Holiday rentals with a pool in Holiday

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Holiday

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Home in Tarpon Springs

4.98 out of 5 average rating, 125 reviews

Heated Pool, Close to Beaches!

Welcome to Tarpon House Florida, located in the exclusive and historic Tarpon Springs. Our home is a tropical oasis. Perfect for families, couples, and anyone who needs the space to spend time together or enjoy some privacy for enjoyment and relaxation. 10% discount for Military, First Responders, Teachers, friends and family - book & message me, I'll apply the discount, that's it! Completely renovated with all new furniture. Link to 3D Tour of the house is in my guidebook (under my profile)

Guest favourite

Condo in Palm Harbor

4.82 out of 5 average rating, 178 reviews

Lakeside 2- Bed Apartment Near Clearwater Beaches

Ideally located on Florida's Gulf Coast minutes from many of America’s best beaches. The apartment is situated on the shores of beautiful Lake Tarpon, just north of Clearwater. The big exciting city of Tampa is just 30 mins away with the big theme parks in Orlando only 90 mins away. The pool & jacuzzi are also by the water & decking. Come stay, relax & recharge your batteries in a comfortable peaceful setting yet close by you have all the activities & amenities that you could ever wish for!

Guest favourite

Guesthouse in Palm Harbor

4.96 out of 5 average rating, 258 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower, Double sink Vanity. Access to shared pool and patio, backyard and Sundeck. Room includes small refrigerator/freezer, Microwave, Coffee maker, Espresso, Iron and much more. Bistro set in room. Private entrances to room and patio/backyard. Cable TV, Netflix and Wi-Fi included. Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Guest favourite

Guest suite in Tarpon Springs

4.96 out of 5 average rating, 119 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

Superhost

Condo in Paradise Lakes

4.8 out of 5 average rating, 113 reviews

Be One with Nature Clothing Optional Premium Condo

Relax in your birthday suit in a fun clothing-optional Paradise lakes Resort. Modern furniture sleeps up to 4 People with a King Size Bed and a leather sleeper sofa in living room with Memory Foam mattress. Full kitchen with refrigerator, oven range and microwave for cooking, coffee maker, washer and dryer for laundry, 2 TVs, and a bath tub for relaxing. The clubhouse 2 Swimming Pools, Hot Tub, events like Karaoke, Live Bands and more (fees vary by days of week). Thank you and enjoy!

Superhost

Home in Holiday

4.89 out of 5 average rating, 121 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.

Guest favourite

Home in Hudson

4.93 out of 5 average rating, 108 reviews

Oasis Getaway

Relax with the whole family at this peaceful place to stay. Perfect Getaway with amazing sunset views from the upstairs balcony and a floating dock on a canal perfect for kayaking and manatee sight seeing. This canal will also take you straight to the ocean. Very spacious home with a tennis table located on the first floor and a beautiful pool to enjoy! Close to many attractions like Weeki Wachee Springs, Outdoor trails, a Marina, Water Park, Hudson Beach and great seafood restaurants.

Guest favourite

Guesthouse in Spring Hill

5 out of 5 average rating, 133 reviews

J&M Homestead

Relax with the whole family at this peaceful place to stay. Close to I-75 and Suncoast Parkway in Pasco County. Located north of Land O Lakes, Florida, in Pasco Trails, a gated community of acreage and horses. Outlet mall, many eating establishments and sports complexes within half-hour drive. We have had to institute a policy of "no smoking. To be clear, we are retired couple who live in the main house. The apartment is attached but has its own entrance and is self contained.

Guest favourite

Home in Tarpon Springs

4.96 out of 5 average rating, 339 reviews

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

This home is ideally located near Florida's beautiful Sunset Beach and Howard Park Beach - only 17 miles from Clearwater Beach. Take a short ride to world famous attractions like Disney, or Busch Gardens. Don't settle for a hotel when you and your guests can enjoy a home with a gas grill, multiple patios, large kitchen/family room, a large 4K TV and a private jacuzzi/pool with gas heater *option. It's a perfect place for creating family memories or getting together with old friends.

Guest favourite

Home in Holiday

4.89 out of 5 average rating, 121 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.

Guest favourite

Guest suite in Hudson

4.91 out of 5 average rating, 157 reviews

UVlite sanitized guest suite w/private entrance.

Our 300 square foot guest suite is good for couples and solo adventurers. It offers many amenities for a small space. Step outside to enjoy the patio, pool and gazebo! Great location for those wanting to experience Florida's nature coast, but still be close enough to everything the Tampa Bay area has to offer at a reasonable price. For the safety of our guests, in addition to extensive cleaning and disinfection I am also using a UV/ozone sanitizing light before guests arrive.

Guest favourite

Tiny home in Dunedin

4.95 out of 5 average rating, 110 reviews

Cozy 1 bedroom tiny home with pool "Shelly"

Gorgeous newly built luxury tiny home in the heart of downtown Dunedin. This charming 1 bedroom 1 bath home is has everything you need for a perfect stay in our perfect little town. Only steps away from all the best restaurants, breweries, shops and activities in Dunedin. Dunedin was voted one of the best walking towns in America. Just a short drive to beaches including Honeymoon Island and Clearwater Beach. If you don’t feel like driving you can just relax in the pool.