Vacation Rentals By Owner In Naples, FL

Enjoy gulf-access waterfront living in the hip Bayshore Arts district of downtown Naples at Dockside Shore! This beautiful home is surrounded by lush mangroves and breathtaking western sunset views. The interior boasts a large eat in kitchen with water views. Wake up to water views in the primary bedroom. The abundance of outdoor living space is ideally setup for enjoying time outside on the water. Arrive by boat and hop right into your heated pool and hot tub. The lanai has an outdoor mini fridge, sink, seating, and outdoor dining. The location is walking distance to restaurants, bars and coffee shops including popular local attraction Celebration Park which is a food truck park with outdoor bar that often has live music right on the water. Just down the road is the famous Naples Botanical Garden and local beaches in Olde Naples are within 3 miles of the house. Naples Bay and the Gulf of Mexico are accessible via the waterway behind the house should you want to bring a boat or rent one while in town. Enjoy laid back Florida living right in the heart of downtown Naples at Dockside Shore!brbrThe Holiday Life is a full service luxury vacation and seasonal rental management company with an expansive portfolio - from beachfront, to downtown and amenity rich communities throughout Naples and Marco Island. Our team is here to assist in every step of planning your experience from choosing the perfect rental, pre arrival planning, dedicated concierge services and 24/7 support during your stay. We look forward to the opportunity to host you! brbrRENTAL PURPOSE: This property is intended for single-family and transient guest rentals only - any requests for work crews require specific approval prior to booking. No commercial vehicles or work trucks may be parked on site. brbrCOMMERCIAL USE: Commercial and/or business use of the property is not allowed, including commercial photography or filming. brbrMINIMUM AGE REQUIREMENT: Primary guest whose name is associated with this booking must be at least 25 years of age and must be present for the duration of the reservation. brbrGUEST LIST: A guest list including full names and ages of all people who will be staying overnight must be provided in writing at least 24 hours to the guest(s) arrival.

Dockside Shore- Waterfront Home in Bayshore Arts District of Naples

Naples, Florida, United States

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Bath

Sleeps

Exceptional(6)

$128.7

Soak up the sun and the gorgeous Gulf of Mexico views at our 2 bed / 2 bath corner unit located on the 8th floor in building 2 of Vanderbilt Surf Colony! The sprawling views from the oversized corner balcony include the Vanderbilt Channel, Bay, Delnor-Wiggins State Park and the Gulf of Mexico. Check-in is a breeze with our convenient keyless entry, which allows direct access to the home upon arrival! All home info is sent to you before your vacation begins to ensure you have important info at the ready. brbrA separate balcony in the master suite offers some more private relaxation, overlooking the community pool & the Gulf. The ensuite master bathroom features an oversized walk-in shower & walk-in closet, as well as a vanity with seating. Fully equipped kitchen with everything you need and more for hosting, including breakfast bar and dining for 6. brbr***Note for Peak Season: The first season rental needs to start on or before January 1***brbrWIFI included. Cable & streaming in the living and master bedroom. Beach chairs & umbrella available. One assigned (covered) parking spot and additional guest parking available. brbrMaster - KingbrGuest Bedroom - QueenbrbrVanderbilt Surf Colony is located in North Naples at Baker-Carroll Point on Vanderbilt Beach. This location off Bluebill Avenue is at the very northern end of Vanderbilt Beach adjacent to the Delnor-Wiggins Pass State Park. This location is within walking distance of LaPlaya Beach and Golf Resort. Close to the Ritz-Carlton, Mercato, Waterside and Artis-Naples. Amenities at the Vanderbilt Surf Colony include a pool, tennis courts, fitness room, community room, barbecue grilles and extra storage with pool/beach supplies available.brbrProperty Code VSC801brbrYou can rent the 2023 Ford Bronco with a 10% discount for your booking at VSC801.br/us/en/suv-rental/united-states/fort-myers-fl/ford/bronco/3091684brbrPlease see below for additional booking requirements:br* 30 day minimum stay. Note for Season: The first season rental needs to start on or before January 1. February - March Bookings: Single and two month bookings are only allowed if the previous month of the property you are reserving has been rented. ***Note for season 2025 the February rental needs to start on January 31.*** Pickup trucks are not allowed per HOA. br* Many communities require submission of an HOA application and associated fees. These applications are typically due 30 days prior to check-in. These fees are NOT included within the quoted rates when booking.br* These application / transfer fees are not set by Realty Group and are quoted to you in good faith. Prices are subject to change. The current application fees are: $150 application fee.br* Please allow us 24 hours or until the next business day to confirm your reservation. Your reservation is NOT confirmed until corresponding with a member of our team and signing the required rental agreement.br* When making an online reservation, guests will have the opportunity to review/sign our rental agreement to confirm, PRIOR to the down payment being charged. br* 30% deposit due at time of booking. Final Balance due 90 days prior to arrival. Please ask about our cancellation policy, it is more flexible than noted on VRBO.br* For safety, security, and property protection, this home may be equipped with exterior security cameras and/or video doorbells located around the outside of the property. These devices are used only to monitor exterior areas of the home and are not located inside the living space. Cameras may record video and/or audio.brbrThis home may also contain one or more smart home / voice-activated devices (such as Alexa, Echo, Google Home, etc.). These devices are provided for guest convenience and are not intended for guest monitoring or surveillance. Guests may mute, disable, unplug, or turn off these devices at any time during their stay.brbrBy proceeding with your reservation, you acknowledge and accept the presence of these disclosed devices at the property.

