curtains. A bedside lamp and wall art add character to the cozy space.
Guest suite in Holiday
4.86 out of 5 average rating, 7 reviews

Cheery Private Room Efficiency-Kitchenette

Top guest favorite
A collage showcases various aspects of the home, including a spacious living area with a dining space, a modern kitchen with bar seating, and a serene outdoor pool area surrounded by lounge chairs. The front view highlights the two-car garage and well-maintained landscaping.
Home in Port Richey
4.96 out of 5 average rating, 26 reviews

Heated Pool, Fire Pit & Fishing Dock – Book Now!

Top guest favorite
A quaint cottage exterior is seen with a light blue facade and a welcoming porch. Two turquoise chairs are positioned beside a small table, under strings of decorative lights. A net with shells adds a coastal touch, and a stone feature stands nearby.
Guesthouse in New Port Richey
4.99 out of 5 average rating, 72 reviews

Cottage on the Cotee River

Top guest favorite
A serene outdoor space is illuminated by string lights hanging from trees. A winding stone path leads to wooden steps ascending to a deck. Lush green grass surrounds a picnic table positioned on one side, enhancing the tranquil atmosphere of the lakefront setting.
Home in Palm Harbor
5 out of 5 average rating, 7 reviews

Lakefront Gem Near Clearwater

Top guest favorite
A lushly landscaped golf course area is surrounded by palm trees, offering a serene view of the lake. A vibrant green putting surface is visible, while comfortable seating options in orange are placed nearby. A luxurious heated jacuzzi sits on a wooden deck, ready for relaxation.
Home in Palm Harbor
4.97 out of 5 average rating, 39 reviews

Preservation-Jacuzzi-Golf- Kayaks-Fishing-Pool !

Top guest favorite
A private pool area is showcased with a clear blue pool surrounded by a deck. Lounge chairs are positioned nearby under a shaded canopy, while a seating area with a canopy is visible in the background. Lush greenery frames the scene, enhancing the space.
Guest suite in Holiday
4.92 out of 5 average rating, 53 reviews

Peaceful Meadows

Quick stats about vacation rentals with a pool in Holiday

  • Total rentals

    30 properties

  • Nightly prices starting at

    R704 ZAR before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Pasco County
  5. Holiday
  6. Rentals with pools