Holiday rentals with a pool in Cypress Lake

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, 115 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

4.88 out of 5 average rating, 123 reviews

The modern exterior of the home is highlighted by a manicured lawn and tropical landscaping, featuring palm trees and colorful shrubs. A paved driveway leads to a two-car garage, while a covered entrance invites guests into the villa.

Villa in Cape Coral

Heated Pool | Canal | Modern | New | Southern Exp.

Welcome to the brand new, absolutely stunning, Villa Southbreeze! This 3 bedroom, 2 bathroom vacation rental is fully furnished &equipped. Stunning high ceilings, huge 72" fireplace, office, laundry room all Samsung stainless-steel appliances, and much more. Out by the huge screened-in pool area you'll find a private electric heated pool, BBQ propane grill, several loungers, large table + chairs. The heated pool features two fountains and a shallow "beach area". Welcome to the villa Southbreeze!

4.91 out of 5 average rating, 180 reviews

The exterior of the condo complex is shown, featuring a sign that reads 'Casa Bella.' Lush green landscaping surrounds the building, with palm trees and neatly trimmed bushes. Two-story units are visible, highlighting a calm and inviting atmosphere under a clear blue sky.

Condo in Fort Myers

Ft. Myers Quaint Getaway! Minutes from Beach!

My condo is close to the beach, NOT on the beach, nightlife, public transport, and family-friendly activities. It is good for couples, solo adventurers, business travelers, and families (with kids). It's minutes from Ft. Myers and Sanibel Beach. It has a King size bed in the master bedroom and two twin murphy beds in the guest room. Walking distance from a Super Target. Several outlet malls, closest is 2 miles. FYI, not handicap accessible (second floor unit). A few steps to the pool and grill.

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.

4.97 out of 5 average rating, 127 reviews

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.

The backyard features a hot tub in the foreground, with a clear view of a pool in the background. Colorful adirondack chairs are arranged around the pool area, and a spacious house is visible with a screened porch. String lights are seen overhead, enhancing the outdoor ambiance.

4.98 out of 5 average rating, 111 reviews

January Blowout! HotTub+Beach Gear+5 min to Town

-5 min to Downtown Cape/10 min to Yacht Club Beach, 20 min to Causeway Beach, 25 min to Ft Myers & Sanibel Beach -Tropical fenced backyard w/ pool, hot tub, gas firepit, swing chair, hammock & Blackstone grill -Beach essentials, boogie boards, umbrellas, beach wagon, cooler & chairs -Board games, ping-pong, corn-hole, darts, 2 kayaks+life jackets -2 Beach Cruiser bikes + helmets -Relaxing enclosed covered patio + string lights, neon sign & grass wall -Canal access for kayak launch 5 min away

4.99 out of 5 average rating, 102 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

4.83 out of 5 average rating, 115 reviews

The modern kitchen features stainless steel appliances, including a stove and microwave. Adjacent, a stacked washer and dryer are positioned beside a minimalist dining area. Natural light floods the space through a nearby window, highlighting the clean lines and neutral color palette.

Condo in Fort Myers

Cozy Coastal Escape. Close to FMB and Sanibel

Looking for a cozy getaway near the ocean? This charming 2-bedroom rental is just a short drive away from the beach! With bright, airy spaces and a modern, open layout, it’s perfect for small families, couples, or anyone looking for a peaceful retreat. Features: • 2 bedrooms • Fully equipped kitchen • Private patio for outdoor relaxation • Private Pool • Minutes from shops, restaurants, golf courses & beaches☀️ Located very close to Fort Myers Beach & Sanibel Island🏖️

4.9 out of 5 average rating, 119 reviews

Cape Serenity- Luxury Waterfront Residence

This beautiful, fully equipped home is located in the lovely Orchid neighborhood. As the name suggests, serenity will wash over you as you relax and unwind in this gorgeous 3 bed, 3 bath home. Located off of the Caloosahatchee River, this is one of the select few homes in the Cape Coral/Fort Myers area that affords both privacy/luxury and direct accessibility to the gulf. Recent upgrades include a newly refinished pool deck and EV charger to enhance your experience!

4.94 out of 5 average rating, 362 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.

4.96 out of 5 average rating, 284 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.

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.

4.98 out of 5 average rating, 225 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.

4.91 out of 5 average rating, 198 reviews

A screened-in pool area is visible, featuring a clear blue pool with a shallow entry. Sunlight reflects off the water, and a few chairs are arranged around the pool. A shaded outdoor kitchenette is in the background, with a fenced yard beyond.

Apartment in Cape Coral

Private Apartment with sunny pool

One-bedroom plus den apartment attached to the main house with private entrance. The apartment has a small kitchenette for basic meal preparation. A large pool is right outside your door! Come relax by the pool & cool off on a hot day. The pool is for your private use. We have a gas BBQ grill located in the fenced yard for your use. Ft. Myers Beach 35 min away Sanibel Beach 45 min away Naples Beaches 60 min away

Popular amenities for Cypress Lake rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A covered outdoor space features a heated saltwater pool bordered by wide stone tiles. Comfortable lounge seating is seen under an umbrella nearby. Lush greenery and canal views are visible beyond the pool area, offering a serene setting for relaxation.