8th Floor Oceanview! Large Balcony ~ Steps to Vanderbilt Beach

Naples, Florida, United States

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Bath

Sleeps

Exceptional(19)

$261.61

Located in the The World Tennis Club in Naples. This Condo is just few minutes to shops, restaurants, 4 miles to the beaches & the popular downtown. brbrAmenities fee $150 include: 16 Tennis Courts and Pickle Ball, Bacci Ball Court, 2 Heated Pools & Jacuzzi, Gym, lockers, sauna. Poolside Restaurant, Playground, Basketball Court, & bike-walking paths.brNot a suitable place for events or parties. It's a very strict condo association, more suited to relaxing and enjoying the resort like facilities.

Apartment

Awesome Apartment near the Beach

Naples, Florida, United States

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$1022.59

Kick back 5 star luxury in the heart of Naples! This lakefront pool estate is perfect for entertaining and relaxing. chefs kitchen.brbrWhat to Love:br-Spacious chefs kitchen with modern marble countertops and custom cabinetry.br- 5 Bedrooms + officebr- GREAT FOR ENTERTAININGbr-Saltwater poolbr-Great Natural Lightbr- 2 car garagebr- Fast Wifibr- Fully high end furnishedbrbrbrLong term stay discount available.and relax in this calm, stylish space.brbrThe spacebrEAT: Chefs dream kitchen, fully built in cabinetry with new appliances, Florida hand made with Maple wood cabinet's, Level 7 exquisite Marble countertops, Wine fridge and Bar. ALL TOP OF THE LINE!brfully stocked gourmet kitchen with Microwave, Coffee Maker, Wine Glasses, Pots and Pans, Complete dishes, utensils and serving items.brLiving edge wood table seats 8brBar seats 4brbrSLEEP:br5 Bedrooms (1 King and 4 Queen)brLuxury mattresses (SUPPORT, CERTIPUR US CERTIFIED, High Density Foams with green tea cooling ).brbrSWIM:brOversized saltwater pool overlooking the lake.brbrCLEAN:br3 Full Bathrooms, 3 showers and 1 tub.brbrPlus:brOffice and Bonus spacebrBrand new washer and dryerbr2 car garagebrOther things to notebrPLEASE BE AWARE that Owner utilizes the services of a OUTDOOR security cameras to provide real-time off-site monitoring and security services for the property. By entering into this Agreement, Member/Tenant acknowledges and agrees that Member/Tenant has been given prior notice of the security cameras and noise-monitoring sensors and consents to their usage.brbrSMOKING: This is a non-smoking property and smoking is strictly prohibited inside the home. Any violation will result in User(s) being charged an additional fee of [$500.00],brbrThe Smart Thermostats are hard set to the range of 72-79f. Guests can control to their desired temperature in that range. We must comply to the local power company's recommendations to avoid blackouts and freezings to the AC unit. This is the ideal recommended temperature for our humid costal beach climate.brbrUser accepts all responsibility and will forever hold harmless property owner/manager.

Naples Lake House, Views! 5bd, Privacy

Naples, Florida, United States

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$262.7

Naples getaway, done right. Stay in this stylish 2-bedroom cottage just minutes from beaches, dining, and downtown. Sleeps comfortably with 2 king beds + sofa bed, 2 full baths, and your own private lanai for relaxing mornings and laid-back evenings. Located in a top-tier community packed with amenities—everything you need for the perfect stay.

Cottage

Naples Luxury Cottage-Stylish 2BR in Premier Luxury Community

Naples, Florida, United States

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Select Dates for Price

Very well maintained 2/2 + den 1567 sq ft pool home. This home has a great floor plan with in all new updated stainless steel kitchen appliances and is located the highly desirable North Naples gated community of Ibis Cove, only 2 miles from 1-75, close to great dinning and shopping options and located in an A+ rated school district and only 10 minutes from the beach. Ibis Cove is a friendly and active community with great amenities including a great clubhouse with billiard room, resort- style pool and spa, playground, tennis and Pickleball courts and fitness center Available for immediate occupancy for annual rental

North Naples 2 Bed, den & 2 Bath with PRIVATE POOL for annual rent!

Naples, Florida, United States

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Bath

Sleeps

Exceptional(2)

$211.88

Your home away from home in Naples with 2 marvelous bedrooms featuring 2 queen beds. This superb house also includes 2 bathrooms with a shower and hair dryer. Plus, there's an awesome additional living space with a cozy sofa bed. We hope you enjoy what our place and Naples has to offer.

