Holiday rentals with a pool in Estero

4.93 out of 5 average rating, 119 reviews

Flat in San Carlos Park

Resort Style Pool Adj Beds-Wilder Sunset Views!

Perfectly located 2 Bedroom 2 Bath condo! Nestled on a public golf course with a wonderful pool area, it is the perfect combination for a peaceful vacation. The condo is centrally located by everything one needs to relax and enjoy the Fort Myers area. We have gone the distance to make your vacation memorable. The spacious condo has adjustable beds, which will provide you sweet dreams. Close to the beaches, shopping, airport, golf, and tons of restaurants. Guests can also enjoy the pool area.

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, 155 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 bright kitchen area is featured, showcasing a white table with a marble top and a bowl of oranges. Behind, large glass doors provide views of the outdoor screened pool area, which is furnished with a dining table and stylish seating.

4.97 out of 5 average rating, 214 reviews

Central 3BD/2BA •Massive Heated Pool •Golf courses

🌞 Gorgeous Heated Pool Home Near Everything – Perfect for a Relaxing & Convenient Getaway! Welcome to your tropical escape in the heart of SW Florida! This beautifully maintained 3BD/2BA home is located just minutes from world-class beaches, and top local attractions, offering the perfect blend of tranquility, comfort, and accessibility. Whether you're here for a family vacation, a romantic getaway, or a business trip, this home provides everything you need for a restful and memorable stay.

4.99 out of 5 average rating, 108 reviews

Comfy 3 BR-Group Friendly-Pool Access-BBQ-FGCU

Everything your group needs to be comfortable. 2 car garage w/remote Plenty of FREE on-site driveway parking for large work vehicles Logo vehicles ok Screened lanai w/ seating & BBQ Washer/Dryer Free, secure WiFi Smart TV in all rooms & 65” TV in Living Room Electric fireplace Well-stocked kitchen Keurig & Drip coffeemaker Toaster/crockpot Soap (laundry, dish, body, hair) Bathroom Items (Hair dryer, flat iron) Pantry items Community Pool Access 1 mile-Low fee Pack & Play & baby bath support

A vibrant living area displays an orange accent wall adorned with a colorful bird artwork. A comfortable sofa with assorted cushions is positioned alongside a stylish coffee table, topped with a decorative arrangement of colorful items. A green armchair and lamps provide additional seating and lighting.

4.95 out of 5 average rating, 186 reviews

Colorful condo with heated pool and private WiFi

We welcome you to stay in this amazing vacation home with all the amenities and comforts of home in Southwest Florida. Enjoy relaxing in this wonderful two bedroom (one king, one queen), two full bathroom unit with a private patio and a spacious kitchen. Spend your days relaxing by the pool or playing tennis and shuffleboard. Check out some local attractions of Ft Myers Beach, Naples, and Sanibel Island all within just a short drive of the home. This will truly be a home away from home!

A bright kitchen area features a wooden countertop with a stainless steel sink and dishwasher. The space opens to a screened-in patio showcasing a heated pool and outdoor dining area, enhancing the seamless connection between indoor and outdoor living.

4.94 out of 5 average rating, 103 reviews

Classic Arcades Heated Pool Home by Beach & Dining

Escape to a relaxing beach vacation in this beautiful optional heated pool home with epic arcade game room. Includes king size beds in all bedrooms and 6 smart TVs. Features 2 family rooms and 2 fully equipped kitchens (indoor & outdoor). Offers private backyard with full outdoor kitchen, smart TV & BBQ Grill. Fully stocked home with kitchen supplies, beach essentials, bicycles, high speed internet and more. Perfect for families, couples & professionals looking for a Florida Beach Escape!

A screened patio overlooks a serene swimming pool surrounded by lush greenery. Two lounge chairs are positioned nearby, with a small table featuring colorful drinks. A few inflatable toys float in the water, offering a casual ambiance for relaxation.