5 out of 5 average rating, 60 reviews

Coastal Cowgirl - Heated Pool

A private pool is featured within a screened enclosure, allowing for serene views of the surrounding greenery. Sunlight reflects off the clear water, creating a tranquil atmosphere. Outdoor seating is visible nearby, offering a space for relaxation.

4.93 out of 5 average rating, 30 reviews

New Listing Discount 3/2 w/pool

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.

5 out of 5 average rating, 26 reviews

Serene Modern Oasis | Private Pool in Fort Myers

A spacious pool area features a sparkling water surface, complemented by a large umbrella providing shade. Two bright turquoise chairs are positioned in the shallow end, enhancing the inviting atmosphere of the shared heated pool, surrounded by a fenced yard.

5 out of 5 average rating, 69 reviews

5 Star, Heated Pool, Twin Home Located D-town Cape

A modern dining area features a large wooden table set for a meal, complete with plates, glasses, and decorative centerpieces. Stylish pendant lighting illuminates the space, while an adjacent kitchen with stainless steel appliances can be seen in the background.

5 out of 5 average rating, 16 reviews

Blue Skies at Bayshore: Heated Pool, Hut Tub, Dock

A single-story home is featured, displaying a well-maintained lawn and a paved driveway. Lush palm trees and flowering plants are visible, enhancing the inviting exterior. The home has a tiled roof and large windows, allowing for natural light. A garage door is located to the right.

5 out of 5 average rating, 22 reviews

Robin's Nest on a Canal with River and Gulf access

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.

4.94 out of 5 average rating, 187 reviews

Surfside Elegance SW Cape Coral Luxe Vacation home

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, 57 reviews

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

Condo rentals with a pool

The open living area features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table sits in the center, surrounded by a vibrant area rug. The dining area includes a round table with four chairs, and a well-equipped kitchen is visible in the background.

5 out of 5 average rating, 15 reviews

Beachfront @ Elevate in the Sun!

4.98 out of 5 average rating, 42 reviews

An open living area features a dining set with six wooden chairs surrounding a round table. Natural light floods the space, highlighting the textured tile flooring. A staircase leads to a lofted area above, complemented by a wooden railing. A patterned area rug adds warmth to the scene.

Condo in Fort Myers

2 Bed 2 Bath Townhouse with Loft - 6B

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.

4.88 out of 5 average rating, 104 reviews

Beachfront fully equipped apartment

Superhost

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, 203 reviews

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

4.8 out of 5 average rating, 116 reviews

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.

Condo in Bonita Springs

Oceanview unit. Completely remodeled Pool is open!

4.93 out of 5 average rating, 15 reviews

Beachfront, Estero Beach Tennis 708A Weekly Stays

4.97 out of 5 average rating, 98 reviews

A spacious living area is captured, featuring a comfortable couch and a stylish armchair. A large television is mounted on an entertainment unit, while a coffee table with decorative items sits in the center. Soft lighting enhances the open layout, inviting relaxation.

Condo in Cape Coral

Luxury Condo by Cape Harbor and Excellent Dining!

4.9 out of 5 average rating, 101 reviews

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.

Condo in Bonita Springs

Easy Breezy Too

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, 78 reviews

Luxe Riverfront Retreat~Pool~Spa~Bar~Tropical Yard

5 out of 5 average rating, 8 reviews

A two-story condo building features a light-colored exterior with multiple windows and balconies. Lush greenery lines the pathway leading to the entrance doors, while a well-maintained parking area is visible in the foreground beneath a colorful sunset sky.

Townhouse in Fort Myers

Updated Condo w/ Pool and Tennis

A spacious pool area is showcased with a heated pool, surrounded by a screened lanai. Lush tropical landscaping is visible beyond the pool, providing a tranquil backdrop for outdoor living. The expansive area invites relaxation and enjoyment of the surrounding nature.

5 out of 5 average rating, 45 reviews

Backyard Dream-Oasis! - Heated Pool

5 out of 5 average rating, 16 reviews

A comfortable living area is depicted, featuring a light gray sectional sofa and a stylish coffee table. A round mirror and decorative wall art enhance the space. The open kitchen and dining area are subtly visible in the background, creating a welcoming environment.

Townhouse in Fort Myers

Florida Vacation-Fort Myers-Pool-Gated Community

An aerial view of the serene waterfront property showcases a south-facing pool and hot tub, framed by a screened-in lanai. The spacious dock features various seating arrangements, including loungers and a shaded area, all set against the tranquil canal backdrop, enhancing the outdoor experience.

5 out of 5 average rating, 15 reviews

Pool, Hot Tub, Kayaks, Dock & Canal w/ Gulf Access

4.9 out of 5 average rating, 69 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

Tranquil Pool Spa EsCape Villa

4.9 out of 5 average rating, 48 reviews

A comfortable living area features a spacious sectional sofa with decorative cushions. A wall-mounted TV displays vibrant content. Light streams in through sliding glass doors leading to a private balcony, while a neutral-colored wall complements an outdoor-themed artwork.

Apartment in Fort Myers

2BR Vacation Condo Near Ft Myers Beach & Sanibel

A fenced-in screened patio encloses the outdoor pool, showcasing clear blue water under a bright sky. Lush greenery lines the background, enhancing the tranquil outdoor space while the pool ladders offer easy access for enjoyment.