Vacation rentals with a pool in Hillsborough County

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.

Family-Friendly: Fun by the Pool & Backyard Games

Our lovely 3BR w/heated-pool sleeps up to 10 if using the study sofa-bed, located in a quiet residential area of Apollo Beach close to local shops & dining. Nearby are the Manatee Viewing Center & the AB Preserve, great for birders or to launch a kayak or hike along the water. Tampa, 25 min. away, offers infinite entertainment opportunities. Along the Keys between Sarasota and St Pete, both 45 min. away, you’ll find some of the US most beautiful beaches. Disney World is just over an hour away!

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!

Single Family Pool Home, Close to Downtown Tampa!

Cypress House is conveniently located to explore the best of Tampa Bay, including Downtown, South Tampa, USF, University of Tampa, other Universities, Busch Gardens, the zoo, aquarium, restaurants, walking distance to University Of Tampa and River Walk, & much more! Situated in an upmarket family-friendly residential neighborhood, this 3 bed/4 full bath luxury single-story home boasts a large outdoor pool, outdoor gas grill, outdoor table, laundry, full kitchen gas stove and oven.

Waterfront Pool Oasis Kayaks, Games & Beach Vibe

Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

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

Luxury design in South Tampa! This 5 bedroom, 3.5 bath, 1923 home blends historic charm with an upscale interior. It’s perfectly located just 2 blocks from Bayshore Blvd, near Hyde Park, and minutes from Downtown, Riverwalk, and UT. Enjoy memory foam beds, organic cotton linens, 2 King suites, 2 California King rooms, 2 twins (with the option to convert to a King) custom sofas, and thoughtful designer finishes. A refined, comfortable base in Tampa’s most walkable, sought-after area.

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

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. 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

Private House with Pool and Cabana

Beautifully updated house with pool and cabana. 3 Bedrooms with queen beds, upscale bedding, TV's in every room, full kitchen and dinning area, BBQ, ready to cook, outdoor pool with cabana with a TV, firepit, gardens, park like backyard. Great for families and business trips. Close to everything, all shopping, 15 minutes to downtown, airport, Hyde Park, International Plaza, Busch Gardens and more. Close to parks, beaches, fishing, Bayshore Blvd, Gandy Bridge.

Villa Paradise

Relax with family in this quiet place to stay. A spacious house to enjoy with family and friends, with a beautiful pool and a large backyard. There is also an outdoor kitchen (only for 6 people). NO MORE THAN 6 PEOPLE. I do not allow events. Guests do not have access to the garage. I live in an apartment in the garage, and I do not have access to the accommodation from anywhere. I am informing you of this for my safety and peace of mind. Thank you.

Tropical 1920s Bungalow with Saltwater Pool

Step into the charm of Old Florida with this 1920s South Tampa bungalow. Nestled beneath grand oak trees on a quiet corner lot in the eclectic Ballast Point neighborhood, this cozy cottage blends vintage charm with modern comfort. This inviting retreat features a tropical backyard oasis, complete with saltwater pool, swaying palms, and cozy outdoor lounging areas - perfect for morning coffee, afternoon sun, or evening swims.

Insta Worthy Retreat -HTD Pool- Arcade Room- Golf

☀️ Looking for a place the whole family/group can enjoy? This centrally located modern home is full of fun and style, with everything you need—from a fully stocked kitchen 🍽️ to beach supplies ⛱️ and more. Enjoy an Insta-worthy space with 5-hole mini golf, giant outdoor games, a heated pool, arcade & board games, and cozy spaces inside and out. 📍 Just 6 miles to the beach and Downtown St. Pete—perfect for your getaway!