Holiday rentals with a pool in Pinellas County

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!

Clearwater Gameroom- Pool/Mini golf/Home Theatre

Welcome to Clearwater Hangout- This super unique house was designed to be packed with many amenities. Just 4mi to famous Clearwater Beach! Newly renovated with fresh tiles and quartz counters for a high end trendy design. Inside amenities include- LED vanity, pool tbl/ping pong, wine fridge, dining for 14, and a full transformed game room with a basketball court, Pac-man machine, and a home theatre! Outside is a very private clean space with mini golf, a salt water pool, seating area and firepit

Entire guest home near beach. New floor and shower

Enjoy your spacious private cottage house w/ swimming pool /fire pit in a beautiful tropical garden setting only a short drive to the beaches .We are close to all Pinellas and Hillsborough county attractions. 3 miles to Indian Rocks Beach w/ many restaurants for a locals feel. 5 miles to famous Clearwater Beach for beach fun and Winter the Dolphin. Only 7 miles to idyllic Dunedin downtown for food, live music and breweries. In 25 min you can drive to funky downtown St. Pete or the Tampa airport.

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

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.

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.

*POOL* Bar, Hottub, Central location

Welcome to Pat’s Pub House🌴 Pool, hot tub, & outdoor bar. Peaceful boho vibe. Nature lovers dream! Plants, crystals, & art everywhere. Kids fort with rock wall & sand box. TV you can watch from the pool! Movie projector room with huge comfy couch. Short drive to Florida’s ~BEST~ Beaches, John’s Pass, Downtown St. Pete, & Airports. Central location. 3 bedrooms, 5 beds, 2 baths, dining room, & 2 living rooms. Unique, fun, laidback house. Amazing backyard. Local family owned & operated.

Heated Pool and Spa | 5 min to beach

** This house has no checkout requirements - just take your belongings and close the door on your checkout day. ** Experience the ultimate beach vacation in our stunning 3BR home, boasting a brand-new (Jun 2023), upscale pool for leisurely days under the sun and huge in-ground hot tub for relaxing evenings. The fully-equipped kitchen, thoughtfully arranged, provides all modern amenities. Each bedroom, with its plush bedding, is perfect for relaxation after a day’s activities.

UTOPIA!Heated Pool &Hot Tub 2 master suites w KING

UTOPIA best describes this perfect single story VACATION HOME ! 5 MINUTE DRIVE TO BEACHES!! HUGE AMAZING RESORT SYTLE FREE HEATED POOL with LUXURIOUS PERGOLA, HOT TUB , TIKI BAR and plenty of outdoor seating perfect for soaking up the Florida sun ! Large 3 bedroom 3 bath pool home. Pool heat starts Oct 15 and runs thru april 15 seasonally for FREE( heats 80-85 degrees) large four person hot tub is hot and ready at 101° upon your arrival. No waiting on a hot tub to heat up!