Holiday rentals with a pool in Charlotte Harbor

4.89 out of 5 average rating, 9 reviews

Quiet Neighborhood ~ Waterfront Heated Pool!

Welcome to our elegant waterfront home in beautiful Port Charlotte! Nestled along the sparkling waters, this stunning property offers the perfect blend of luxury, comfort, and picturesque views. Cool off with the covered patio and full-size pool. Soak in some sunshine on the hammock. Enjoy the crackle of the firepit under the stars. With its many updates and thoughtful design, this vacation home has been carefully curated for making memories, and providing an unforgettable vacation experience.

The exterior of the home is shown during dusk, featuring a simple, modern design with a prominent chevron pattern on the facade. A well-kept lawn surrounds the house, complemented by palm trees and landscaped areas. A vehicle is parked in the driveway.

5 out of 5 average rating, 41 reviews

Port Charlotte Retreat

Welcome to this delightful home in Port Charlotte near Punta Gorda in a quiet neighborhood yet close to stores and restaurants. This lovely property features 2 bedrooms. The master has a king bed with walk in closet and on suite bath. The second bedroom has a queen bed and nearby bathroom. Split design with the living space between the bedrooms. There is also a queen size sofa sleeper in the living room. Pool and Lanai are fully screened with a BBQ available. Free WiFi and parking, Roku TV.Go

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.

4.95 out of 5 average rating, 260 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.

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.

4.95 out of 5 average rating, 187 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

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.

4.85 out of 5 average rating, 229 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.

A private heated pool is surrounded by a patio with lounge chairs and colorful tropical plants. The pool features a gentle curve and is complemented by a backdrop of a serene home and clear blue sky.

4.86 out of 5 average rating, 111 reviews

Blissful Waterfront Haven with Heated Pool

Serene Pet-Friendly Waterfront Retreat with Heated Pool near the Peace River. Enjoy a fresh water canal view, relax in the heated pool, and embrace the tranquility of Port Charlotte. Perfect for nature lovers and seekers of relaxation. Book now! *Heated Pool* OPTIONAL $29 per day for the pool. This will be paid on the check in date. Please keep in mind that the pool heater runs 8 hours per day. It may cool down at night and morning. *Gas grill available, guests responsible for propane*

4.9 out of 5 average rating, 126 reviews

Fun Luxury Stay: Mini Golf, Pool, Bowling

Escape to a private family paradise with a pool, spacious play yard with minigolf, hopscotch, tic tac toe and garden views for unique outdoor relaxation, BBQs, and creating unforgettable memories. Splash, play and unwind in crystal clear waters while laughter fills the air. Step inside the well designed luxurious interior which provides utmost comfort and is equipped with all essentials and more. Your adventure awaits in this dreamy retreat. This private home is 15min from Beach Park

A serene sunset is captured over the pool area, with vibrant purple and orange hues filling the sky. Illuminated palm-style lights adorn the seating area, creating a playful ambiance. Comfortable seating is arranged with colorful cushions, inviting relaxation amidst the peaceful backdrop.

4.97 out of 5 average rating, 140 reviews

Big Pool~Outdoor TV~Private Oasis~Gorgeous Sunsets

Big heated pool is private from neighbors. Full sun on the pool from noon to sunset. Covered lanai provides relief from the sun. BBQ & watch football on outdoor tv while the kids swim & play. Enjoy beautiful sunsets overlooking a peaceful park-like setting. Walk the golf cart paths, work on your tan, read a book, play music, sip on tropical drinks & float all your cares away. Have your morning coffee outside & listen to the birds sing. Outdoor living is what it’s all about here.

A stylish pool area is illuminated by soft lighting at night, featuring two large red umbrellas over submerged seating. Calm waters reflect the surroundings, while palm trees frame the view, creating a serene atmosphere by the water's edge.

