Holiday rentals with a pool in McGregor

An outdoor heated pool is enclosed within a screened patio, featuring a spacious deck with lounge chairs. Lush greenery surrounds the area, and sunlight fills the space, creating an inviting atmosphere for relaxation. The pool's clear water reflects the bright blue sky above.

4.95 out of 5 average rating, 129 reviews

McGregor’s Gem• Heated Pool 3BR/2BA River District

🌴 Welcome to McGregor’s Gem—your ideal Southwest Florida retreat! Dive into relaxation in your private heated pool, spread out across three bedrooms and two baths, and enjoy the perfect blend of peaceful tree-lined neighborhood living just minutes from the charming Downtown Fort Myers River District, world-class beaches, and top local attractions.☀️ Whether you’re traveling with family, friends, or on business, this home offers all the modern comforts you need for a relaxing, stress-free stay

4.99 out of 5 average rating, 250 reviews

The screened-in pool area features a serene swimming pool with shimmering water, two blue lounge chairs positioned nearby, and views of a wide canal. A thatched-roof Tiki hut can be seen across the water, surrounded by lush greenery.

Home in Pelican

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

The outdoor area showcases a large pool surrounded by stone patio flooring. Comfortable lounge chairs are positioned beside the pool. Lush greenery and palm trees frame the space, contributing to a private and tranquil setting.

4.94 out of 5 average rating, 157 reviews

Paradise on Estero Bay

Welcome to Mullock Creek a Boater's dream! Southwest views boasting breathtaking sunsets overlooking gulf access canal from your spacious backyard, just minutes away from shopping and dining at Coconut Point, and Gulf Coast Town Center. This stunning Key West Style home has been beautifully maintained and updated offering a lovely front entrance, fully equipped kitchen, spacious Living Room, dining room, Wi-Fi, private driveway with access to the open garage, fully furnished and private pool.

A well-maintained canal property is highlighted by palm trees and a spacious lanai. A 50-foot dock is visible, accommodating watercraft with a boat lift. Colorful Adirondack chairs are placed along the dock, enhancing the outdoor experience beside the tranquil water.

4.99 out of 5 average rating, 181 reviews

Escape to the "Oasis"!

DISCOUNTS: Weeks...1=10%, 2=15%, 3=20%, 4=25%. Welcome to the "Oasis"! Escape to the water and stay on a canal in beautiful Cape Coral! Enjoy this 3 bedroom, 2 bath home. Swim in the pool, sit on the patio, fish from the dock, sit at the tiki bar for a drink, or take a nap on the lanai to get away from it all! There is a 50 foot long dock with 30 and 50 amps, so bring your boat! The Gulf is accessible by boat and Ft Myers Beach & Sanibel/Captive Island activities and beaches nearby!!

4.97 out of 5 average rating, 149 reviews

A serene outdoor space features a rectangular swimming pool surrounded by a spacious patio with patterned pavers. A red umbrella provides shade over one of the lounge chairs, while lush greenery borders the area, enhancing the inviting feel of the backyard.

Cottage in Fort Myers

20 min to the beach! Pool, fire pit, 3bd/2.5ba

*Zero damage in all of the hurricanes* Welcome to Double Palm Cottage located at 899 Dean Way, Fort Myers, FL. The 3-bedroom cottage with 2.5 baths and pool is situated in the Historial District directly off picturesque Royal Palm Tree lined McGregor Boulevard leading directly to the Edison and Ford Winter Estates. The cottage just 20 minutes to all the local beaches, shopping, and fine restaurants. Additional entertainment activities include Major League Baseball spring training games.

5 out of 5 average rating, 9 reviews

4BR Waterfront Home w/ Heated Pool & Private Dock

Waterfront Coastal Retreat | Heated Private Pool + Dock | Dining + Beaches Unplug, unwind, and settle into effortless coastal living at this beautifully renovated 4-BR waterfront home in Fort Myers’ quiet, upscale Town & River neighborhood. You’ll enjoy a peaceful setting while staying close to everything—so many local restaurants are just minutes away, and the area’s best beaches are an easy drive: Sanibel Island beaches are about 15 minutes (9.6 mi) & Fort Myers Beach is about 18 mins

The modern ranch-style home is framed by lush greenery and manicured lawns. A light blue front door invites entry, while palm trees provide a tropical feel. The driveway leads to a garage, and sunlight filters through scattered clouds, illuminating the landscape.

4.95 out of 5 average rating, 146 reviews

Yacht Club Villa | Gulf Access & Heated Pool

Experience the ultimate Florida lifestyle in our stunning, modern ranch-style villa, perfectly situated in the prestigious Yacht Club Area. Completely remodeled with a "split floor plan," this 3-bedroom, 2-bathroom home offers the perfect balance of privacy and togetherness. Whether you're a boating enthusiast or a sun-seeker, this home is designed for you. The heart of the house is the spacious, open-concept living area featuring a new gourmet kitchen and a large dining space.

