
Holiday rentals with a pool in Pinellas County
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Top-rated rentals with a pool in Pinellas County
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Quiet 3 BD Large Heated Pool & Terrasse-5 mn Beach
Unwind and relax while staying at our freshly renovated Floridian nest! Pretend you are lost in our tropical garden while diving in the pool, take some time for yourself on the covered patio directly facing the blue water and the vivid green of the palm trees. Just breathe, your favorite meal smells good on the grill and your family is enjoying the large TV in the comfortable open space with high ceilings! Enjoy the sea, you are a 5 min drive from the beach and close to everything. Feels good!
4.89 out of 5 average rating, 304 reviews
Best Celebration - Heated Pool - Hot Tub - Arcade
🌴 𝐇𝐨𝐮𝐬𝐞 𝐨𝐟 𝐏𝐚𝐥𝐦𝐬 | 𝐘𝐨𝐮𝐫 𝐏𝐫𝐢𝐯𝐚𝐭𝐞 𝐅𝐥𝐨𝐫𝐢𝐝𝐚 𝐏𝐚𝐫𝐚𝐝𝐢𝐬𝐞 ☀️ Escape to a stylish tropical retreat perfectly located near Florida’s best beaches, attractions, shopping, and dining. Ideal for families, groups, or a relaxing getaway, House of Palms offers comfort, privacy, and everything you need for an unforgettable Florida stay. 📍 5 mins – Shopping & dining 🏖 15 mins – Gulf beaches 🌊 20 mins – Clearwater 🌆 25 mins – Downtown St. Pete ✈️ 30 mins – Tampa Airport
4.99 out of 5 average rating, 126 reviews
Heated Pool! Huge Walk In Shower! 5 min to beach!
Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!
4.95 out of 5 average rating, 158 reviews
Private Beachfront 2BR BUNGALOW*POOL*PETS ok
DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows share heated pool
4.97 out of 5 average rating, 206 reviews
Palm Oasis | Heated Pool | Near Beaches
Have fun with the family or just a friend getaway at this stylish cozy POOL home. This newly remodeled 3-bedroom 2-bath home, centrally located between Clearwater and St. Petersburg and a 30 min drive to Tampa to visit all the local attractions. Very close to plenty of restaurants, shopping, and Beaches. This home has everything needed from quality mattresses to kitchen essentials and “Smart TV’s” in every room, very close to shopping, restaurants, movies, Walmart, etc. “Must be 21 to book”.
4.97 out of 5 average rating, 179 reviews
Amazing views on beachfront
This spacious upper-floor, 3-bedroom condo hotel suite offers views of the Gulf of Mexico from your private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the water of the Gulf of Mexico. Each suite can accommodate 10 people, with 3 bedrooms, 2 of them with a King bed in each bedroom and the third with 2 Queen beds, each of them with their own ensuite bathroom, in total 3 1/2 bathrooms, also a comfortable full-sized sofa bed in the living room.
4.91 out of 5 average rating, 488 reviews
Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade
Welcome to Clearwater Tranquility- Our unique space offers endless amenities and fun! With over 5000sq ft there's room for the whole family to enjoy. Most rooms have a view of the yard &pool! Inside includes a movie theatre, 3 dining spaces, 2 living rooms, 2 primary bedrooms, game room, yoga studio,arcade games, home gym/sauna and a wet bar to make your favorite cocktails or juices. Outside presents an Olympic sized swimming pool, pickle ball, mini golf, outside dining, fire pit &more
4.93 out of 5 average rating, 121 reviews
Beautiful Tampa Bay Pool Home Near Gulf Beaches
A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.
5.0 out of 5 average rating, 229 reviews
Tootsie’s Beachside Retreat-New Heated Pool
LUXURY SALTWATER HEATED POOL HOME! JUST 1.5 MILES TO BEAUTIFUL REDINGTON BEACH. AMAZING REMODELED HOME WITH HIGH END FINISHES LOCATED ON 1/2 ACRE LOT. BRAND NEW CUSTOM POOL WITH PEBBLETECH FINISH AND BAJA SHELF. BEAUTIFUL WHITE SAND BEACHES ONLY 1.5 MILE RIDE! 5 MIN. FROM: 3 COFFEE SHOPS,OUTSIDE MALL WITH SHOPPING, RESTAURANTS AND MOVIES. HOUSE IS ON RARE 1/2 ACRE PROPERTY IN UPSCALE NEIGHBORHOOD. RENOVATED WITH HIGH END FURNITURE AND FIXTURES, SAMSUNG 4K LED T.V.’S IN EVERY ROOM.
4.98 out of 5 average rating, 198 reviews
Putt Putt! | 3 bed | Large Pool | Private Yard
Welcome to our Coastal Boho Oasis with a pool and a fenced in large backyard, just a short 12-minute drive from the pristine shores of Indian Rocks Beach! Step into a world of serenity and style in this newly renovated coastal retreat that perfectly blends modern comfort with bohemian vibes. This home is furnished with all of your family’s needs, from a pizza cutter to a pack and play. Come, enjoy and relax. The spacious backyard includes a fire pit and lounge chairs around the pool
4.85 out of 5 average rating, 103 reviews
Hibernate in our Bear Creek Home
This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.
4.91 out of 5 average rating, 190 reviews
Specious home W/ Heated Pool ! ! ! Great Location.
Cozy, spacious home 🏡 w/ heated swimming 🏊♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's. The big back patio has a swimming 🏊♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa
4.98 out of 5 average rating, 237 reviewsPopular amenities for Pinellas County rentals with a pool
House rentals with a pool

