Holiday rentals with a pool in Hillsborough County

Downtown Tampa Pool House! Walk to Armature Works!

Location! Location! Enjoy Tampa at this modern brand new remodeled POOL HOUSE with the BEST LOCATION & with POOL access! SAFE & EASY location in downtown. Come Experience events, food, festivals & nightlife only 1 block from #1 destination, Armature Works- a famous destination for food, fine dining, events, & fun! Enjoy a quiet downtown getaway to enjoy the pool, biking, paddle board or walk the beautiful Riverwalk.Full kitchen! (* We had NO Damage from Hurricane and home is Not in Flood Zone).

The Jungalow SOHO - Pool/Hot Tub

The Jungalow is the ultimate urban oasis. Enjoy the luxuries of the home or venture out to local attractions like the iconic Bayshore Boulevard, Historic Hyde Park, SOHO, Downtown and more. This home was designed with comfort and convenience in mind. Fully equipped with a smart tv, high-speed WIFI, pool and hot tub - this place is paradise. Central to the action - walk to unique rooftop bars, restaurants and shops or Uber to local attractions like Water Street, Amalie Arena, and the Riverwalk.

The T and C Club

Welcome to The T and C Club! A featured home for the Make-A-Wish Foundation. Located 6 miles from the Tampa Airport, 7 miles from Raymond James Stadium and only 15 miles from award winning Clearwater Beach, this home is convenient as it gets. Completely refurbished, there is plenty of space to sleep 10 individuals comfortably, dining table for 10, a large resort-like backyard, saltwater pool, propane grill and all the fun you can imagine. This will truly be a case of you won’t want to leave!

PondView/Pool/Pickleball/Dryer/Washer/Ground Floor

Pond View ground floor Condo located in within minutes of Tampa Bay's main attractions: Bush Gardens, Hard Rock Cafe and Casino, Tampa Aquarium, Top Golf, Ybor City, Convention Center, I FLY and shopping malls. Condo has a large Resort Style pool, Keyless entry, washer/dryer in the unit and owner on site for if needed. Pickleball, Tennis court, Volleyball, Disc Golf and 24/7 Gym also available. Relaxing community with several ponds and trails to be explored near the unit. FUN/SUN/Business

Beach Front Madeira Beach

PLEASE NOTE: SEVERAL UNITS UNDER CONSTRUCTION in the building. Expected completion by May 31. Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away. The condo is walking distance to shopping, banking and many restaurants and bars.

TIKI Bar+SAUNA+HOT Tub+Heated POOL! 2 KING beds!

If you like pops of color, modern decor a FREE HEATED pool seasonally Oct 15-April 15 (80-85 degrees) HOT TUB , RARE SAUNA, TIKI BAR fire pit and everything new then this house is for you! BRAND NEW HOT TUB installed 4/2025!!! Very Close to shopping and beaches perfect dedicated vacation home! We are family owned and operated and dedicated to you and your vacation experience. Message me if you have any questions! SUPER FAST WIFI 753Mbps - (1 G if you plug into modem) verified by Airbnb

Elegant 5BR Historic Gem w/ pool, walk to Bayshore

New for 2026– Luxury Redesign in South Tampa! This 5 bedroom, 3.5 bath, 1923 home blends historic charm with a brand new upscale interior. Perfectly located just 2 blocks from Bayshore Blvd and Hyde Park, and minutes from Downtown, Riverwalk, and UT. Enjoy memory foam beds, organic cotton linens, 2 King suites, 2 California King bedrooms, 2 twins, custom sofas, designer finishes, and thoughtful touches throughout. A refined, comfortable base in Tampa’s most walkable, sought-after area.

Island Oak

This private vacation rental is a Second floor 1 bedroom apartment is newly furnished, professionally decorated and equipped with all the conveniences of home. Island Oak joins 4 other popular vacation rentals within the Grove Keeper Collective compound. This upper unit has a balcony off the bedroom which looks into a 175 year old oak that provides a tree house effect. We hope you come and enjoy this new addition to Grove Keeper Collective. All our units are non smoking and vaping.

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.

Still Waters Townhome, Sunrise and Sunset Views

Elegant home with 4 balconies, 2 overlooking water. Sunset and sunrise views. Gourmet kitchen, granite countertops, cooktop range, stainless steel appliances. Coffee maker, tea kettle, Nutra-bullet, toaster and more. Each room has a large flat screen smart TV. Bright, modern, immaculate. Wireless internet, Ethernet and Netflix. Washer and dryer on main level. Five minute walk to white sand private beach, complimentary umbrella and chairs. No smoking, no pets, no events.

Luxury Stay • Hot Tub & Heated Pool • Fenced Yard!

Explore the charm of this three-bedroom, two-bathroom bungalow – a luxurious haven where style meets relaxation. Enjoy moments of tranquility by the spa and screened pool, complete with inviting swim-up barstools, or unwind in the indulgent hot tub accommodating up to eight guests. Step into the serene outdoor oasis, adorned with elegant furnishings against the picturesque backdrop of a fenced backyard. Your getaway awaits, conveniently situated near the city's premier attractions.

Honeymoon Luxury Residence with Heated Pool &Sauna

Heated pool, features European-designed interiors, sauna, 100" theater, latest Xbox, gym, and smart TVs in every bedroom. Chef’s kitchen, dining for 12 ideal for celebrations, outdoor gazebo with fireplace & innovative grill, lush tropical landscaping and breathtaking sunset views. Easy access to beaches, marinas, Dunedin, Tarpon Springs, and Clearwater dining & nightlife. Safe, prestigious neighborhood — perfect for family fun or romantic escapes.