Vacation rentals with a pool in Estero

4.97 out of 5 average rating, 132 reviews

A clear blue pool is surrounded by a spacious patio, featuring comfortable loungers partially immersed in the water. The inviting outdoor space overlooks the serene canal, while the covered lanai offers additional seating options. Lush palm trees sway gently in the background under a bright sky.

Home in Cape Coral

Boater’s Paradise-Stunning Sunsets! Games Room!

Renovated lanai! This 3 bed/4 bath home is on the nicest canal with 200+ ft of frontage & gorgeous views of the canal & sunset. The pool, tiki hut & docks have full sun all day. Each bedroom has a private bath & there's a 2 pc powder room off the laundry. The primary has a king bed & walkout to pool. The 2nd bedroom has a queen bed & pool access. Bedroom 3 has a queen & private bath. Fully equipped kitchen with everything you need. And a games room! Enjoy stunning sunsets under the tiki hut.

Superhost

The guesthouse exterior features a modern design with a metal roof and a two-car garage. Landscaped front yard with green grass and decorative plants is visible, creating a welcoming entrance. A secluded porch area with seating is present, surrounded by trees and shrubs.

Guesthouse in Fort Myers

4.88 out of 5 average rating, 112 reviews

Hezekiah's 2 Story Guesthouse with Pool

Hezekiahs Guesthouse a perfect getaway in sunny SWFL! You will be staying in the guest house with a private entrance. This property has a living room and kitchenette downstairs and a spacious bedroom with master bathroom upstairs. This Airbnb is attached to our home. You will have access to the pool and our outside grill area. Complimentary coffee, water, soda and more.. Lots of nearby restaurants and shopping. Minutes away to Fort myers or Bonita beach, FGCU and RSW Airport and Hertz Arena.

4.95 out of 5 average rating, 241 reviews

An open living area is viewed from a dining space, featuring a large wooden table set for meals. Comfortable seating is arranged around a coffee table, with large windows providing an unobstructed view of the pool area outside. A television is positioned on a black media console.

Home in Naples Park

3 bdrm up to 6 guest pool walk to Vanderbilt Beach

Our home is located in the heart of North Naples. It is less than 1mi. to the beautiful white sand Vanderbilt Beach. Our brand new remolded non-smoking, 3 bedroom 2 bath home is surrounded by numerous local restaurants, entertainment and shopping centers. It's less than 1mi to the newest Naples hot spot "The Mercato". It's 10 min to downtown Naples, 15mi to Miromar Outlets SWFL top place to shop. You can relax in our open floor plan that leads out to the deck of private Pool and hot tub.

4.93 out of 5 average rating, 119 reviews

A clean outdoor pool is surrounded by a safety fence, with clear blue water reflecting the sky. Several lounge chairs are positioned nearby for relaxation, while lush greenery and an open landscape are visible in the background, creating a serene atmosphere.

Apartment in Fort Myers

Golf & Pool Views! Pet Friendly/Super Hosts

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, 154 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, 209 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, 107 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 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, 115 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

4.94 out of 5 average rating, 372 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 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, 128 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.

A scenic view showcases Bonita Beach, where the soft sand meets the calm blue waters of the Gulf. Lush palm trees line the beach, with a dining area set back from the shore. A vibrant building is visible, providing options for beachside refreshments.

4.9 out of 5 average rating, 105 reviews

Easy Breezy Too

Steps from the beach! Easy Breezy 2 is cute, cozy and clean.Unit is stocked with plenty of amenities and extras. Coffee provided for every morning of your stay! Daily vouchers are included for beach chairs set up for you ( VIP service) @ Bonita Jet Ski& Parasail across the street behind Doc’s House. ( a $22 per day value. Umbrella is NOT included) AND as a VIP guest you will also receive a 10% discount on parasailing! Come see how easy breezy it all is!

A cozy sleeping area features a queen size bed dressed in a nautical-themed quilt. A small refrigerator and microwave are visible, along with a dresser and television. Light enters through a shuttered window, complementing the soft blue walls.

4.83 out of 5 average rating, 234 reviews

Cozy studio 1.3 miles to Barefoot Beach

Very inexpensive way to get close to the beach and still have complete privacy! Whole unit-Share nothing. Small and cozy studio/room 12x19 with a refrigerator, microwave, air conditioner, full bath, suitable to more or less sleep. Queen size bed. Closet and dresser. This is a separate guest room with a private entrance not connected to another unit. Located in an adorable tropical feel complex in a seafoam green building.

Popular amenities for Estero rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A screened-in pool area features comfortable seating arranged around a fire table. The heated pool is visible in the background, framed by lush greenery outside the screened enclosure. A grill is located nearby, enhancing the outdoor space for relaxation and entertainment.

4.92 out of 5 average rating, 63 reviews

Welcome Ft Myers 3br/2ba pool vacation- dogs ok

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.

4.95 out of 5 average rating, 20 reviews

Duquesne of southwest Florida.

The screened-in pool area features a sparkling swimming pool surrounded by a spacious deck. Natural light filters through the mesh enclosure, reflecting off the water. Outdoor seating is provided by a small table and chairs, with trees framing the serene backdrop.

4.96 out of 5 average rating, 135 reviews

Waterfront Pool Home. Minutes to Sanibel & Beaches

A serene pool area features a champagne-style hot tub connected to a shimmering pool, surrounded by a marble deck. A vibrant mural of a sea turtle decorates the wall, while lounge chairs are positioned nearby, inviting relaxation amidst lush tropical landscaping.