4.97 out of 5 average rating, 116 reviews

3BR w/HUGE 2k sq ft Lanai & Seasonally Heated Pool

Welcome to your peaceful Bonita Springs retreat, perfectly located near Naples, Ft. Myers, shopping & beaches! This isn’t just a rental, it’s our 2nd home and we treat it as such. You'll experience "exceptional" the minute you enter this stunning, open concept interior. Further, it boasts a striking 2000 sq ft screened-in lanai w a seasonally heated pool. This outdoor oasis doubles your living space and offers a flying pest barrier and significant UV protection. Breathe/Smile/Unwind

4.92 out of 5 average rating, 120 reviews

A resort-style pool area is showcased with a stone patio, featuring several lounge chairs and two shaded umbrellas. Palm trees stand nearby, and a rock formation is visible within the pool's edge, complementing the serene outdoor setting.

Home in Iona

Experience of a lifetime

Get ready for the experience of a lifetime at this hidden gem! As you walk through the front door you will begin your journey into the best vacation of a lifetime. Keep on going through the sliders & that will lead you to the incredible resort style pool that will leave you in awe!!! Here you are in the heart of it all. Shopping-dining-entertainment is all within a 5 minute drive. The beautiful beaches just 7 miles away. If you enjoy boating & relaxing this is the place for you.

A solar-heated swimming pool features clear turquoise water within a screened enclosure. Lush greenery and trees are visible in the background, complemented by soft lighting from the setting sun. A white pool edge and a handrail provide access to the water.

4.87 out of 5 average rating, 174 reviews

Beautiful Oasis

Relax at the solar heated pool and enjoy the serenity of the beautiful, and peaceful 0.6 acres of land with a natural pond where different types of birds like egrets, herons, and ducks can be seen. Close to shopping, dining and just 7.5 mi to Bonita Beach Park. If you play Golf, The Bonita Fairways Public Golf Club is 2.8 mi. Or buy a day pass at the Hyatt Regency and spend the day at the lazy river and waterslides. The backyard is all fenced in, ideal to let your dog run.

4.94 out of 5 average rating, 377 reviews

Home in McGregor

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 spacious living area is presented with two gray sofas and two blue armchairs arranged around a decorative coffee table. A large television is mounted on the wall, and natural light filters through the plantation shutters, illuminating the room's light-colored tile flooring.

5 out of 5 average rating, 133 reviews

Bonita Retreat: Heated Pool - Minutes to Beach

We know that you’ll love it here – whether you spend your time lounging by our pool, or at beautiful Barefoot Beach, less than 3 miles away. Our home is close to everything, so many beautiful beaches, great shopping and world class restaurants. If dining-in is more your thing, you will have a fully stocked kitchen with every amenity you could wish for. This is our own vacation home, so we’ve made every effort to make it as comfortable and convenient as possible.

4.97 out of 5 average rating, 299 reviews

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.

Home in Cape Coral

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.

Popular amenities for Estero rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 57 reviews

A spacious screened pool area is shown, featuring a heated saltwater pool with built-in bench seating. Lounge chairs are positioned along the edge, and a hammock is visible nearby. The outdoor dining area and sectional seating are included, with a 55" Smart TV situated to provide entertainment.

Home in Bonita Shores

Private Palm Oasis - Close to Beach

5 out of 5 average rating, 4 reviews

Bright Bonita Springs Pool Home Near Gulf Beaches

A tranquil pool area features clear turquoise water, surrounded by tropical landscaping. Sunlight reflects on the water's surface, highlighting a stone seating area and lush greenery. An outdoor dining space with shaded seating is visible nearby, creating a serene atmosphere for relaxation.

5 out of 5 average rating, 26 reviews

Gulf Access, Resort Pool home, with Tiki bar.

A single-story home is set against a clear blue sky, featuring a well-kept lawn and garden. Subtle landscaping surrounds the entrance, and a two-car garage is visible. The front door is framed by large windows, inviting natural light into the living space.

4.93 out of 5 average rating, 27 reviews

Duquesne of southwest Florida.

An open concept living area is showcased, featuring a spacious seating arrangement with a light-colored sofa and chairs. A dining space with white wooden chairs surrounds a circular table. Natural light filters through large windows, illuminating the carefully curated decor and tiled flooring.

4.93 out of 5 average rating, 57 reviews

Beautiful private getaway in Bonita Springs

An open-concept living space is highlighted, featuring a large white sectional sofa and a natural wood dining table. Light-colored cabinetry and modern appliances are visible in the kitchen area, while warm tones of the flooring and decor create a welcoming atmosphere. Ceiling fans and natural light enhance the ambiance.

