Holiday rentals with a pool in Pinellas County

4.97 out of 5 average rating, 159 reviews

The Ultimate Vacation Pool Home w/Tiki and Cottage

We've set the stage for a first-class vacation experience and a stylish, retro vacation home like no other! Just a 6 minute drive to beaches and 25 mins to Downtown. Phenomenal backyard with HUGE screened-in tiki hut, a huge 32x17' pool + oversized chess board and a pool bar! And last but not least-- a stylish new GUEST COTTAGE with a kitchenette + full bathroom. Perfect for the "guest of honor" or bachelorette accommodations! This home is unique and will exceed your vacation home expectations!

4.95 out of 5 average rating, 123 reviews

Heated Pool & Hot Tub 0.7 mile from Beach

Welcome to our beach house! This is the perfect place for a family vacation or friend getaway. Why We Love The Home: - 0.7 miles from the beach and tons of restaurants/attractions - Resort style backyard with saltwater pool, hot tub, mural for photos and outdoor shower - Quiet and safe neighborhood - Perfect kitchen for entertaining with double ovens Beaches: - 2 min to Indian Shores & Redington Beaches - 10 min to Madeira & Indian Rocks - 20 min to Clearwater & St. Pete Enjoy your stay!

4.88 out of 5 average rating, 271 reviews

Home in Largo

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!

4.98 out of 5 average rating, 172 reviews

Home in Clearwater

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 w/ Sling & Roku. 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

4.96 out of 5 average rating, 130 reviews

Lavish Heated Saltwater Pool Home Mins. to Beach

Paradise awaits in this stunning & pristine 4-BR heated saltwater pool home! Centrally located to many restaurants, stores, and entertainment while only 4 mins from the beach! Private backyard and huge covered patio deck that wraps around the pool. Gracious updates throughout with all of the amenities for a perfect vacation—from the relaxing outdoor lounge space and BBQ grill to the expansive dining table for 12, bars, TV's, firepit, and even an outdoor ping-pong table for hours of family fun!

4.9 out of 5 average rating, 136 reviews

Home in Largo

The Oasis | Heated Pool - Arcades - Mini Golf

Staying at The Oasis is the perfect blend of vacation and home. Every detail was carefully thought out to provide guests two things: comfort and fun. The ULTIMATE vacation awaits you. Whether a group of friends or your family vacation, this home was designed with relaxation AND fun in mind. Located within walking distance to Largo’s beautiful Central Park and a few miles to the beach, you can spend the day exploring the area or truly relax in the resort style, private backyard. BUT! No parties

4.9 out of 5 average rating, 101 reviews

Home in Safety Harbor

Modern Sunny house,pool ,Clw beach, TIA,Dunedin,

Welcome to Safety Harbor house Florida . Close to downtown main street,fun shops,restaurants ,fishing pier water front park and family friendly activities. the home sleeps 6 guests. Has a nice pool and it is great for couples ,solo adventures,business travelers,families with kids .Fully equipped brand new kitchen brand new bedrooms. Wifi TV Alexa. Tampa international airport 15 minutes Clearwater Beach 15 minutes Palm Harbor tarpon springs sunset beach 10 minutes Saint Petersburg 15 minutes.

Bungalow in Indian Shores

4.96 out of 5 average rating, 157 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 + heated pool

4.95 out of 5 average rating, 108 reviews

🍍Beautiful Home Heated POOL 5min to BEACH. 8 ppl🍍

Welcome to your beautiful and spacious rustic coastal-style oasis! Perfect for up to 8 guests. This immaculate updated home is located in Rustic Pines - a quiet area close to Indian Rocks Beach and the new Seminole Shopping Center. Enjoy your private backyard with a pool and luscious landscaping. Walk to shopping, dining, entertainment, and park with trails. 7 min to Largo Golf Course and only 9 min to Splash Harbor Water Park. Every effort has been made to make your vacation memorable!

5 out of 5 average rating, 174 reviews

Home in St. Petersburg

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.

Guest suite in St. Petersburg

4.98 out of 5 average rating, 361 reviews

Cozy Casita in NE St. Petersburg

Our Cozy Casita is located adjacent to the main house in a quiet residential neighborhood with a separate entry and fenced in parking space for our Guests. Enjoy our tropical garden and beautiful pool area. The pool is not heated. Small kitchen with Whirlpool electric stove, microwave and mini-fridge. 40” Samsung Smart HDTV and WIFI. Located within minutes of great restaurants, craft breweries, and local museums. Lots of great outdoor activities along St. Pete’s beautiful waterfront.