Houses for Rent in Keewaydin, Naples, FL

Property Status: Active Available for annual or off-season rental at $20,000/month, or for the 2026-2027 season at $35,000/month. Situated on approximately 110 feet of waterfront, offering scenic views of one of the widest points of Runaway Bay in Port Royal, this unique 3-bedroom, 3-bath property is truly a great vacation home. Elegantly set back on the exclusive, tree-lined Galleon Drive, the home features hurricane impact windows and doors, a chef's kitchen, spacious living and family rooms, and has been freshly painted and newly furnished with sophisticated, beach-styl

Property Status: Active Step back into a bygone era of classic charm and comfortable elegance. Nestled in the ultra-exclusive, world renowned enclave of Port Royal, Florida, this quiet, very private, oasis invites you to experience old-world charm combined with modern comfort. This splendid waterfront residence boasts 4 graciously appointed bedrooms and 4.5 luxurious bathrooms, sprawling across nearly 4,000 s.f. of living space. This includes a totally separate attached house with a separate entrance. Just steps from the Port Royal Club and Naples famous white, sugar sand

Property Status: Active Beautiful Port Royal neighborhood. Fully furnished with screened barbecue area and plenty of entertaining space. Quiet street and walking distance to the beach and minutes from3rd Street Shops, restaurants and downtown 5th Ave. South. Naples most exclusive neighborhood. Will do a long term lease as well. Enjoy the traditional feel of Naples! Office Phone: (239) 799-5303 Copyright © 2025 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be ind

**3-D VIRTUAL WALK THROUGH AVAILABLE HERE: https my matterport com show ?m=8VGSR4PFoHV Welcome to your perfect coastal escape—just two blocks from the sugar-white sands of Naples beaches! This exquisite 2-bedroom, 2-bathroom residence in the coveted Cambridge Club offers the ultimate blend of luxury, comfort, and convenience in one of Naples’ most desirable neighborhoods. Perched on the second floor, this beautifully furnished home is designed for effortless living. Simply move in, unpack, and begin enjoying the quintessential Naples lifestyle. Imagine mornings spent str

This Unique and Rarely available 2 bedroom, 3 bath Townhouse lives like a home, in the heart of Old Naples. All new kitchen Summer of 24. Only 4 units in the complex sits on the corner of 5th So and 11th Ave So, 5 blocks to the beach or 4 blocks to St. Ann’s school. Freshly painted throughout, two-story screened lanai with balcony, private yard, and one covered parking spot. Listed by: Royal Shell Real Estate, Inc. Listing posted by Linda Castanon (786) 933-9164. [SYNDID 4141990 12042025]

Property Status: Active Escape to this gorgeous villa for a memorable stay! This western exposure 2 Bedroom+Den/2 Bath home is light and bright and has both a modern and comfortable feel. Some extraordinary features of this Honeysuckle floor plan include: ray ceilings, a gourmet kitchen with center island, well-appointed office, spacious great room, spa-like bathrooms, and a large lanai with a picture window screen perfect for relaxing lake and sunset views. The Isles of Collier Preserve is ideally located near downtown Naples and has an abundance of amenities perfectly s

Property Status: Active Currently available for April 2026 at the discounted rate of $12,000 for the month. Newer, pet friendly, single-family pool home, in The Isles of Collier Preserve is available for short or longer term rental. . 4 bedrooms, 3 ½ baths, plus a pool bath. Enjoy this resort-style home with its fabulous outdoor living space. Chill out in the comfortable seating and watch television. Dine outside or relax on lounge chairs out, or in the water! The southern exposure guarantees sun on the pool all day long and the lush preserve view offers privacy. The outdo

Come experience this newly renovated, spacious two bedroom beach-cottage style home for the winter season. The house sits on a large property located in the heart of the popular Bayshore District of Naples. You are within a very short walking distance from a wide variety of popular restaurants, live outdoor music options, as well as boat and jet ski rentals. The house has two spacious bedrooms and bathrooms with walk-in showers. The second floor bedroom also contains a bright, dedicated workspace with open views of the outside, perfect for the "digital nomad". It also boas