5 out of 5 average rating, 38 reviews

Luxury Modern Coastal Home w/ Pool & Game Room

A modern home is set against a colorful sunset. The facade is characterized by a symmetrical layout with a covered entryway and large garage. Lush landscaping features palm trees and well-maintained grass, offering a welcoming exterior to guests.

5 out of 5 average rating, 14 reviews

Lovely home nestled near Sanibel & Ft. Myers Beach

5 out of 5 average rating, 92 reviews

Remodeled 4 BR 3 Full Bath Sunshine Getaway

Apartment rentals with a pool

Apartment in Bonita Beach

A spacious living area features comfortable black leather sofas and a light-colored armchair arranged around a glass coffee table. Large sliding glass doors provide access to the balcony, allowing natural light to fill the room. A textured area rug sits beneath the seating arrangement.

4.91 out of 5 average rating, 130 reviews

Bonita Beach and Tennis 1903

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.

4.89 out of 5 average rating, 114 reviews

Beachfront fully equipped apartment

4.83 out of 5 average rating, 120 reviews

Gulf Water Views + 2 bikes, beach gear weekly stay

A sparkling pool features a waterfall and is surrounded by palm trees. Lounge chairs are positioned around the pool area. In the background, views of the bay are visible under a clear blue sky, creating a serene vacation atmosphere.

4.92 out of 5 average rating, 210 reviews

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

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

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 Shores

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.

4.94 out of 5 average rating, 142 reviews

Amazing Condo-1 mile from Bonita Beach

Apartment in North Naples

A bright living area features a comfortable seating arrangement with a neutral sofa and a reclining chair. A coffee table is positioned centrally, with a scenic view of the ocean visible through expansive sliding glass doors, leading to a balcony with outdoor seating.

4.97 out of 5 average rating, 152 reviews

Bonita Beach and Tennis 3907 - Ocean Views

Other holiday rentals with a pool

5 out of 5 average rating, 4 reviews

True Florida Charm! Bonita Springs Heated Pool

A bright living area is decorated with a spacious brown sofa and two light grey chairs. A modern television is mounted on the wall above a dark console. Large glass doors offer views of the outdoor space, framed by light curtains. Fresh greenery is visible in the corner.

5 out of 5 average rating, 77 reviews

Modern Coastal Retreat / heated pool and hot tub

A spacious living area featuring a comfortable sectional sofa and a contemporary television stand. A desk and chair are positioned near a window, providing ample natural light. The kitchen area showcases wooden cabinets and modern appliances against a backdrop of tile flooring.

4.9 out of 5 average rating, 20 reviews

Private 2BR Suite w/ Separate Entrance

A spacious screened-in pool area is showcased with a turquoise swimming pool and surrounding seating. Outdoor furniture includes a dining table and lounge chairs, complemented by vibrant tropical plants. Sunlight filters through the mesh enclosure, enhancing the inviting atmosphere within the outdoor space.

4.91 out of 5 average rating, 11 reviews

Casa Piña Bonita, The Ultimate in Coastal Living!

A screened-in patio area features a large dining table surrounded by six chairs, facing a private pool. Natural light filters through the mesh enclosure, highlighting the inviting blue water of the pool and the greenery visible through the transparent walls.

4.9 out of 5 average rating, 41 reviews

Seashell Sanctuary

5 out of 5 average rating, 29 reviews

A spacious outdoor area features a heated swimming pool surrounded by a screen enclosure, enhancing airflow while providing comfort. A lounge area with colorful seating is present. The interior showcases a modern kitchen and a cozy living space with ample seating, all well-lit by natural light.

Home in Willoughby Acres

Huge 5BR • Heated Pool, BBQ, 3 Suites • Nr Beaches

4.67 out of 5 average rating, 6 reviews

Home in Bonita Shores

Beautiful 3 bed home-heated Pool, close to Beach

A comfortable living area features a relaxed seating arrangement, including a black futon and a beige chair. Natural light filters through a sliding glass door, leading to an outdoor space. A decorative rug sits under a circular wooden table, complemented by light-colored walls.