This is your Florida home!
4.97 out of 5 average rating, 105 reviews
Cozy Stylish Home w/ Heated Pool & Big Parking
4.95 out of 5 average rating, 195 reviews
Splash House - Relaxation Haven/Private Pool
4.92 out of 5 average rating, 132 reviews
Swim-Out Bedrooms, Waterfall pool, Peace Place
4.92 out of 5 average rating, 171 reviews
Sundaze |Fully Stocked-PS5-EV Charger-2MI to Beach
4.98 out of 5 average rating, 104 reviews
Pelican House, Game Room, Pool, 5 min to Beach
4.87 out of 5 average rating, 162 reviews
Stunning Lakefront-King bed - 10 min to beaches
4.91 out of 5 average rating, 184 reviews
Providence Cove | Heated Salt Pool • Sleeps 12
4.93 out of 5 average rating, 14 reviewsApartment rentals with a pool

Beachfront Condo with Centerline Sunsets
4.94 out of 5 average rating, 172 reviews
Upgraded 3 Bed, 3 Bath Corner Water Front Condo!
4.98 out of 5 average rating, 182 reviews
Rincón Divino MB 2 Balconies, Ocean & Marina Views
4.99 out of 5 average rating, 243 reviews
Spacious Key West Retreat, Fun 2 BR, Resort Pool
4.97 out of 5 average rating, 155 reviews
BEACHFRONT Condo - Belleair Beach Club - RENOVATED
4.72 out of 5 average rating, 548 reviews
Steps to beach with Marina Sunsets – 3 -Bed condo
4.84 out of 5 average rating, 131 reviews
Beach Place Bliss on Madeira Beach by John's Pass
4.87 out of 5 average rating, 113 reviews
Beach Front complex! Shortest walk to Johns Pass!
4.79 out of 5 average rating, 178 reviewsOther holiday rentals with a pool

Tiki House •Sleeps 10 •Walk to Beach + Heated Pool
4.9 out of 5 average rating, 128 reviews
Tortuga Bleu Vacation Retreat
New place to stay
Largo Palms Duplex-2BR/2BA + Heated POOL Unit B
4.98 out of 5 average rating, 53 reviews
6 King Suites Pool + Game Room Oasis Near Beaches
5.0 out of 5 average rating, 9 reviews
Near Beach • Heated Pool • Game Room • Theater
4.6 out of 5 average rating, 5 reviews
Blue Sky | 8PPL | Clearwater | Pool | Pet Friendly
4.9 out of 5 average rating, 96 reviews
Clearwater Pool Oasis|3 BR|2 King Beds|Near Beach
4.86 out of 5 average rating, 7 reviews
Cozy pool home near the beaches
4.96 out of 5 average rating, 23 reviewsDestinations to explore
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