Vacation rentals with a pool in Charlotte Harbor

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Charlotte Harbor

  • Total vacation rentals

    Explore 50 vacation rentals in Charlotte Harbor

  • Nightly prices starting at

    Charlotte Harbor vacation rentals start at $69 CAD per night before taxes and fees

  • Verified guest reviews

    Over 670 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Charlotte Harbor vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Charlotte Harbor rentals

  • 4.8 Average rating

    Charlotte Harbor stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Charlotte Harbor

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favourite
A private heated pool area features clear water surrounded by comfortable seating and vibrant blue umbrellas. A large pink flamingo float is visible in the water, alongside other colorful poolside furnishings. Lush greenery is present in the background, enhancing the outdoor atmosphere.
Home in Port Charlotte
5.0 out of 5 average rating, 103 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

Top guest favourite
Home in Port Charlotte
4.96 out of 5 average rating, 161 reviews

Big Pool+Beautiful Sunsets+Private Yard+Outdoor tv

Private & peaceful resort style outdoor space + oversized solar heated pool creates a perfect vacation oasis. Covered lanai = shade. BBQ & watch your favorite sports on 55” outdoor tv. Walk the golf cart paths, swim laps, get a tan, read a book, play music & games, sip on tropical drinks & float all your cares away in privacy. Gorgeous sunsets overlooking a golf course setting. Carefree outdoor living at its best. ~ Within a few miles of groceries, shopping, dining, bars & downtown Punta Gorda.

Top guest favourite
A covered outdoor space features cozy seating around a fire pit. String lights illuminate the area, creating a warm ambiance. In the background, an inviting above-ground pool is set against a lush garden landscape, showcasing tropical plants and trees.
Home in Punta Gorda
4.96 out of 5 average rating, 280 reviews

Tropical getaway Pool and tiki bar

1)Beautiful newer build house on 2 acres 1800sq/ft with 3 BR and 2 bath sleeps up to 8. 2)Has a large above ground pool 18' x 33' and a large fish pond and outdoor bar/BBQ and tropical landscape parking for 4 cars. 3)15mins drive from downtown Punta Gorda with lots of great restaurants little shops and bars with live music and much more, 7mins drive closest store winn-dixie. 4)10 mins drive to Punta Gorda airport. Located in a peaceful neighborhood with large oak trees on a dead end street.

Guest favourite
A lush green landscape is framed by trees, with a view of calm waters in the background. A wooden dock extends into the water, inviting potential relaxation and observation of local wildlife. The setting sun casts gentle shadows over the manicured lawn.
Home in Port Charlotte
4.85 out of 5 average rating, 237 reviews

Peaceful Port Charlotte 2Bd/2Ba on water

Are you ready to unwind with your friends, partner or the entire family? Look no further than the Comfy Conway. It is close to restaurants, beaches, family-friendly activities and peaceful spots to re-energize. Whether here for business or pleasure, your stay will exceed expectations. I take great pride in making sure guests are comfortable and well taken care of. Stay and enjoy the house amenities or venture out to the great amenities offered by the beautiful surrounding Port Charlotte area.

Top guest favourite
Home in Punta Gorda
4.94 out of 5 average rating, 144 reviews

House/ Caribbean Patio, Hot Tub & Tiki Bar.

3900 Rosemary Drive is a pet friendly house with parking for 2 cars. Relax & enjoy your own private get away, outside patio area, tiki bar, sun loungers & hot tub. The open plan apartment has an 80” Peacock enabled TV,. Enjoy Netflix, Amazon Prime or other subscriptions that you have by entering your home’s password & pin information. In the lounge area there’s a 2 seater theatre style adjustable settee & a small dining table/ working area with Wi-Fi access and a fully equipped kitchen.

Guest favourite
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
4.96 out of 5 average rating, 181 reviews

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.

Superhost
Apartment in Charlotte Harbor
4.9 out of 5 average rating, 10 reviews

Sweet Sunsets

excellent neighborhood, 2 bedroom, 1 Bathroom with shared pool In Punta Gorda, Florida. adjacent from Peace river, in sight of the sunseekers resort and 2 minute drive downtown Punta Gorda for Farmers Market on Saturdays. Private entrace (front) and direct access to Lanai / pool Whatever your reason to visit, we are here for you and your entire family to enjoy a short or long stay in Beautiful SWFL. ATTENTION SNOW BIRDS!!! Will accept daily, weekend, weekly, or monthly rental stays!

Top guest favourite
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.
Home in Port Charlotte
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.

Guest favourite
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.
Home in Port Charlotte
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.

Top guest favourite
An inviting swimming pool is surrounded by a screened lanai, providing a serene setting. Comfortable seating is arranged beneath a wooden ceiling adorned with a ceiling fan. Lush greenery is visible through the mesh, enhancing the tranquil atmosphere of the outdoor space.
Home in Punta Gorda
4.97 out of 5 average rating, 37 reviews

The Coastal Palm Cottage

Discover the charm and walkable beauty of Punta Gorda’s historic district from this inviting 2-bedroom, 2-bath home. Perfectly situated just steps away from scenic waterfront parks, vibrant restaurants, and unique local shops, you’ll have the best of Punta Gorda right at your doorstep. Whether you’re planning a quick weekend escape or a longer Florida retreat, this home offers the ideal blend of location, comfort, and authentic coastal charm.

Top guest favourite
Villa in Charlotte Harbor
5.0 out of 5 average rating, 39 reviews

Luxurious Mangoe 4 bed 2 bath, heated pool & spa

Plan your Florida retreat to this brand new 4-bedroom, 2-bathroom Port Charlotte home. Visit the Fishermen's Village, tan at the nearby beaches and relax poolside in the private yard. With enough space to sleep 8, this luxurious 2100 square-foot vacation rental boasts 4 Smart TVs, a caged saltwater pool and hot tub and a pool table that also changes into air hockey. Parking in the garage available.

Top guest favourite
A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.
Island in Sarasota
4.98 out of 5 average rating, 367 reviews

Last MIN AUG Sarasota #1 Luxury Villa! PRIV BEACH!

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Popular amenities for Charlotte Harbor rentals with a pool

When is the best time to visit Charlotte Harbor?

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