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.

4.96 out of 5 average rating, 135 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

4.97 out of 5 average rating, 134 reviews

Home in Pelican

Cozy in the Cape, Water views & private salt pool

"Unbelievable Views" describe this homes Gulf-access setting. Bring or Rent a boat and dock it right in our backyard. Beautiful Long intersecting canal and majestic palm trees galore! Cozy in the Cape Villa is a TOTALLY REMODELED home with 2 spacious bedrooms and 2 baths. Beautiful Italian Terrazzo flooring throughout, all new appliances & furniture. Epoxy garage floor w/ping pong table. Screened lanai with NEW heated salt POOL(no child protection screen) No Parties ALLOWED. 6 people max allow

4.92 out of 5 average rating, 110 reviews

A spacious screened lanai surrounds a shimmering pool, offering a relaxing environment. Colorful lounge chairs line the poolside, providing ample seating for guests. Lush greenery is visible beyond the screen, enhancing the private retreat ambiance of the outdoor area.

Home in Cypress Lake

Palm Palace - Two House Compound Sleeps up to 22!

This property listing includes full access to two separate on-property houses, both with full access to the pool and giant screened lanai! The main house has 3 bedrooms, 2.5 bathrooms and 8 total beds (1 king, 1 queen, 2 double bunk beds & 2 sofa beds). The smaller "pool house" has an additional full kitchen, living room, 2 additional bathrooms & 3 more beds (2 queen & a sofa bed)! This property frequently is booked by multi-generational families, large groups and even entire sports teams!

4.96 out of 5 average rating, 52 reviews

A living area is featured, displaying a neutral-colored sofa complemented by colorful cushions. A wooden coffee table holds a decorative plant and coastal-themed items. Two patterned chairs provide additional seating, while warm light filters in, adding a welcoming ambiance to the space.

Home in Cypress Lake

Mermaids Cove, don't miss this listing!

Mermaid's Cove is a private tropical retreat ready for guests to relax and refresh! It is a beautifully decorated home with a private pool & bedroom /bathroom on opposite ends of the home. The kitchen is fully equipped open concept. It is located in a friendly, family neighborhood near everything Ft. Myers has to offer. If you enjoy palm trees swaying as you float in the pool or sitting under a patio umbrella while grilling dinner, then this home is for you. Come and renew at Mermaid's Cove!

5 out of 5 average rating, 12 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

4.9 out of 5 average rating, 125 reviews

Home in Cape Coral

Cape Serenity- Luxury Waterfront Residence

This recently renovated, fully equipped home offers serenity and relaxation as you unwind in this gorgeous 3 bed, 3 bath residence. Located off the Caloosahatchee River, it is one of just a few select homes in the area that offers both privacy and luxury, along with direct accessibility to the gulf. Recent upgrades include a newly refinished pool deck, Ev charger, renovated kitchen and bathrooms and modern touches throughout to enhance your experience. Updated photos coming soon!

4.92 out of 5 average rating, 128 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.

4.96 out of 5 average rating, 25 reviews

Home in Cypress Lake

Swimsational Golf views

Recently updated heated pool home backing to a golf course with private back yard. It has a covered patio area with new furniture and outdoor grill. Both bedrooms have televisions and super comfy pillows / linens. The main area has a coffee/tea bar and island in the kitchen. The garage has a brand new washer/dryer with the latest technology. Located in a great residential neighborhood surrounded by shopping and restaurants. 20 minutes to the beaches or downtown Ft. Myers.

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.

4.92 out of 5 average rating, 105 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, 392 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.

Townhouse in Cypress Lake

A spacious living room features a sectional sofa positioned on a large blue rug adorned with turtle patterns. A ceiling fan rotates above, and a mounted TV is visible on the wall. Stairs lead to an upper level with a dining area and additional seating.

4.95 out of 5 average rating, 20 reviews

Townhouse in Fort Myers

Enjoy Fort Myers at its finest while staying in this newly renovated 2 bedroom, 2 bathroom townhome. This quiet gated community offers a pool and spa directly across the parking lot from this unit. LOCATION! LOCATION! LOCATION! Sanibel Island, Fort Myers International airport and downtown Fort Myers all within a 20 minute drive. A variety of activities like putt putt golf, trampoline park, family fun center and lots of shopping only a few minutes away.