Vacation rentals with a pool in Cypress Lake

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Top-rated rentals with a pool in Cypress Lake

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

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Superhost

Home in Fort Myers

4.83 out of 5 average rating, 167 reviews

Blue Beach Bungalow

3 large bedrooms (2 queens, one king) plus a full den, laundry room, HEATED pool and the house has its own beach with an in-ground fire pit that seats 12, lounge chairs, and sunset views! Walking distance to shopping centers, great restaurants, 20 minutes to RSW Airport and Fort Myers' white-sand beaches, perfect for a romantic get-away and 10 minutes from downtown Fort Myers Completely remodeled in July of 2021 with brand new appliances electronics, and all the creature comforts you can imagine

Top guest favorite

The exterior of the home features a well-maintained façade with a combination of light brown stucco and stone accents. Lush greenery surrounds the entrance, including palm trees and flowering plants, complemented by a circular driveway and a clear blue sky overhead.

Home in Fort Myers

5 out of 5 average rating, 20 reviews

Casa Del Sol

Escape to paradise at Casa Del Sol. This updated home is located 14 miles from the airport in a quiet, upscale neighborhood, and is centrally located. Enjoy your days with a short drive to Sanibel, Fort Myers Beach or Lovers Key State Park. Shopping, restaurants, theaters, golf, and boating are all nearby and very abundant! Jet Blue Park and Hammond Stadium are under 10 miles. Enjoy your time relaxing at the house on the especially private lanai, with a heated plunge pool, BBQ and seating.

Top guest favorite

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 Caloosahatchee

4.97 out of 5 average rating, 119 reviews

Boater’s Paradise-Stunning Sunsets! Games Room!

Newly renovated! 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 the stunning sunsets on the water!

Guest favorite

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.

Home in Fort Myers

4.97 out of 5 average rating, 179 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.

Top guest favorite

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

4.98 out of 5 average rating, 121 reviews

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.

Superhost

A light-filled living room features a comfortable sectional sofa and a coffee table in a soft blue hue. A flat-screen TV is mounted on the wall above a dark wooden console. Large glass sliding doors provide views of the lake and bring in natural light.

Home in Fort Myers

5 out of 5 average rating, 3 reviews

Fabulous Condo With Pools! 33% Monthly Discount!

Discount on 30 day condo rental overlooks a small lake and is a 20 minute drive to one of the best beaches in Florida, Fort Myers Beach! Also, this lovely place is close to all shopping, restaurants, hospitals, and bike trails. Just a 15 minute drive to the quaint Downtown Fort Myers! Splash and swim in the two pools, hot tubs or work out in the air conditioned fitness room. You may even have the golf cart to cruise to the amenities or the Bone Fish just outside of the gate.

Top guest favorite

The living room features a spacious sectional sofa, providing ample seating. Large glass doors open to the outdoor area, enhancing natural light. A mounted TV displays beach scenery, while a modern fireplace adds a touch of warmth. The room's design promotes comfort and relaxation for guests.

Home in Pelican

4.97 out of 5 average rating, 110 reviews

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

Unwind Cape Coral welcomes you to sunny southwest Florida, close to magnificent beaches, fishing, shelling, Minnesota Twins Spring Training & much more. Come enjoy this new construction home with heated pool, Kayaks, heated and cooled game room (PlayStation 5), gulf access - salt water canal, 4k oled tv's & many more refreshing amenities. You will love this clean & bright home with lovely décor. Located in the highly sought after Pelican neighborhood of Southwest Cape Coral!

Top guest favorite

A screened-in patio area reveals a clean pool surrounded by lounging chairs. The pool features a gentle curve and easy access steps. Lush greenery and palm trees provide a serene backdrop, while the adjacent living space is faintly visible through large windows.

Home in Fort Myers

4.94 out of 5 average rating, 342 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.

Top guest favorite

A dining area is presented with a large wooden table surrounded by upholstered chairs. A centerpiece of greenery and fruit adorns the table. The walls are painted in a soft blue, complemented by decorative seahorse artwork and a stylish light fixture.

Home in Fort Myers

4.98 out of 5 average rating, 219 reviews

“Dream Vacation”Pool.Near airport&baseball

A few short miles from RSW International Airport, beaches, Twins/ Miracle's baseball, and downtown Ft. Meyers (McGregor). Walking distance to FSW Sunpark stadium. Safe and quiet neighborhood. Private pool *NOT HEATED*. Lanai TV has streaming service so you can log into your account. Click on our picture to view our five homes in Cape Coral/Ft. Myers/Delray Beach. All beautiful & with exceptional Super-host service and care.

Top guest favorite

A sparkling pool is nestled within a lush tropical landscape, surrounded by vibrant greenery and palm trees. Colorful floats rest on the water's surface, while a hammock invites relaxation nearby, creating a tranquil outdoor retreat.

Home in Fort Myers

4.9 out of 5 average rating, 146 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.

Guest favorite

A spacious bedroom features a wooden bed with a light-colored blanket and accent pillows. Natural light streams through two windows and French doors, highlighting the wood flooring and area rug beneath the bed. A decorative lamp and a nightstand add to the room's charm.

Home in Pelican

4.94 out of 5 average rating, 183 reviews

Surfside Elegance SW Cape Coral Luxe Vacation home

This elegant spacious 3 Bedroom + Den, 3 Bathroom house with split floor plan and large living room will truly make you feel home! High ceilings, a lot of natural light, large rooms, amazing Florida canal view, large heated pool. Fully remodeled in 2017 and feels like new. Location is amazing, close to Marina, Cape Harbour, restaurants. Excellent, beautiful and safe neighborhood. This home is perfect for your vacation!

Guest favorite

An inviting pool area is surrounded by a screened enclosure, allowing natural light to illuminate the sparkling water. Comfortable lounge chairs are positioned alongside, while a dining space with a table and chairs is visible in the background, enhancing the outdoor experience.

Home in Fort Myers

5 out of 5 average rating, 14 reviews

Serene Modern Oasis | Private Pool in Fort Myers

Welcome to your private oasis! This stylish, fully equipped home is perfect for families, couples, or friends. Enjoy a private pool, outdoor dining, fire pit, and game room — all set in a peaceful neighborhood near beaches, dining, and fun. With a modern kitchen, comfy living spaces, and tropical vibes, it’s made for relaxing and making memories. Your perfect getaway starts here!