Property Status: Active Beautifully Furnished Villa in the Desirable Isle of Collier Community. Welcome to a stunning 2 Bedroom + Den, 2 Bath attached villa offering modern style, effortless living, and exceptional flexibility, available for purchase or lease with an option to buy. This nearly new residence is beautifully furnished and decorated, allowing you to move right in and immediately enjoy the Naples lifestyle. Designed with comfort and convenience in mind, this open-concept villa features a bright and spacious great room, elegant finishes, and a versatile den perf

Property Status: Active Available Season 2026! Bayfront offers a lifestyle of convenience, excitement, and relaxation, perfect for those seeking the best of Naples. Imagine waking each morning to sun-drenched vistas of Naples Bay, with gentle palm trees swaying in the coastal breeze. This spacious two-bedroom, two-bathroom haven boasts 1,518 square feet of light-filled living. Unwind on the expansive balcony, where captivating views of Naples Bay mingle with the enchanting Italian-inspired courtyard. Indulge in endless days of leisure. Dive into one of the two sparkling pr

Property Status: Active Fully renovated 2-bed, 2-bath villa with den at 3 Kings Rd #A7 in Royal Park Villas, Naples. This 1,296 sq ft home features an open floor plan, tile flooring, impact windows, updated appliances, new HVAC and roof. Enjoy a private patio, covered carport, and a beautifully maintained non-gated community. Ideally located just minutes from 5th Avenue South’s shops, dining, and entertainment, and only a short drive to Naples’ white-sand beaches. Nearby schools include Avalon Elementary, Gulfview Middle, and Naples High. Office Phone: (239) 231-3380 Copyr

Property Status: Active Annual rental available! This bright and cheerful 3-bedroom, 2-bathroom furnished Key West style bungalow exudes coastal charm and sits on a quiet, private street near Naples Bay in the highly sought-after Bayshore Arts District. The renovated kitchen features custom cabinetry, quartz countertops, a prep-sink area, decorative backsplash, and stainless steel appliances. Upstairs boasts vaulted ceilings and polished solid teak hardwood floors. Enjoy brand-new bathrooms, including a main-level primary suite with a spa-like shower and freestanding tub.

Property Status: Active Every day is vacation in this waterfront paradise! This recently renovated home is nestled on a quaint cul-de-sac street in the coveted Royal Harbor neighborhood offers effortless Gulf access and a lifestyle of unparalleled luxury. Every day here offers the chance to boat, fish, or simply soak up the sun. From the moment you step inside, the open-concept great room captivates with seamless integration of kitchen, living, and dining areas—perfect for entertaining or relaxed family living. At the heart of the home lies a chef-worthy kitchen ancho

Property Status: Active This top floor, one-bedroom residence has everything that you need in a premier location. High ceilings, neutral tile, and a large balcony create an open and bright setting while stainless steel appliances, an eat-in kitchen, and secured parking provide all of the comforts and conveniences you deserve during your Naples experience. Bayfront offers an array of luxurious amenities on-site including 2 pools, 2 spas, a fitness center, grills, pickleball, tennis, and many outdoor spaces. Bayfront also is home to a selection of delicious restaurants, a un

Property Status: Active Extraordinary newer built and newly furnished, one of the kind modern/contemporary style home. Located only couple minutes away from Naples downtown 5th avenue, as well as, beaches and other key destinations, such as fine dinning, shopping, medical facilities, schools, museums, zoo, parks, botanical gardens and much more! This exceptional property offers 5 bedrooms, 5.5 bathrooms, 2 kitchens, fitness workout space, entertainment area, heated salt water pool + jacuzzi with LED lights, electronically controlled roll down screened patio, fantastic out