4.98 out of 5 average rating, 152 reviews

Luxe Unique: Close to Beach, Hot Tub, Heated Pool

A serene backyard space features a winding pool surrounded by lush greenery and colorful lounge chairs. A gazebo offers shaded seating, while pool floats in vibrant colors rest on the water's surface. A patio area provides space for relaxation and outdoor dining.

4.98 out of 5 average rating, 51 reviews

Studio Backyard Oasis | Pool, Hot Tub, Fire Pit

5 out of 5 average rating, 91 reviews

Remodeled 4 BR 3 Full Bath Sunshine Getaway

A large heated pool is showcased within a spacious screened lanai. Comfortable lounge chairs are positioned beside the water, and a serene backyard is visible beyond the pool area, featuring lush greenery and flowering plants.

4.96 out of 5 average rating, 149 reviews

Renovated Pool Home in Historic Bonita Springs

5 out of 5 average rating, 15 reviews

Simply Secluded with beautiful pond view

Condo rentals with a pool

Condo in Fort Myers Beach

A contemporary living space features a comfortable sofa and a coffee table adorned with decorative items. Large glass doors open to a private balcony with ocean views, allowing natural light to fill the room. Soft colors and minimalistic decor create an inviting ambiance.

4.98 out of 5 average rating, 50 reviews

Beach Sanctuary Condo

A light-colored sofa is positioned in the living area, accompanied by two textured poufs on a circular rug. In the background, a plush bed with a wooden headboard is visible, flanked by lamps. Coastal-themed artwork decorates the wall above the bed.

4.98 out of 5 average rating, 48 reviews

Sally’s Seaside Escape – Walk to Beach + Views

A panoramic view of the Gulf of Mexico is captured from the fifth floor. The ocean's varying shades of blue meet the sandy beach, lined with palm trees. A beach house is visible near the shoreline, enhancing the coastal atmosphere.

4.95 out of 5 average rating, 40 reviews

Oceanview Oasis on Bonita Beach Bld3 Floor5

4.98 out of 5 average rating, 56 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.

Condo in Fort Myers

Cathy Condo

A row of modern condos is situated along a sandy beach, with palm trees lining the shore and the Gulf of Mexico visible in the foreground. The sky is partly cloudy, offering a serene coastal view.

4.81 out of 5 average rating, 121 reviews

Oceanview unit. Completely remodeled pool is open!

4.94 out of 5 average rating, 104 reviews

A cozy living area features a spacious light-colored sofa and two armchairs, complemented by a glass-topped coffee table. A ceiling fan provides airflow, while natural light pours in through large glass doors. A television is mounted on the wall, enhancing the room's functionality.

Condo in Park Shore

Lush tropical 1st floor getaway in Naples

4.92 out of 5 average rating, 132 reviews

A modern living area is highlighted by a white sectional sofa and a circular glass dining table surrounded by stylish white chairs. Large windows provide views of a tranquil outdoor space with greenery and water, complementing the bright interior decor.

Condo in Naples

Beautiful Pool 5m to the Beach Downtown & Shopping

4.93 out of 5 average rating, 15 reviews

A spacious studio condo features a cozy living area with a plush sofa and decorative pillows. The open kitchen area is equipped with modern appliances and a dining table. Natural light fills the room, highlighting the clean lines and neutral tones of the decor.

Condo in Bonita Beach

Bonita Beach and Tennis 2808

Other vacation rentals with a pool

4.91 out of 5 average rating, 76 reviews

An outdoor lounge area features comfortable turquoise seating arranged around a small table. A palm tree provides shade, while a pink horizon reflects on the water. The sparkling infinity pool is accompanied by a pink floating device, creating a relaxing atmosphere.

Villa in Cape Coral

Heated Pool & Spa Family Villa

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.

4.88 out of 5 average rating, 17 reviews

Private 2BR Suite w/ Separate Entrance

The spacious living area features a modern design with a sleek grey couch and a decorative abstract wall piece. A cozy fireplace is positioned beneath a large television. Natural light floods the room through large windows, enhancing the inviting atmosphere.

4.89 out of 5 average rating, 28 reviews

Renaissance Oasis Retreat

Apartment in Bonita Springs

The living area features a blue couch facing a mounted television. A round dining table with two chairs is set near the window. Natural light highlights the outdoor screened pool area visible through the glass doors, complemented by tropical decor on the walls.

4.97 out of 5 average rating, 92 reviews

Heated Pool•7min to Beach•Pets Welcome

4.95 out of 5 average rating, 19 reviews

Apartment in Cape Coral

Blue Fish Apt 4- Downtown Blue Resort-Heated Pool

4.95 out of 5 average rating, 19 reviews

An open living area features a kitchen island with seating for four, surrounded by white cabinetry and stainless steel appliances. A comfortable seating area with light gray furniture invites relaxation, complemented by natural light streaming through multiple windows. Decorative accents add a welcoming touch.

Home in Fort Myers Beach

Paradise Found

4.98 out of 5 average rating, 55 reviews

A private backyard features a heated saltwater pool surrounded by a spacious patio. Two loungers are positioned beside the water, while a dining table with an umbrella is visible in the distance. Tropical landscaping and trees provide a serene backdrop.

Home in Naples

Newly Renovated Home Just Minutes From The Beach!

An open-concept living space features a modern kitchen island with a marble countertop, accompanied by sleek white cabinetry. A large flat-screen TV is mounted on the wall, and plants add a touch of greenery. Natural light floods through expansive windows, enhancing the airy atmosphere.