A serene outdoor area features a private pool with a unique shape and a spa nearby. Sun loungers are positioned beside the pool, surrounded by lush tropical landscaping. A covered patio area is visible in the background, offering a shaded space for relaxation.

4.93 out of 5 average rating, 101 reviews

Serene Pool & Spa Home near Beaches & Downtown

Where prime location meets tropical paradise. Welcome to your very own private poolside and spa oasis, minutes from the beach! Close to Sanibel Island, Fort Myers Beach & Bunche Beach, as well as local shopping, amazing restaurants, fun nightlife in Downtown Fort Myers and the winter homes of Thomas Edison & Henry Ford. Fully renovated throughout. This remarkable space can accommodate up to 10 guests, making it the perfect destination for a family or friends vacation!

4.95 out of 5 average rating, 387 reviews

Whole cozy house

Entire cozy house just for you friends and family. Perfect to spend a pleasant and relaxed moment. If you plan to have a party or event, this place is NOT for you. The neighbors are very strict in terms of noise and large groups of people. Well maintained house. CLEAN POOL BUT NOT HEATED. Walk in to a living area and separated dining. 20 minutes to airport, 25 minutes to the beach, fine dining and entertainment. For a virtual tour, click on the cover photo twice.

A screened-in lanai features a tranquil heated pool with a spa, surrounded by paver stones. The sunset reflects on the water, providing a picturesque backdrop. Palms sway gently in the breeze, enhancing the serene setting suitable for relaxation and enjoyment.

4.97 out of 5 average rating, 308 reviews

Dolphin beach house 2

ONE OF THE BEST WATERFRONTS IN CAPE CORAL! A short walk to the beach a. This 2,500+sq ft home has stunning sunsets and South Western water views from all main living areas,as well as the Master Suite. Heated pool w/ LED colored lighting, built in Spa,Pool bath, full laundry facility, Lanai,Fireplace ,Wi-fi and TVs in every bedroom, private dock . Boat on lift for rent w/RPM rentals . Large 2-car garage w/5 bicycles,beach wagon & cooler on site.

4.94 out of 5 average rating, 103 reviews

A screened-in pool area presents a tranquil space for relaxation. The clear water of the pool reflects the surrounding sunlight, while comfortable seating arrangements are showcased. Lush greenery is visible in the backdrop, enhancing the serene atmosphere of the outdoor space.

Villa in Cape Coral

It's Paradise: Casa Canal Raleigh

Casa Canal Raleigh: A tranquil oasis for discerning vacationers and families who relish comfort in a premium tropical-style environment. Whether you’re an adult seeking relaxation or a family yearning for quality time, this charming retreat offers the perfect blend of serenity and style. Welcome to your own slice of paradise! Casa Canal Raleigh (Haus auf Raleigh Kanal, Maison sur Raleigh Canal, Dom na Raleigh Canal, Главная на Raleigh канал🌴

4.91 out of 5 average rating, 181 reviews

Dive into Luxury: Stunning Tropical Home & Pool

Escape to a tropical paradise in this stunning 1952 midcentury modern home, perfectly located in the heart of historical McGregor Boulevard - home to the famous palm trees planted by Thomas Edison. Indulge in delicious meals at local restaurants like McGregor Cafe and McGregor Pizza, or tee off at the nearby public golf course. And if you're looking to hit the beach or explore downtown, both are just a short drive away.

Popular amenities for McGregor rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 54 reviews

A clear blue pool is framed by a screened patio, providing a spacious area for relaxation. White lounge chairs are positioned beside the water, and palm trees are visible in the background, enhancing the tropical feel. A boat dock is seen in the distance.

Home in Pelican

Close to Cape Harbour western pool and dock, golf

5 out of 5 average rating, 5 reviews

19th Place Paradise

4.97 out of 5 average rating, 78 reviews

Luxury King Bed Home w/ Pool, Hot Tub & Fire Pit

4.95 out of 5 average rating, 20 reviews

A serene backyard showcases a sparkling pool surrounded by light-colored pavers. Five lounge chairs with colorful striped towels are positioned poolside, inviting relaxation. Lush greenery and a wooden fence frame the area, creating a private and tranquil outdoor space.

Home in Cypress Lake

NEW Coastal, Eclectic, Pool & Bikes, Sleeps 9

Aerial view of the Coastal Rose Bungalow surrounded by greenery and residential homes. The lush backyard is visible, along with the heated private pool. Nearby, the expansive waterway glistens under a clear blue sky, showcasing the scenic surroundings and coastal landscape.

5 out of 5 average rating, 64 reviews

Perfect Location! Heated Pool! It’s a vibe!

4.98 out of 5 average rating, 53 reviews

An open living area features a spacious arrangement of light-colored furniture, including a large leather sectional and armchairs. A modern fireplace and flat-screen TV are positioned on a textured feature wall. Natural light floods the space through expansive glass doors that overlook the pool area.

