Naples, FL Vacation Rentals With Pools Filters Filters Bedrooms 2 + 3 + 4 + 5 + Bathrooms 2 + 3 + 4 + Clear Filters Amenities Air Conditioning Arcade Machine Babysitter On - Request Baking Sheet Bathtub BBQ Grill - Gas BBQ Grill - Private BBQ Grill Area BBQ Grill Utensils Beach Essentials Bed Linens Bedroom - Step Free Access Bedroom - Wide Doorway Bicycle Bird Watching Blender Boating Body Soap Car - Necessary Car - Recommended Carbon Monoxide Detector Ceiling Fan Chef - Fee Chef - On Request Childrens Dinnerware Cleaning During Stay - Available Cleaning During Stay - Fee Cleaning During Stay - On Request Cleaning Products Clothes Drying Rack Coffee Coffee Maker Common Space - Wide Doorway Common Surfaces Disinfected Concierge - Available Conditioner Cooking Basics Deadbolt Lock Desk Chair Dining Area or Room Dining table Dishes & Silverware Dishwasher Disinfectant Used While Cleaning Downtown Dry Cleaning - On Request Eco Tourism Electric Vehicle Charger Essentials Extra Pillows & Blankets Fenced Yard Fire Extinguisher First Aid Kit Fishing - Bay Fishing - Deep Sea Fishing - Pier Fishing - Surf Flat Smooth Pathway to Front Door Freezer Gambling Game Room Groceries - Fee Groceries - On Request Guest Gap Period - 24 Hours Guest Gap Period - 48 Hours Gym/Fitness Room - Community Hair Dryer Hammock Hangers Heating High Chair Horseback Riding Hospital Hot Tub Hot Tub - Private Hot Water Hot Water Kettle Ice Maker Iron & Ironing Board Jet Skiing Kitchen Kitchen Island Laptop Friendly Workspace Laundry - Fee Linens High Temp Wash (140 degrees) Living Room Long Term Stays Allowed Luggage Dropoff Allowed Marina Microwave On the Golf Course Outdoor Dining Outdoor Seating & Furniture Outlet Covers Outlet Shopping Oven Pack & Play Travel Crib Paddle Boating Parasailing Parking - Free Parking - Private Path to Entrance Lit at Night Patio or Balcony Pets - Not Allowed Playground or Play Area Playroom Pool - Community Pool - Heated Pool - Private Refrigerator Sailing Satellite or Cable Self Check-In & Check-Out Shampoo Shopping Shower Gel Single Level Home Smart TV Smoke Detector Snorkeling Sound System Stove Sun Loungers Swimming Tennis Court - Community Toaster Towels Toys TV View - Golf Course View - Lake Washer - Private Water Sports - Available Waterfront Wifi Wifi - Free Wildlife Viewing Wind Surfing Wine Glasses Zoo Pet Friendly Type Apartment Condo House Apply Filters Where SkyRun Naples United States Florida Greater Naples Area Ave Maria East Bonita Springs East Naples Fort Myers Beach Golden Gate City Naples Park & Vanderbilt Beach North Naples 34120 Twin Eagles Old Naples Park Shore & The Moorings - People 2+ Guests 3+ Guests 4+ Guests 5+ Guests 6+ Guests 7+ Guests 8+ Guests 9+ Guests 10+ Guests 0 Pets 1 Pets 2 Pets Search 1-6 of 6 results Show122436 Sort byBedrooms - Low to HighBedrooms - High to LowName - a to zName - z to aDefault (random) Favorites MAP Featured Property Naples StoneCreek Modern Great Schools Resort Amenities Naples, FL 5 Bdrms 4 Baths 10 Guests From $1,591/night incl. feesnext avail Jun 10–11, 2027 View Details New PropertyFeatured Property Naples Seychelles Amazing Decor by Sky Run Monthly Naples, Florida 3 Bdrms 2 Baths 6 Guests From $231/night incl. feesnext avail Sep 29 – Oct 26 · 27-night min View Details New PropertyFeatured PropertyFlexible Cancellation Fort Myers Beach Estero across from ocean Fort Myers Beach, FL 4 Bdrms 3 Baths 10 Guests From $727/night incl. feesnext avail Sep 29 – Oct 2 · 3-night min View Details New PropertyFeatured Property Naples Twin Eagles Monthly starting Feb 15 2027 Naples, FL 4 Bdrms 4 Baths 8 Guests From $1,139/night incl. feesnext avail Feb 15 – Mar 14, 2027 · 27-night min View Details New PropertyFeatured Property Naples Twin Eagles Kinross Home Golf pool spa pickleball Naples, FL 3 Bdrms 2 Baths 6 Guests From $638/night incl. feesnext avail May 31 – Jun 27, 2027 · 27-night min View Details New PropertyFeatured Property 5th Ave. Old Naples Monthly Beach Naples, FL 2 Bdrms 2 Baths 4 Guests From $339/night incl. feesnext avail Jan 2–29, 2027 · 27-night min View Details Search while moving Prev1LastNext Naples, Florida Vacation Rentals With Heated, Private, and Shared Pools Make the most of the Florida sunshine with a Naples vacation rental featuring a pool. Whether you are looking for a home with a private pool, a heated pool, or access to a community pool, having a place to cool off and relax can make your Naples getaway even better. SkyRun Vacation Rentals offers properties with pools throughout the Naples area, including options near Vanderbilt Beach, Naples Park, North Naples, East Naples, and Old Naples. Depending on the property, additional amenities may include WiFi, a hot tub or jacuzzi, lakeview outdoor spaces, and pet-friendly accommodations. There is plenty to enjoy away from the pool, too. Spend the morning along the Gulf of Mexico, visit Naples Pier, explore the shops and restaurants at Mercato, or discover waterfront neighborhoods such as Royal Harbor. Naples also makes a convenient home base for day trips to Bonita Springs, Marco Island, and Estero. After a day at the beach, on the water, or exploring Southwest Florida, return to your rental for an afternoon by the pool. Browse SkyRun’s Naples vacation rentals with pools to find the right property for your stay. Check each listing for details on pool type, heating, availability, and other included amenities.
