Holiday rentals with a pool in Port Charlotte

A canalfront area features a serene gazebo surrounded by lush green grass and white pebbles. The vibrant sunset sky adds warmth to the scene, and the private boat dock is visible in the background, enhancing the tranquil outdoor setting.

5.0 out of 5 average rating, 106 reviews

Xanadu|Fishing/ Pool/Dock|Kayaks|Bar/Gazebo/ Kids

Welcome to XANADU Luxury Villa 🌊 your canalfront paradise with a private BOAT DOCK ☀TOP LOCATION📍, close to: beautiful beaches 🏖️ Gasparilla Island, Siesta Key, Englewood! ☀Dock Ideal to FISH 🎣| Deck🎴 ☀BAR🍷 ROOM Dancing Light 🪩 ☀DEDICATED WORKSPACE 💻 ☀GAME🎮 Room /Roblox/Arcades🕹️ ☀Smart TVs in every room📺 ☀HEATED Pool 🏊‍♀️ ☀Fast WIFI📶 ☀Ping Pong Area in Sand 🏓 ☀Fully equipped kitchen🍽️ ☀Pool Table and Games🎱♟️ ☀ Outside dining table😋/Fireplace ☀BBQ🍖Ice Maker🧊 ☀Self check in 🔐 Smart Lock

5.0 out of 5 average rating, 27 reviews

Canal front, gulf access, pool, spa, game room

Welcome to Harbor Breeze Gulfstream, a 3/3 waterfront retreat designed for relaxation, fishing & boating. Perfectly situated just a 5-minute walk from Charlotte Beach Park & Marina, this cute home comfortably accommodates 6 to 9 guests, making it perfect for families, couples, or friends seeking a sun-soaked getaway on Florida’s Gulf Coast and to enjoy of the many amenities such as the BBQ grill, Game Room, Pool, Spa, kayaks & Fire pit. Bring your boat or rent it and get ready for the adventure.

A spacious backyard features a putting green surrounded by artificial turf, creating a vibrant green area. Two lounge chairs provide comfortable seating. Fenced for privacy, the space is enhanced by tropical trees and minimal landscaping, under a clear blue sky.

4.99 out of 5 average rating, 128 reviews

Family Fun Stay • Heated Pool + Putting Green

Less than 30 Minutes away to the ballpark for #Rays and #Braves spring training! Our vacation home is a peaceful oasis, perfect for rest and relaxation in one of the most sought-after neighborhoods in Port Charlotte! Enjoy a relaxing stay in this modern and stylish vacation home which offers the following list of amenities: Wi-Fi, TV Streaming, heated pool, putting green, screened in lanai, beach accessories, equipped kitchen, outdoor grilling space, luxurious king beds and private backyard.

Holiday home in Port Charlotte

Aerial view of a waterfront property featuring a modern single-story house with a red-tiled roof. Surrounding palm trees are visible, and the serene waterway reflects the sunset colors. Lush greenery is present nearby, enhancing the peaceful ambiance of the landscape.

4.91 out of 5 average rating, 100 reviews

Jaw-Dropping Waterfront Sunset Views and Gameroom!

Welcome to SUNSET MANOR! This waterfront property sits on a beautiful and spacious corner lot with all the amenities including a heated pool with a tranquil waterfall feature. The preserve across the way provides the ultimate private oasis. This is one of THE BEST views in all of Charlotte County! The house is located in a beautiful and quiet waterfront community - just a few miles from the beach, Boca Grande, Punta Gorda, Fort Myers, and more. World-class Florida living at your fingertips!

Superhost

The exterior of a single-story home is showcased, featuring a spacious driveway lined with pavers. Lush landscaping is present, including palm trees and colorful flowers. The front entrance is accentuated by a decorative archway and a garage door on the right.

Home in Punta Gorda

4.96 out of 5 average rating, 202 reviews

Seasonal vacation rental with Heated pool

The living room has a 65 " smart TV,wall mounted with a LCD Fireplace below with surround sound- All TV's have Netflix.The bar room has a small refrigerator,pool table and dart board.Outside has a private lanai with Heated pool and a propane firepit.Enjoy the sonos sound with 55" smart TV in the Master bedroom the second bedroom also has a TV. The bar room,also has sonos as well as the lanai.30 minutes from several beaches.The garage will not be available.Home located in a quiet Cul de Sac

4.96 out of 5 average rating, 181 reviews

A pool area is enclosed by a screened patio, featuring a curvilinear pool with clear water. Lounge chairs and a vibrant red umbrella are positioned beside the water. The home’s large windows offer views of the surrounding outdoor space.

