Holiday houses in Cypress Lake

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

Private farmhouse stay at Dim Jandy Ranch.

Take it easy at this unique and tranquil getaway. A beautifully appointed bed and bath in a separate building from the house. We have goats, donkeys and chickens and a Highland cow, all super friendly. Sit and relax on your private, beautiful lanai or any of our farm tables placed around the property. Join us as we feed the animals. Or even join in one of our Goat Yoga classes! We're easily located close to I-75, airports, shopping, beaches, downtown. Perfect for couples or solo travelers.

Private & Spacious Studio in Prime Location.

The best location, period. This very quiet and private one bedroom apartment has a paved & shaded parking . To ensure a long night rest there are black out rolls on windows. Private courtyard with Gas grill & side burner. 1 block from Publix supermarket. Walk to FSW State College. Walk to Barbara B Mann theater or Suncoast Arena. 10 miles to Fort Myers Beach. 17 miles to Sanibel Island beaches. 8 miles to Downtown Fort Myers and just 15 miles to the SWF International Airport. 2 parking spaces.

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!

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

Tropical Mango Grove Stay | Whiskey Creek Area

A peaceful Fort Myers hideaway surrounded by lush greenery, palms, and a mango grove in the desirable Whiskey Creek area. Enjoy quiet, secluded privacy in a tropical setting with a spacious, comfortable layout—perfect for relaxing or extended stays. Conveniently located just 15 minutes to Downtown and 20 minutes to Fort Myers Beach, ideal for exploring local dining, nightlife, and coastal adventures, then return to a serene, nature-filled retreat to relax, unwind, and recharge.

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.

SWFL: Lake McGregor Home - Entire Home! 3B/2B

Our home is in a quiet, safe neighborhood perfect for remote work, family getaways, or long-term stays in a kid-friendly environment. Spacious & Fully Equipped: 3 bedrooms • 2 bathrooms • Full kitchen • Washer/dryer • 2-car parking • WiFi • Smart TV • Beach gear available (Cable/streaming not included). Prime Location: 10 miles from Fort Myers Beach, 7 mi from Downtown, and a 7-min walk to Publix, Walmart, and restaurants. RSW Airport is a 20-min drive.

Waterfront with Saltwater Pool, Sauna, Cold Plunge

Experience the epitome of comfort and luxury in our exquisite 4-bedroom, 4-bathroom waterfront wellness retreat. Revel in the tranquillity of water views and be pampered by a host of rejuvenating amenities, including a therapeutic saltwater pool, a soothing sauna, and a refreshing cold plunge. This sanctuary is designed with top-of-the-line features and sumptuous interiors that ensure a restful and revitalizing stay beyond compare.

Sunny Coastal Getaway w/ Heated Pool Near Beaches

Welcome to The Mermaid Lounge! Your sunny coastal getaway with a private heated pool, minutes from beautiful beaches and family-friendly dining. We’ve thought of everything — 3 coolers, 6 beach chairs, wagons, pool floats, toys, games, and baby gear so you can pack light. Enjoy mornings with coffee by the pool and evenings with bubbly while the kids play. Relax, connect, and make lasting memories!

Ocean Blue - Luxurious 4BR home w/heated pool

Skip the "same old, same old" vacation routine and dive into sunshine-infused bliss at our 4-bedroom, 3-bath Fort Myers haven. This isn't your standard close-to-the-beach rental – it's a gateway to epicurean feasts, Outside dining areas, family game nights by the fire, Peloton fitness, and endless days soaking up the Florida Vitamin D (poolside, naturally).

Renovated 4/4 with Fishing, Pool, Boating, Beach

This 4bedroom/4bath private home is located in McGregor neighborhood of South Fort Myers on a quiet and private dead end street. It is on a private mangrove lined canal which connects 5 minutes from open water, and is about 10 minute drive to the beach. This property just had a top to bottom renovation completed in January 2026.