Holiday rentals with a pool in Pinellas County

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Top-rated rentals with a pool in Pinellas County

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

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Guest favourite

Apartment in Indian Shores

4.99 out of 5 average rating, 108 reviews

Tropical Beachfront Penthouse-Beach Cottages II

Welcome to this spacious top floor oceanfront condo, located in beautiful Indian Shores, between Clearwater & St Pete Beach on the crystal clear waters of the Gulf of Mexico. This exquisite condo with magnificent oceanfront views is just fabulous! We've taken great care to ensure everything about this vacation home is remarkable & tastefully complimented with King & Queen size beds, full kitchen/dining/bar area, Free High Speed Internet, Premium TV, Garage Parking, Private Beach, and Pool/Spa.

Guest favourite

Guest suite in Saint Petersburg

4.98 out of 5 average rating, 309 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/jacuzzi are 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.

Superhost

Guest house in St. Petersburg

4.9 out of 5 average rating, 477 reviews

Private Guest House sleeps 4 w/POOL & near beach!

This adorable pool house is light and airy with plenty of room for 4. There’s a king size bed, queen pullout sofa, dining area, efficiency kitchen perfect for light cooking, oversized closet and a newly remodeled bathroom. Guests have private entrance with small yard and patio of their own, and are encouraged to use the pool and backyard anytime, which we enjoy along with our sweet dogs, Frog and Bella. 3 miles from beach and downtown, lots of restaurants and shopping centers within 1.5 miles.

Guest favourite

Apartment in Indian Shores

4.96 out of 5 average rating, 115 reviews

"Sunsational" Indian Shores Getaway!

Updated studio perfect for your beach vacation! Great location with the Intercoastal Waterway in your backyard & access to the public beach right across the street in front! When you’re not soaking up the sun & sand, you’ll appreciate the community amenities which include the second largest pool (not heated) on all the barrier islands, boat slips, picnic tables/bbq area, and shuffleboard. The second floor studio is comfortable and equipped with everything you’ll need…just bring your sunscreen!

Guest favourite

Guest suite in Largo

4.93 out of 5 average rating, 266 reviews

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

Welcome to your private Studio located 10 minutes from Indian Rocks Beach FL. Come stay with us and dip your toes in the warm white sugar sands of the Gulf of Mexico. Our beautiful cozy studio has private parking, entrance and keyless entry, cozy cal king bed, on suite bath/shower w/bidet, sweet retro kitchenette including mini fridge/freezer, microwave and Keurig coffee/tea express. Beat the crowd, book your stay, relax at the best beaches in the country or explore Tampa Bay or St.Pete!

Guest favourite

Guest suite in Largo

4.97 out of 5 average rating, 333 reviews

Private Pool, Jacuzzi, Walk to Beach.

This Guest Suite is a large Studio Apt(360 sq ft) attached to our home. It has a private entrance, a large bath, large bedroom with pool view and private deck. Also includes a kitchenette with full size fridge, toaster, coffee maker and microwave. No Stove. Complimentary breakfast snacks including Coffee, tea and biscuits. Relax on the deck and watch the birds on the bird feeder or grab our bikes, beach chairs and head to the beach. Grill available. Please read house rules before booking.

Guest favourite

Apartment in Redington Beach

4.8 out of 5 average rating, 198 reviews

Gulf view Condo with pool in Clearwater/St. Pete

Located between Clearwater Beach & St. Pete Beach, this fully furnished Studio features a full kitchen with a full-sized stainless steel refrigerator and dishwasher, granite countertop, microwave, kitchenware, a Queen bed, a queen size sleeper sofa, closet space, and new AC. This quaint 35-unit resort condo offers a heated pool with tables, lounge chairs and gas grill within a smoke-free tropical courtyard. Just step out the front door for a view of the gulf & 3 mins. walk to the beach.

Guest favourite

Apartment in St. Petersburg

4.96 out of 5 average rating, 224 reviews

Waterfront condo! Mins to beach! Great location!

This unit has been completely updated! Very modern, new furniture, large screen TV's, a gorgeous view from your private balcony of the Bay! This condo in St. Petersburg is close to all amenities including many restaurants, shopping... lots to do! 6 minute drive to Madeira Beach! Close to fishing including deep sea. 1-bedroom, condo sleeps 2 (plus up to 2 small children on a blow up mattress). A quiet, private balcony, pool & hot tub (CLOSED UNTIL FURTHER NOTICE) and fitness center.

Guest favourite

Guest house in St. Petersburg

4.98 out of 5 average rating, 155 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL NEW HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. DEI honored here. Come & enjoy!

Guest favourite

Guest house in St. Petersburg

4.9 out of 5 average rating, 132 reviews

Gorgeous 1 bedroom guest space with pool

The Old Grover House welcomes you. Enjoy your one-bedroom unit on wheels (LARGE CAMPER WITH SLIDES) with a full kitchen, bathroom, pull-out couch, fireplace, dual A/C unit, WiFi, and amenities( such as sodas, bottled water, coffee & tea). There is a garden with a pool—many places to relax and enjoy your complimentary continental breakfast. Friendly dogs under 20 lbs are welcome in this 3-dog home. We also have three cats that live outside. There is space for two cars to park.

Guest favourite

Rental unit in Largo

4.98 out of 5 average rating, 134 reviews

LOVELY & SUNNY Condo 6 Minutes from the Beach!

You will love this first-floor unit! Bright, spacious and updated condo just a 6-minute drive to Indian Rocks Beach! Also nearby are various parks with trails and picturesque greenery. As well as close by there are several restaurants, grocery stores. Beautiful and interesting cities such as Clearwater, Tampa and St. Pete are just a stone's throw away, this is a paradise for everyone! This complex has a pool, gas BBQ for grilling, laundromat and free parking.

Guest favourite

Apartment in Indian Shores

4.92 out of 5 average rating, 108 reviews

Sunny 'n cozy condo, just footsteps from the beach

Need an AFK Getaway? Barefoot Beach Resort is ideally located in the heart of Indian Shores where you're just footsteps away from the beautiful Gulf of Mexico and its gorgeous powder white sandy beaches. Relax, unwind and enjoy a breathtakingly tranquil beach vacation away from large crowds and fast paced days. Start your day with a leisurely walk along the beach, and you won’t want to miss the stunning Florida sunset to top off your day.