Home in Pelican

Villa Sunset Serenade II

An aerial view captures the serene waterfront home surrounded by lush landscaping. A private pool is set within a spacious backyard, bordered by palm trees. The boat slip is visible along the canal, providing easy access for water activities.

4.91 out of 5 average rating, 47 reviews

Waterfront Retreat with Heated Pool & Boat Slip

5 out of 5 average rating, 4 reviews

Nautical Dream Gulf Access Pool Home

Apartment rentals with a pool

4.75 out of 5 average rating, 108 reviews

A light-filled room features a spacious bed covered with a textured bedspread. Two windows with sheer curtains provide natural light, while a bedside lamp adds a gentle glow. A stylish chair and a small table complete the inviting space.

Apartment in Villas

Sunny Florida condo!

4.9 out of 5 average rating, 260 reviews

A serene view of the Gulf of Mexico features soft waves lapping against a sandy shore, with clear turquoise water meeting an expansive blue sky. The adjacent image shows the condo's exterior with lush green landscaping, highlighting multiple units in a welcoming and well-maintained setting.

Apartment in Sanibel

Rare walkout condo on Sanibel beach

Apartment in Fort Myers Beach

A panoramic view showcases a sparkling heated swimming pool surrounded by lounge chairs, with the beach and Gulf of Mexico visible in the background. Soft waves lap at the shore while sunbathers can be seen enjoying the sandy area. Lush palm trees frame the scene.

4.9 out of 5 average rating, 119 reviews

Beachfront fully equipped apartment

4.97 out of 5 average rating, 63 reviews

A spacious living area is defined by a soft area rug and wooden flooring. Furniture includes a light blue couch, white dining chairs, and a dining table set. Natural light filters through large sliding doors leading to a balcony, with decorative artwork enhancing the walls.

Apartment in Fort Myers

Cathy Condo

Apartment in Fort Myers Beach

A clear blue pool is surrounded by lush palm trees and a rock waterfall, offering a serene atmosphere. Comfortable lounge chairs are positioned nearby, overlooking a tranquil waterway, enhancing the outdoor leisure space.

4.81 out of 5 average rating, 184 reviews

Lovers Key Resort, Fort Myers Beach - Awesome

4.97 out of 5 average rating, 141 reviews

A living area features a black leather sofa, accent chairs, and a flat-screen TV on a light-colored media console. Two framed botanical prints are displayed on a yellow wall, while large sliding glass doors provide sweeping views of the bay and natural light.

Apartment in Punta Rassa

2nd Floor Beachfront Condo Sanibel Harbour

Apartment in Fort Myers Beach

A clear view of a high-rise condominium is shown, with white sand beaches and palm trees in the foreground. The water reflects vibrant turquoise tones under a partly cloudy sky, indicating a pleasant beach environment. Beachgoers can be seen enjoying the shoreline.

4.92 out of 5 average rating, 106 reviews

Lovers Key Beach Club Private Beach

Apartment in Bonita Springs

An aerial view captures a sprawling landscape featuring residential areas interspersed with waterways. The horizon showcases the ocean, with buildings lining both sides of the main road. Lush greenery surrounds the area, providing a sense of tranquility and connectivity to nature.

4.95 out of 5 average rating, 146 reviews

Amazing Condo-1 mile from Bonita Beach

Other holiday rentals with a pool

An inviting screened-in patio features a large heated swimming pool surrounded by lounge chairs. Sculptures adorn the sides of the pool, and lush greenery is visible through the expansive windows, offering tranquil views of the outdoors and tranquil ambiance.

5 out of 5 average rating, 93 reviews

Luxury Riverfront Retreat • Pool & Spa • 60ft Dock

5 out of 5 average rating, 22 reviews

Riverfront Riviera Outdoor TV's/Hotub/Tanning Deck

The spacious backyard features a well-maintained lawn with lounge chairs and a patio area shaded by a large covered terrace. A private boat dock is visible along the canal, lined with palm trees and green foliage, under a partly cloudy sky.

4.89 out of 5 average rating, 28 reviews

Sunnyside - Pool, Hot Tub& Direct access to River

5 out of 5 average rating, 4 reviews

Copa Cabana, House/Cabana, WiFi, close to River

4.99 out of 5 average rating, 70 reviews

A single-story house is presented with a light-colored exterior and a metal roof. Two black garage doors are visible, and a small grassy area is located in front. The peaceful neighborhood setting is complemented by a clear blue sky.

Home in North Fort Myers

3 BR Heated Pool House with Boat Lift

5 out of 5 average rating, 12 reviews

The White House

4.97 out of 5 average rating, 38 reviews

A tropical boaters pet friendly paradise!

A screened-in lanai showcases an inviting heated pool surrounded by stone pavers. A pool ladder leads into the clear water, while colorful lounge chairs and a floating lounge are visible. Palm trees and waterfront views provide a relaxing backdrop to the outdoor space.