
Holiday rentals with a pool in Pinellas County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Pinellas County
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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

Relax in private Heated pool Family-Friendly comfo
Outdoor Paradise Private 10,000-gallon PebbleTec pool (up to 8 ft deep) Cantina bar for poolside refreshments Teak lounge seating & chaise chairs Weber propane grill + rolling cooler Resort-style umbrellas & lush landscape for sun or shade Fully Equipped Kitchen Stainless steel appliances, cookware & utensils Coffee station fully stocked Air fryer + blender for smoothies & cocktails Unique Octopus Garden dining area Living Room Large ultra-comfy sectional 70” Samsung Smart TV Boa

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach
🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

"Twilight Sands Stud" Private Entrance, Pool, Parking, Keyless Entry
Welcome to our cozy guest suite—where comfort is personal over perfect, and full of charm you won’t find at a hotel. Guests love the thoughtful touches, eclectic decor, cloud-like bed, and the irreplaceable feeling of being at home when you’re far from home. Our home uses one central AC unit. Because Florida is warm and humid year-round, we keep the thermostat at 70°F by day and 67°F at night for proper cooling and comfort. If you prefer more warmth, two space heaters are in the suite closet.

The West Wing with Saltwater Pool
The West Wing is 1 of 3 suites available at our luxury adult only home, sleeping 2 people per room. We can accommodate a total of three couples at a time, so you’re welcome to have your friends join you, it’s a great couples or single getaway! You’ll love the large salt water pool. Out place is quiet, peaceful and very private, hidden from the street. All guests must be listed on the reservation to be on the property. TVs are internet ready, must have their own account and fire stick, etc.

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!
Vibrant 2BR/1Bath home sleeps 8 guests with a magical outdoor space designed to create beautiful memories! A tropical saltwater pool and large covered entertainment area complete with a TV—perfect for relaxing and enjoying a cocktail. The interior is colorfully curated to embody the essence of a vacation! Located just 5 minutes from the beach and 25 minutes to downtown. We have 16 Airbnb homes (family-owned and operated), and we're dedicated to finding the perfect fit for your getaway.

Tootsie’s Beachside Retreat-New Heated Pool
LUXURY SALTWATER HEATED POOL HOME! JUST 1.5 MILES TO BEAUTIFUL REDINGTON BEACH. AMAZING REMODELED HOME WITH HIGH END FINISHES LOCATED ON 1/2 ACRE LOT. BRAND NEW CUSTOM POOL WITH PEBBLETECH FINISH AND BAJA SHELF. BEAUTIFUL WHITE SAND BEACHES ONLY 1.5 MILE RIDE! 5 MIN. FROM: 3 COFFEE SHOPS,OUTSIDE MALL WITH SHOPPING, RESTAURANTS AND MOVIES. HOUSE IS ON RARE 1/2 ACRE PROPERTY IN UPSCALE NEIGHBORHOOD. RENOVATED WITH HIGH END FURNITURE AND FIXTURES, SAMSUNG 4K LED T.V.’S IN EVERY ROOM.

Luxury Beach Cottage | Walk to Dining & Sunset
Escape to paradise at Sunshine Escapes IRB! Welcome to Coco, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem that radiates a whimsical, small-town charm, evoking nostalgic memories of carefree childhood summers by the shore—the Gulf of Mexico beckons just two blocks away, offering pristine, fluffy sands and unforgettable sunsets. As the sister cottage of Mango, Coco invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect getaway awaits!

The Tropical Oasis, w/ Solar Heated Pool and Games
Welcome to your private, tropical escape! Unwind by the solar-heated pool in a screened, mosquito-free lanai. FUN & GAMES: Enjoy Billiards (Pool Table) 🎱, Foosball, Cornhole, board games, and 3 Smart TVs 📺. PRIME LOCATION: Only 5 min 🚗 to Indian Rocks & Bellaire Beach, FL Botanical Garden, and dining. Essentials: 🌞 Heated Swimming Pool (Private!) 🎮 Billiard Table / Foosball Table / Cornhole / Boardgames and more! 🛏️ 4 Queen/Full Beds 🧺 Beach Amenities

🏝🏝Charming Bayfront Condo at Boca Ciega
This lovely waterfront condo located in wonderful Boca Ciega Resort in St. Petersburg, FL has everything you need for an extended stay. Centrally located with great views and amenities. Enjoy the sunset and gorgeous views whether it’s inside while lounging on the sofa or outside on the balcony. It sleeps up to 3 people (one bedroom and a sofa in the living room). Full kitchen, TV in living/bedroom, WiFi, and close proximity to the best beaches Florida has to offer.