Property Status: Active Escape to Naples this season! Available for a 3-month minimum stay. Beginning February 15th 2026. Welcome to your coastal retreat in the highly desirable Arboretum community minutes from downtown Naples, the beaches, and some of the best dining and shopping in Southwest Florida. This first-floor residence offers a stunning long lake view from nearly every window and a bright, open layout perfect for relaxing or entertaining. As soon as you enter you see the water! Enjoy beautiful sunsets from your lanai with desirable western exposure. The home feat

Property Status: Active Beautifully finished turnkey attached Villa in the heart of Olde Naples, offering 2,520 sq ft across three levels with private elevator access. Features a gourmet kitchen, attached garage, and private pool with inviting outdoor space. Available for seasonal rental. Conveniently located near the beach and just a short walk or bike ride to 5th Ave S dining, shopping, and entertainment ideal for enjoying the Naples lifestyle. Office Phone: (239) 287-4044 Copyright © 2025 Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved. All inform

Property Status: Active Lovely 2nd floor unit in Naples Sunrise. This 2 bedroom and 2 bathroom unit is a great getaway for the winter season. With spacious open living and dining area, flat screen TV and view of tranquil landscaped area. The fully equipped kitchen has been updated as well as the bathrooms. Master suite has a queen bed, TV, stand alone closet, and esuite bathroom with shower only. The guest bedroom with queen bed, TV and guest bathroom in same area. There is a quaint table and chairs on the front entrance porch. WIFI, cable, and laundry room are also includ

Property Status: Active Steps from the iconic 5th Avenue Downtown and Naples' beautiful white sandy beaches, this is your opportunity to live within the heart of Olde Naples and reside within one of Southwest Florida's most sought after newer construction luxury downtown condominiums. 875 Sixth Avenue consists of only eight exclusive condominiums within walking distance to all of the great amenities offered within the charming Downtown Olde Naples. Enjoy delicious hors d'oeuvres and cocktails with your friends and family atop your private rooftop before walking to one of t

Property Status: Active Located in the heart of Olde Naples sits this modern yet cozy first floor corner unit in an idyllic boutique building that says Welcome to Paradise. Newly renovated this 1 bedroom 1 bath unit with open floor plan features all stainless Appliances, Gourmet Kitchen, Custom Cabinets & a Large Master Suite is in close proximity to Cambier Park, 5th Ave, Naples City Dock, Dining, Shopping and the Arts. Don't miss the opportunity to live and play in the heart of Old Naples. Office Phone: (239) 799-5300 Copyright © 2025 Naples Area Board of REALTORS. All r

Property Status: Active BRAND NEW HOME.Arboretum, great location , in Naples Bayshore Arts District, 3 miles away from downtown Naples, short distance to Celebration Park, 360 market and next to Botanical Gardens. Close to Gulf Coast's best beaches. This is a brand new home, the Seabright floor plan - second floor coach home offers two bedrooms, 2 baths and a 1 car garage, in home laundry, lanai and a balcony. Perfect open floor plan, dining area adjacent to the kitchen, living area next to the kitchen too and they all look to the screened -in lanai. Huge island where you

Property Status: Active Welcome to this charming retreat in the heart of Naples, FL. This elegant 1,000-square-foot residence offers a perfect balance of comfort and sophistication. Featuring two beautifully designed bedrooms and two immaculate bathrooms, the home provides a serene and inviting atmosphere throughout. The residence comes fully furnished with tasteful décor that complements its coastal charm. Enjoy a thoughtfully updated kitchen with all stainless steel appliances, perfect for everyday living or entertaining. Step outside to a lovely screened-in patio, ideal

Property Status: Active AVAILABLE SHORT OR LONG TERM. Cozy and comfortable Florida home with circular driveway located in the prestigious area of Aqualane Shores! Direct canal front. Bring your boat and tie up to the floating dock. Entertainer's delight from the built-in pool and a hot tub to the many outdoor seating areas. Split bedrooms allow for privacy while the great room provides a fabulous gathering space that flows to the beautiful outdoor living area. Gather on the new deck or sit canal side and enjoy your morning coffee and evening cocktail. Stroll or ride your b