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 Nestled in the heart of Port Royal, Naples' most sought-after neighborhood, this elegantly furnished home offers an unparalleled blend of luxury and comfort. Situated on a quiet street, this residence is just a short walk to the beach and minutes from the fine dining, boutique shopping, and vibrant atmosphere of 3rd Street South and 5th Avenue South. Designed for both relaxation and entertainment, the home features a screened lanai barbecue area, and expansive outdoor living spaces, perfect for hosting guests or enjoying serene Florida evenings. Ava

**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

Property Status: Active The crop of the crop location, the best of the best destination nation wide, home is located at prestigious Port Royals big sister/brother neighborhood Aqualane Shores. This unique classic home is situated on a 0.35 acre homesite right by waterfront of Naples Bay. Neighborhood is surrounded by multimillion dollar estate homes, beautiful mature landscaping, which creates an amazing ambiance and adds a tranquility to this very special with a character property. House has 3 bedrooms, 3 full baths, an office/den and a fairly large size heated swimming p

Property Status: Active Renovated, Waterfront Retreat in the Heart of the Bayshore Arts District. This home has been completely updated with fresh, bright, designer finishes and appliances to create a waterfront sanctuary in a prime location. The elevated living area provides a wonderful and dry perch, with an open concept design, 3 generous bedrooms and 2 full bathrooms. The open living area is anchored by a brand new kitchen, with stainless steel appliances and a large island that serves well for both preparation and entertainment. The primary bedroom features a private

Property Status: Active Welcome to your perfect getaway in the heart of Southwest Florida! This beautifully furnished coach home features a spacious, open floor plan with two bedrooms, a den with a sleeper sofa, and two full bathrooms. The well-appointed kitchen offers an island, crisp white cabinetry, quartz countertops, and stainless steel appliances-perfect for both everyday living and entertaining. Step onto the screened balcony to take in breathtaking SWFL sunsets, or hop on the provided bikes for an easy ride to Celebration Park to enjoy dinner, drinks, and live musi

Property Status: Active Welcome to your dream vacation! This luxury 4-bedroom, den, 3 1/2 bath, pool & spa home is a coastal retreat that combines timeless elegance with modern comforts. It offers a seamless blend of designer finishes and sophisticated charm. Built for both relaxation and convenience, this home is in the award-winning community, The Isles of Collier Preserve, which is located just 4 miles from Downtown Fifth Avenue and 15 minutes to the beach. The community has a full-time Social Director creating daily activities, events and parties. It has a dog park and

Property Status: Active This elegant two-bedroom, two-and-a-half-bath end-unit townhome offers an exceptional waterfront lifestyle just moments from downtown Naples, the white-sand Gulf beaches, and Tin City. Thoughtfully designed, the gourmet kitchen features abundant cabinetry, granite countertops, a breakfast bar, and sophisticated accent lighting, seamlessly connecting to the open living and dining areas. The spacious floor plan is enhanced by timeless marble flooring, plantation shutters, and expansive glass doors that lead to a covered deck overlooking Naples Bay-an

Property Status: Active Super Charming & Move-In Ready! This adorable bungalow has just had a fresh facelift inside & out. Located at the very end of a Quiet, dead-end street in the Bayshore Arts District makes this one a WINNER! A pleasing layout, featuring 3 bedrooms (2 with walk-in closets!) + 2 baths. Primary bedroom has an attached bath with double vanity & NEWLY TILED walk-in shower. Delightfully tropical screened lanal is nice-sized~ great for relaxing & soaking in the solitude of your private backyard oasis. Walk to Avalon Elementary!! Easy access to Naples Botanic

Property Status: Active Welcome to Bliss in Port Royal. This beautiful home offers the finest luxurious accommodations available with soaring ceilings, fabulous light and huge outdoor spaces and gardens. Enjoy the professionally decorated furnishings and decor, brand new gourmet kitchen with 2 Wolf ovens, Wolf gas grill and Sub- Zero appliances, beautiful master bath with dual vanities, soaking tub and steam shower, oversized private outdoor space with huge pool and spa, outdoor bar and gas grill, tropical landscaping and a yoga meditation garden. For the entertainment lov

Property Status: Active Welcome to the Kite House a one of a kind Old Naples family compound only steps to The Gulf of Mexico. This fabulous new Naples Beach Retreat is comprised of three residences sleeping up to 16 people. There are 3 residences comprised of a 3 bedroom, 2 bedroom and one bedroom cottage. The 2 bedroom residence can be rented separately. From the front porches, you are just steps to the sugary sand beaches and a short stroll to the world renowned Fifth Ave and Third Street districts where culture, fine dining and shopping are in abundance. Reserve all th

Welcome to this charming and beautifully maintained 2-bedroom, 1-bath single-family home ideally situated in the heart of Naples. Offering comfort, convenience, and an unbeatable location, this residence is perfect for those seeking the best of Southwest Florida living. Just minutes from I-75, premier shopping, and an array of top-rated restaurants, this home places you close to everything Naples has to offer. Enjoy the ease of daily living with essential amenities nearby—and when it’s time to unwind, the world-renowned white-sand beaches of Naples are only a short drive

Property Status: Active Plan Your Beach Vacation Now! Welcome to the "Kite House," a charming Old Naples retreat just steps from the Gulf of Mexico. This listing features the beautifully designed 2-bedroom, 2-bath residence, perfect for a family getaway or a relaxing couples' retreat. Enjoy all the comforts of a newly remodeled property, complete with exquisite decor, thoughtful design, and state-of-the-art appliances., Relax on the lanai or take a short stroll to the sugary sand beaches. While this listing focuses on the 2-bedroom, 2-bath residence, the "Kite House" is pa

Property Status: Active Brand-new lakefront villa available for annual rental in the award-winning Isles of Collier Preserve. This unfurnished, pet-friendly rental combines with resort-style amenities to deliver an unparalleled lifestyle in one of Naples' most sought-after communities. Step into the sunlit great room, where soaring tray ceilings and a fully tiled open-concept design set an elegant tone. Expansive sliding glass doors lead to a screened lanai overlooking the lake-perfect for enjoying morning coffee or winding down with an evening cocktail. Outside, your priv

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 su

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 1/2 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 out

Come experience this newly updated, 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 boasts

Property Status: Pending 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 Copy

Property Status: Active Rental available - 3 month miniumum! 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 freest

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 anchored b

Property Status: Active This is a remarkable Olde Naples gem located one block from the beach on the iconic palm tree-laden street of Broad Avenue South. This four-bedroom home includes a private courtyard with your very own pool, spa, grill, and outdoor dining space. This is a private oasis, complete with a dedicated workspace, three-car garage, pine wood floors, Viking appliances, and a spacious owner's suite complete with his and hers ensuite bathrooms. Find yourself enjoying Naples in the heart of the Historic District. This elevated Olde Naples cottage is perfectly si

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 outd

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 © 2026 Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved. All inform