Holiday rentals with a pool in Fort Myers

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

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

TikiTime Tropical Riverfront Retreat

This riverfront home offers the perfect blend of comfort, luxury, and Florida charm. Nestled in a quiet neighborhood, your friends and family will enjoy breathtaking water views from sunrise to sunset. Step outside to your own resort-style oasis featuring a sparkling pool, relaxing hot tub, and entertaining at the tiki bar—ideal for unwinding with a cocktail in hand. With ample outdoor seating, you’ll have plenty of space to dine, soak up the sun, or simply watch boats drift by on the river.

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.

Heated Pool + Hot Tub |3BR | Large Pool|Sleeps 10

•Prime Location: Just minutes from Sanibel & Captiva Islands • 10-minute walk to movie theaters, shops, and restaurants • 8 min to Fort Myers • 10 min to Cape Coral Water Park • 25 min to the airport • Perfect for families & remote work • 5 Smart TVs • Fast Wi-Fi • Family-friendly amenities & games • Fully equipped kitchen • Washer & dryer • Sofa bed • Beach towels & bathrobes • Outdoor living: • BBQ grill • Outdoor dining area • FREE onsite parking • Easy self check-in

Escape to the "Oasis"!

DISCOUNTS: Weeks...1=10%, 2=15%, 3=20%, 4=25%. Welcome to the "Oasis"! Escape to the water and stay on a canal in beautiful Cape Coral! Enjoy this 3 bedroom, 2 bath home. Swim in the pool, sit on the patio, fish from the dock, sit at the tiki bar for a drink, or take a nap on the lanai to get away from it all! There is a 50 foot long dock with 30 and 50 amps, so bring your boat! The Gulf is accessible by boat and Ft Myers Beach & Sanibel/Captive Island activities and beaches nearby!!

The Pearl | River Views | King | Pool+HotTub+Gym

Welcome to The Pearl — a bright 17th-floor retreat in the heart of Downtown Fort Myers, with river views from every window. Sleep four comfortably with a king bed and a full sofa bed. Cook in a complete kitchen, work by the window, and do laundry in-unit. Downstairs: resort-style pool, hot tub, gym, game room, and movie theater — all included. The River District's restaurants and bars are a short walk away. Self check-in, fast WiFi, and everything you need for one night or one month.

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.

River Views / Luxury 2BR/2BA, Pool, Walk downtown

Wake up to breathtaking Caloosahatchee River views through floor-to-ceiling windows in this luxurious 2-bedroom, 2-bath apartment in the heart of Downtown Fort Myers. Walk to restaurants, bars, and entertainment, then unwind by the resort-style pool or enjoy the fitness center, movie theater, and free parking. Whether you're visiting for business, a family getaway, or a relaxing vacation, you'll find everything you need for a comfortable and memorable stay.

Luxury Riverfront Estate & Pool

Your Property This spacious waterfront home features a bright open floor plan with expansive water views throughout the main living areas. Guests can enjoy a fully equipped chef’s kitchen, large dining area, comfortable living room, private pool, dock, outdoor entertainment spaces, and a dedicated game room. The home was thoughtfully designed to maximize the waterfront setting, with large windows showcasing beautiful bay views from sunrise to sunset.

Luxury Riverfront:Pool, Tiki Bar & Outdoor Kitchen

Reconnect and relax at this spacious riverfront retreat, perfect for gathering with family and friends. This custom coastal home offers 4 bedrooms, 4 bathrooms, and 3 separate living areas, giving everyone room to spread out and unwind. Enjoy morning coffee while watching boats, dolphins, and manatees pass by, then spend the day soaking in the heated saltwater pool and spa. Guests may enjoy the views, but the dock is not available for boat use.

Still available for Jan, Feb, March 2027

This well-maintained 4-bedroom, 3-bathroom home is thoughtfully furnished to meet all your needs. The location is a standout feature—just off US-41 and only minutes away from top restaurants, shopping malls, parks, and more. Don’t miss the inviting outdoor area, complete with a private pool and a fully fenced backyard—perfect for relaxing or entertaining. 🌴