4.95 out of 5 average rating, 59 reviews

Amazing Peace River Views

House is a 2 bed, 2 bath layout. The Master bed is a king bed and the guest bedroom is a queen. Both bedrooms have walks in closets with easy and convenient shelving and built in hampers. The laundry is stocked with liquid soap and fragrance free powder with fast efficient machines. There are speakers in the house, lanai and pergola. You will be able to control them via your phone. There is a desk work area with extra monitor for laptops and a printer for your use.

An enclosed pool area features a spacious swimming pool, flanked by a brick patio and lush greenery. The pool is set under a protective screen, allowing for ample natural light to filter through, while comfortable seating is arranged nearby for relaxation.

4.91 out of 5 average rating, 32 reviews

Pool & Outdoor Patio Miles from Charlotte Harbor

Escape to Zen Hideaway, a luxurious, modern retreat designed with your well-being in mind. This private oasis features an enclosed serene pool, outdoor dining area, outdoor shower and a custom chef’s kitchen for those who love to cook, wine and dine. Walking distance to Port Charlotte Beach Park. Perfect for couples or anyone seeking a peaceful stay at their very own private resort. It’s the ideal space to unwind and rejuvenate away from all the hustle and bustle.

The outdoor pool area features a spacious deck with sun loungers and an umbrella for shade. A vibrant pink flamingo float is set in the sparkling blue water, surrounded by a fenced grassy yard and a few trees in the background.

5 out of 5 average rating, 21 reviews

Pool Paradise with Game Room & Canalfront

Welcome to your Port Charlotte getaway! This charming 3-bedroom, 2-bath canal-front home invites you to unwind in comfort and style. Enjoy the sparkling pool, game room with stunning water views, and outdoor dining area perfect for warm Florida evenings. Whether you’re here for a short escape or a long retreat, our fully-equipped kitchen and spacious living area offer everything you need for a relaxing stay. Come make memories in a place that feels like home!

Guest suite in Punta Gorda

A hammock is suspended between two palm trees in a verdant backyard, providing a relaxing spot. In the background, a two-story tiki hut and a dock are visible along the calm canal, complementing the serene outdoor environment.

4.82 out of 5 average rating, 83 reviews

2 room suite private bathroom & entry.

Enjoy your own 2 room suite in this lovely secluded neighborhood. The bamboo floors and light colored wood make your space bright and cheerful. The back yard features a 2 story tiki hut, hammock, fire pit, and dock for your relaxation. Arrive by land or by sea. The sailboat access canal is only 300 yards from the Peace River and the dock is powered 110V. The home is at the end of a cul-de-sac with a large open area in front of the house.

Popular amenities for Charlotte Harbor rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.88 out of 5 average rating, 26 reviews

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

A serene outdoor pool area is enclosed by a screened lanai, featuring a clear blue pool reflecting the surroundings. A comfortable chair sits beside the pool, complemented by a shaded umbrella. Lush greenery and colorful plants create a calming backdrop.

4.97 out of 5 average rating, 112 reviews

PORT CHARLOTTE FLORIDA RETREAT, 2/2, PRIVATE POOL

The spacious pool area is enclosed by a protective screen, with the shimmering water reflecting a vibrant sunset. Palm trees frame the scene, while the canal with moored boats is visible in the background, enhancing the tranquil waterfront atmosphere.

5 out of 5 average rating, 47 reviews

Harbors edge Retreat- no fee for heated pool

A fenced-in outdoor area features a heated pool surrounded by a screened enclosure. Two blue lounge chairs are positioned nearby, and the sun reflects off the clear water. Lush greenery is visible beyond the enclosure, providing a serene backdrop.

4.86 out of 5 average rating, 64 reviews

Heated pool, family and pet friendly, sleeps 10

An outdoor covered lanai is shown, featuring a wooden dining table surrounded by several chairs. A comfortable seating area includes a woven couch with decorative pillows. A gas barbecue grill and a pool area with water views are visible in the background.

4.8 out of 5 average rating, 122 reviews

Waterfront Home Heated Pool, Lift, Pedal Prowler

5 out of 5 average rating, 8 reviews

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

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.