SHEEK and Glam- heated pool Updated! 3 mi to beach
UPDATED modern Light and bright colorful condo w FREE HEATED POOL! First floor NO stairs. 2 miles from the beach. Crazy FAST WIFI- at 600mbps !!! Great central location close to 2 malls, restaurants, parks and many local gulf coast beaches. SAFE GATED quiet community has a heated pool, gym, tennis courts and gas grills for you to enjoy. Just bring your beach blanket and swim suit and RELAX! Walking distance to so many stores/restaurants and the Pinellas trail !

Waterfront studio! Heated pool and hottub
Wake up to stunning waterfront views! Unwind in this bright studio overlooking Boca Ciega Bay, sip coffee on your private balcony while watching dolphins. Highlights: • Direct waterfront views from balcony • Heated pool, spa & fitness center overlooking bay • Minutes to Madeira Beach, St. Pete, & War Veterans’ Memorial Park • Cozy king bed • Close to boat rentals, trails, and waterfront dining Perfect for romantic getaway or peaceful solo escape!
Popular amenities for Pinellas County rentals with a pool
House rentals with a pool

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

Beautiful Tampa Bay Pool Home Near Gulf Beaches

Tropical Oasis Retreat w/ Heated Pool

Splash House - Relaxation Haven/Private Pool

Heated Pool | 2BD 2BA | Home near Beaches

Belleair Beach Oasis w/ Heated Pool - 3mi to Beach

Swim-Out Bedrooms, Waterfall pool, Peace Place

Luxury Oasis • Heated Salt Pool • Near Beaches
Apartment rentals with a pool

Relax in a Newly Renovated Beach Front Paradise

COASTAL CHIC! Luxury Apartment with Oceanviews

Newly Reno Luxury Condo 30 Steps to Paradise

Renovated Condo! Across the Street From The Beach

Modern and Cozy Condo 6 Minutes from the Beach !

Boho Beach Condo

Sea La Vie- Studio by the bay!

Tropical Beachfront Penthouse-Beach Cottages
Other holiday rentals with a pool

Luxury Tiny Home 1 Bed - 1 Bath Unit B "Sandy"

Wonderful Condo at Avalon - Fully Renovated

Beachfront Oasis / Pool, Beach Access & Ocean View

Stylish NEW one bedroom condo Clearwater beach

Condo Conveniently located to Clearwater Beach

Heated Pool • Newly Renovated • Close to Beaches

Luxury Pool House

Casa Brisa - Htd. Pool-Unique Bungalows-Hot Tub
Destinations to explore
- Loft rentals Pinellas County
- Resort rentals Pinellas County
- Smoking-friendly rentals Pinellas County
- Rentals with an accessible-height toilet Pinellas County
- Family-friendly rentals Pinellas County
- Private suite rentals Pinellas County
- Bed and breakfasts Pinellas County
- Townhouse rentals Pinellas County
- House rentals Pinellas County
- Villa rentals Pinellas County
- Pet-friendly rentals Pinellas County
- Rentals with a kayak Pinellas County
- Rentals with a cinema Pinellas County
- Waterfront rentals Pinellas County
- Rentals with a fireplace Pinellas County
- Rentals with an EV charger Pinellas County
- Rentals with a hot tub Pinellas County
- Rentals with a patio Pinellas County
- Rentals with lake access Pinellas County
- Rentals with breakfast Pinellas County
- Cottage rentals Pinellas County
- Bungalow rentals Pinellas County
- Luxury rentals Pinellas County
- Rentals with beach access Pinellas County
- Rentals with a washing machine and dryer Pinellas County
- Rentals with a sauna Pinellas County
- Boutique hotels Pinellas County
- Rentals with a firepit Pinellas County
- Tiny house rentals Pinellas County
- Holiday home rentals Pinellas County
- Aparthotel rentals Pinellas County
- Hotel rooms Pinellas County
- Motorhome rentals Pinellas County
- Serviced apartment rentals Pinellas County
- Rentals with outdoor seating Pinellas County
- Guest house rentals Pinellas County
- Fitness-friendly rentals Pinellas County
- Flat rentals Pinellas County
- Beachfront rentals Pinellas County
- Beach apartment rentals Pinellas County
- Rentals with an accessible-height bed Pinellas County
- Apartment rentals Pinellas County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Turtle Beach
- Weeki Wachee Springs
- Coquina Beach
- Dunedin Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park
- Adventure Island
- Gulfport Beach Recreation Area
- Things to do Pinellas County
- Nature and outdoors Pinellas County
- Food and drink Pinellas County
- Art and culture Pinellas County
- Sightseeing Pinellas County
- Tours Pinellas County
- Sports activities Pinellas County
- Things to do Florida
- Food and drink Florida
- Sports activities Florida
- Wellness Florida
- Art and culture Florida
- Sightseeing Florida
- Tours Florida
- Entertainment Florida
- Nature and outdoors Florida
- Things to do United States
- Tours United States
- Food and drink United States
- Sightseeing United States
- Nature and outdoors United States
- Sports activities United States
- Art and culture United States
- Wellness United States
- Entertainment United States




