Vacation 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 favorite

Condo 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 favorite

Guest suite in Saint Petersburg

4.98 out of 5 average rating, 315 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.

Guest favorite

Condo 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 favorite

Guesthouse in Palm Harbor

4.96 out of 5 average rating, 259 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 favorite

Guest suite in Largo

4.93 out of 5 average rating, 269 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 favorite

Guest suite in Largo

4.97 out of 5 average rating, 343 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 favorite

Home in Indian Rocks Beach

4.98 out of 5 average rating, 119 reviews

Beachfront Bungalow w/ Pool & Hot Tub in IRB

Beach front house with a saltwater pool! This 2 bedroom, two bath house is equipped with a newly renovated kitchen and new appliances. You will have your own private beach access with 2 outdoor showers. The outdoor dining area is perfect for dinner under the sunset. We are stocked with beach chairs, umbrellas, pool/beach toys, & floats. Close to parks, restaurants, & across the street from a small grocery store. Perfect for families or couples looking for a getaway in the sunshine state.

Guest favorite

Guesthouse in St. Petersburg

4.98 out of 5 average rating, 159 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 favorite

Condo in Seminole

4.97 out of 5 average rating, 203 reviews

UPDATEDVacation condo! HEATEDpool3 miles to beach

No damage from Helene or Milton! Wow!! Super value !! 2 bed 1 bath condo - Welcome to Beachway Condos a GATED SAFE private full amenity community featuring a gym, tennis courts, HEATED POOL, grills, located 3 miles to the beautiful gulf beaches. You are close to everything - the Pinellas trail biking/walking is 1/4 mile away, Indian shores beach is the closest beach at 3 miles away. Clearwater/st Pete beaches are 7 miles away. Across the street are grocery stores malls, restaurants

Guest favorite

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.

Guest favorite

Guest suite in Seminole

4.92 out of 5 average rating, 138 reviews

Comfy Pool Suite, Private Entry, King Bd, Beach 1m

Complete privacy and quiet on your closed-off side of the house. One mile to Reddington and Indian Shore Beaches. 10 minute drive to Madeira or Clearwater Beach. Also minutes away from a wide variety of restaurants and shopping. Driveway parking by your private entrance for convenient loading. No stairs, just a 1-step threshold. Comfy king-sized bed. Beach chairs, beach towels, umbrellas available for guest use.

Superhost

Condo in Saint Petersburg

4.86 out of 5 average rating, 434 reviews

Waterfront condo on top floor @ Boca Ciega Resort

Great view of water. Especially beautiful sunsets! Top floor end unit for privacy. Pinellas trail across the street to ride your bike or hike, a beautiful 38 mile trail. Plenty of restaurants nearby and grocery stores. Only 8 min drive to beach. 15 min from downtown St. Pete. Enjoy pool and hot tub overlooking the intercoastal or stay indoors and enjoy puzzles and games.