Home in North Port

Beautiful & Cozy Pool Villa in Sarasota County, FL

Welcome to our home! It’s our pleasure to host you! Your family & friends will be close to everything when you stay at this centrally-located place: shopping, dining, beaches, entertainment, Warm Mineral Springs, Aquatic Center, etc. This charming house located in a beautiful & quiet neighborhood, tastefully furnished & decorated, fenced for your privacy & perfect for making memories with family & friends. Plenty of amenities to make your stay as comfortable as possible. Great location.

A spacious heated pool features a clear blue water surface, enclosed by a screened cage to keep insects out. A pool ladder leads into the water. Nearby, a colorful pool float and a water slide are visible, with a green grassy yard beyond the enclosure.

4.94 out of 5 average rating, 106 reviews

Heated Pool-Outdoor TV & Bar-Private backyard

SUN BUM offers a heated in-ground pool with Southwest exposure = SUN ALL DAY. Our pool jets create a soothing lazy river effect that gently push you around the pool. Grab a pool floaty and let all your cares melt away. Relax in total peace and tranquility. Our backyard has a tall privacy fence that will give you the solitude you seek. The guys in your group are sure to enjoy the outdoor tv, bar and propane BBQ. Lanai provides relief from the sun. Pool cage provides relief from the bugs.

A spacious home is set on a well-maintained lawn, featuring a white exterior complemented by lush tropical landscaping. Palm trees and shrubs enhance the entrance, while a smooth driveway leads to a two-car garage. The sky is clear and blue, adding to the inviting appearance.

5.0 out of 5 average rating, 105 reviews

Elegant heated pool canal home in very quiet area.

Great location! Bring your dog, bring your boat and enjoy the Florida sun in your heated saltwater swimming pool. Fish off your private dock while watching for dolphins or manatee. You can meet the rest of the opacarophiles who walk to the beach to view the sunset. Relax in the jacuzzi with your favorite beverage. NOTE: Beach is sandy but the water is BRACKISH, not clear. This is mostly a retirement neighborhood. This is NOT a party house and not suitable for unattended children.

4.94 out of 5 average rating, 122 reviews

The entrance features a modern facade with a front door framed by tall windows. Flanking the door are well-maintained shrubs and palm plants. A clean walkway leads to the door, complemented by light-colored stone and decorative gravel.

Home in North Port

Flourish in Florida heated pool & spa

This luxurious modern tropical home is the perfect relaxing vacation rental for the whole family or a group of friends. Stay in to enjoy the pool surrounded by greenery, spending your evenings in the private lit up jacuzzi. Located only 10 minutes to Port Charlotte beach, 15 to well known Warm Mineral springs, 30 minutes from the famous Englewood & Venice beach. The Spacious home is 2 queens, 1 queen&twin bunk, 1 pull out couch in office, living room sofa, 2 Full bathrooms.

An aerial view captures a light blue house with a spacious driveway and manicured lawn, surrounded by lush greenery and a serene canal. The home features a charming front porch and is set within a quiet neighborhood, showcasing the tranquil natural landscape.

4.96 out of 5 average rating, 45 reviews

Peaceful waterfront home

Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in our cocktail pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

A private heated pool is surrounded by a screened lanai, providing a bright and airy space. Comfortable seating options are positioned nearby, along with a few plants adding a natural touch. Sunlight filters through the screen, casting gentle shadows across the deck area.

4.92 out of 5 average rating, 169 reviews

Heated Pool Vacation Getaway

This 3 bedroom, 2 bath house with private heated pool is located in a quiet neighborhood near everything that Southwest Florida has to offer. Minutes from restaurants and grocery stores, a couple of miles from the Port Charlotte Harbor and a short drive to some of the most beautiful beaches, you can truly have it all. Our house offers great wifi, a fully functional kitchen, updated furnishings and a heated pool. Self check-in and out guarantee complete privacy.

4.94 out of 5 average rating, 145 reviews

Luxury Bungalo with Pool in Port Charlotte

Please make yourself at home. Relax in a in ground heated pool. Centrally located in a peaceful neighborhood & close to beaches, parks, golf, entertainment & restaurants. You will find all the comforts you are looking for. Grocery stores like Publix, Aldis, Sprouts & Walmart within 3 miles. Sunseeker Resort 4.2 miles away. Downtown Punta Gorda is 6 miles away. Fisherman’s Village has shopping & restaurants. Port Charlotte Beach Park is 2 miles away.