5 out of 5 average rating, 32 reviews

Hidden Gem in Punta Gorda

5 out of 5 average rating, 3 reviews

Home in Englewood

Gulf Front Escape + Beach Access, Pet Friendly

Condo rentals with a pool

4.96 out of 5 average rating, 126 reviews

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.

Condo in Englewood

Sunset Beach

4.95 out of 5 average rating, 64 reviews

Condo in Punta Gorda

One bedroom condo - overlooking harbor!

4.92 out of 5 average rating, 26 reviews

Two condominium buildings are visible from the marina, featuring colorful exteriors and multiple floors. A calm waterway reflects the structures, with several boats docked along the wooden pilings. Lush greenery and palm trees surround the area, adding to the coastal ambiance.

Condo in Punta Gorda

Burnt Store Marina- Harbor Towers, 2bdrm, GulfView

4.79 out of 5 average rating, 141 reviews

Condo in Englewood

Entire Beachside Condo! Don’t worry Beach Happy!

4.96 out of 5 average rating, 101 reviews

An aerial view reveals a mid-century vacation villa surrounded by lush greenery and open spaces, with the coastline and sandy beach visible in the distance. The calm ocean water stretches towards the horizon beneath a partly cloudy sky.

Condo in Venice

Vintage Villa, Thirty-Five

4.97 out of 5 average rating, 105 reviews

Condo in Englewood

Studio, pool, private beach, boat dock shark teeth

5 out of 5 average rating, 14 reviews

A year-round heated pool is surrounded by sun loungers, offering a spacious area for relaxation. Palm trees line the background, and the view extends toward the water under a clear blue sky with scattered clouds.

Condo in Port Charlotte

Private Beach, Fishing Dock & Heated Pool Paradise

4.95 out of 5 average rating, 65 reviews

An aerial view captures the vibrant yellow condominium building, surrounded by lush palm trees and well-maintained landscaping. The nearby marina features numerous boats docked in the water, with additional residential buildings and facilities visible in the background.

Condo in Punta Gorda

Burnt Store Marina- 2BR w/ pool, marina, gulf view

Other holiday rentals with a pool

4.98 out of 5 average rating, 41 reviews

A serene outdoor area features a saltwater pool and spa enclosed by a screened lanai. The calm blue water reflects the surrounding greenery and sky. Lush trees are visible in the background, contributing to the tranquil atmosphere.

Home in North Port

New 4-bedroom house with saltwater pool and spa!

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.

4.93 out of 5 average rating, 15 reviews

The Coastal Palm Cottage

4.92 out of 5 average rating, 13 reviews

Cozy 3 Bedrooms/2 Baths w/ heated Pool

A private pool is surrounded by a screened enclosure, featuring clear blue water and a paved deck. Comfortable seating is arranged nearby, with lush greenery visible beyond the enclosure, creating a serene outdoor space.

4.89 out of 5 average rating, 44 reviews

Serenity Haven: 4BR Villa /Heated Pool & Sleeps 8

5 out of 5 average rating, 9 reviews

A contemporary dining area features a round table set for four, surrounded by sleek chairs. Large glass walls provide abundant natural light, revealing views of the outdoor space. A modern chandelier hangs above, adding an elegant touch to the inviting atmosphere.

Home in Rotonda West

Turtle Bay - minutes to Boca Grande!

5 out of 5 average rating, 7 reviews

Pirate's Cove

The open-concept kitchen and dining area feature modern appliances and a spacious island with seating for two. Natural light floods the space through large sliding doors, overlooking the outdoor seating area by the shared pool. A neutral color palette enhances the inviting atmosphere.

5 out of 5 average rating, 47 reviews

Stylish Waterfront Gem with Scenic Views and Charm

A private screened-in pool area is visible, featuring a clear blue pool surrounded by a spacious concrete deck. The pool is bordered by a protective mesh enclosure, with lush greenery seen in the background, enhancing the serene outdoor space.