Popular amenities for Port Charlotte rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area features a comfortable seating arrangement with a view of the pool. A large patio includes a heated pool, while a private dock leads to the canalfront, accented by a striking red Adirondack chair.

4.98 out of 5 average rating, 84 reviews

Villa Joy | Heated Pool • Canal Front • Dock

5.0 out of 5 average rating, 25 reviews

Heated Pool | Waterfront Home | Coastal Escape

5.0 out of 5 average rating, 11 reviews

The Sunrise Seeker | Waterfront | Heated Pool |Spa

4.92 out of 5 average rating, 25 reviews

Private Heat Pool. Gazebo, canal kayaks free pets

5.0 out of 5 average rating, 13 reviews

Spacious Beach House with Ocean Access

5.0 out of 5 average rating, 36 reviews

Home in South Gulf Cove

Spa, Heated Pool, Tropical Waterfront Near Beach

5.0 out of 5 average rating, 23 reviews

Heated Pool, Hot Tub, Fire Pit + RV/Boat Parking

4.98 out of 5 average rating, 54 reviews

An aerial view reveals a spacious home situated near the waterfront, surrounded by lush greenery. A dock extends into the calm water, complemented by the serene landscape of mangroves in the distance. The sky is bright with scattered clouds, enhancing the scenic backdrop.

Home in Punta Gorda

Hidden Gem in Punta Gorda

Apartment rentals with a pool

A beachfront property is depicted, featuring a two-story structure with a spacious porch. Surrounding landscape includes sand and lush greenery, leading to the waves of the Gulf of Mexico. Sunbathers are seen in the distance, enjoying the beach atmosphere.

4.91 out of 5 average rating, 234 reviews

Manasota Key

A two-story building is shown, featuring a wraparound porch adorned with railings and chairs. Lush green foliage leads to a sandy path, inviting access to the beach. The sky is partly cloudy, enhancing the coastal ambiance of the location.

4.96 out of 5 average rating, 137 reviews

Sunset Beach

An aerial view shows a heated pool surrounded by tropical landscaping. Lounge chairs are positioned around the pool, with a shaded seating area featuring a table and chairs visible. Lush palm trees and greenery frame the space, enhancing the serene atmosphere.

4.94 out of 5 average rating, 101 reviews

Steps to Water! Beach to Bay, Penthouse!

4.97 out of 5 average rating, 135 reviews

Studio, pool, private beach, boat dock shark teeth

4.8 out of 5 average rating, 173 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

4.87 out of 5 average rating, 191 reviews

Apartment in Nokomis

Private Beachside Kitchenette

Superhost

Apartment in Venice

4.96 out of 5 average rating, 111 reviews

Vintage Villa 35 | Steps to Beach | Pool

A bright living area features two light-colored sofas adorned with decorative pillows. A coffee table with a glass top sits between them, complemented by decorative items. Natural light fills the space through multiple windows, enhancing the relaxed coastal ambiance.

4.9 out of 5 average rating, 152 reviews

A Beautiful Sunset Awaits - Steps to Beach

Other holiday rentals with a pool

4.96 out of 5 average rating, 24 reviews

Poolside Fun at The Caddy

Home in Punta Gorda Isles

4.94 out of 5 average rating, 63 reviews

Dog Friendly | Walk to Fishermen’s Village • Pool

4.96 out of 5 average rating, 25 reviews

Home in Arcadia

Manoir Folie à Deux – Tuscan Countryside

4.95 out of 5 average rating, 64 reviews

Marina/Heated Pool/Hot tub/Canal/Game room/14PPL+

Villa in Charlotte Harbor

5.0 out of 5 average rating, 39 reviews

Luxurious Mangoe 4 bed 2 bath, heated pool & spa

5.0 out of 5 average rating, 20 reviews

Happy Tarpon |10 PPL| Deck & Pool |Games |Fire Pit

A serene outdoor space featuring a fenced pool surrounded by lounge chairs and umbrellas. Tropical plants and grass enhance the area, while palm trees provide shade. The backyard offers a peaceful retreat, ideal for relaxation under the sun.

4.8 out of 5 average rating, 81 reviews

Oasis with pool in the middle of West Coast, FL

An aerial view showcases the home surrounded by lush greenery and a well-manicured yard. The property is located along a canal, with a private dock visible. The peaceful neighborhood is highlighted by tree-lined streets and open spaces, contributing to a serene atmosphere.