Costerra Naples 2BED

Naples, Florida, United States

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Bath

Sleeps

Exceptional(1)

$149.53

A mile from beach and walk to Mercato in North Naples in The Pavillion Club Community. 1515 square feet 2 bedroom plus den and 2 bath. Community has a heated pool and clubhouse. 1 covered parking spot comes with the unit. Guest parking available.

2 bedroom plus den and 2 bath

Naples, Florida, United States

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$279.72

This memorable villa is the perfect home base for your trip to Naples. With three comfortable bedrooms, including a king bed, a queen bed, and a sofa bed, guests have plenty of space to relax. The three bathrooms feature both showers and a bathtub, making it easy to refresh after a day of exploring. The villa offers excellent climate control to keep everyone comfortable no matter the season. Step inside this enchanting space and feel right at home. Book now and enjoy everything this fantastic villa has to offer.

Villa

Peaceful 3-bedroom villa I'm Naples FL. Great location

Naples, Florida, United States

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Bath

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$506.9

Beachfront retreat 2 BEDROOM | 2 BATH | Private LanaibrGorgeous ocean views, stunning sunsets & just steps to the sand! brSerene & modern, fully furnished condo with private lanai, new appliances, and a workspace overlooking the ocean. Resort-inspired amenities include a newly-renovated oceanside pool & patio, fitness room, BBQ grills with outdoor dining tables, living room fireplace, and 24/7 front desk security. Perfectly situated within walking distance to upscale shopping and dining. A great place to escape a chilly winter, we hope you enjoy your stay!brbrThere is a $100 HOA application fee required to book this property. This booking is contingent upon signing of lease, HOA approval, & application fee payment per HOA rules. Please allow 25 days for processing.

Modern Beachfront 2-bedroom condo in Beautiful Naples, FL

Naples, Florida, United States

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Bath

Sleeps

Exceptional(8)

$349.98

We know that you’ll love it here – whether you spend your time lounging by our pool, or at Naples’ world-renowned beautiful beaches.brbrThe home is only 10 minutes away from downtown Naples, which features some of the very best restaurants in Florida. If dining-in is more your thing, you will have a fully stocked kitchen with every amenity you could wish for.brbrAs this is our own vacation home, we’ve made every effort to make it as comfortable and convenient as possible.

Naples Retreat: Heated Pool-Minutes to Beach

Naples, Florida, United States

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Sleeps

$296.94

Summary:brbrWelcome to our 616 SunSeeker Cove! This comfortable home offers everything you need for a relaxing getaway, including a private backyard & an open-air, heated pool perfect for soaking up the Florida sun. ☀️ Nestled within our quiet, coastal community & just one mile from the white sands of Vanderbilt Beach - this home is sure to please!brbrbrbrThe Space:brbr Step inside and you’ll be greeted by a light-filled, welcoming interior with a cozy touch of coastal style. This well-kept home is ideal for families or small groups looking for a relaxing vacation or simple beach retreat. The private backyard is a great place to unwind, & the full kitchen includes all the basics to prepare meals at home.brbrbrbr ️ The spacious master bedroom boasts a comfortable king-sized bed, en-suite bathroom & walk in closet.brbrbrbr ️ The queen guest bedroom offers a cozy haven with hotel linens and plenty of blankets to ensure a perfect nights rest.brbrbrbr ️ The third bedroom features two twin beds, perfect for a family or friends' getaway.brbrbrbr Enjoy mornings by the heated pool, afternoons at the beach, and peaceful evenings in the backyard. Whether you're here to explore Naples or just relax in the sun, this home is a great base for your coastal vacation.brbrbrbr☀️ Outside Funbrbr· Southern Facing Backyard w/ Heated, Open-Air Pool Available Year-Roundbrbr· Poolside Lounge Seating w/ Umbrellasbrbr· BBQ Grill Availablebrbr· 4 Beach Cruiser Bikes w/ helmets & locksbrbr· Beach Chairs, Beach Towels, Beach Umbrellas Includedbrbr· Driveway Parking for 3 Vehicles maxbrbrbrbr✅ Interior Amenitiesbrbr· Fully Equipped Kitchen with Keurig Coffee Maker & starter kit of Starbucks k-cupsbrbr· Complimentary Bottles of Waterbrbr· Flat Screen Smart TV's in each bedroombrbr· XFinity High Speed Wi-Fi w/ Boostbrbr· Bathroom with Tub/Shower all towels providedbrbr· Full Size Washer & Dryerbrbr· Starter pack of laundry soap, dishwasher pods & garbage bags providedbrbr· Complimentary shampoo, conditioner, soap & lotion by Barborbrbr· Additional bedding located in room closetsbrbr· Infant items are available upon requestbrbrbrbrGuest Access:brbrGuest have access to the entire home, driveway & private heated pool.brbrbrbrThe Neighborhood:brbrConveniently Located Nearby:brbrbrbrMore informationbrbr- Ritz Carlton Beach Resortbrbr- Turtle Club Beach Resortbrbr- LaPlaya Beach ResortbrbrbrbrWhole Foods, Trader Joe's and Publix grocery storesbrbrbrbrMercato Shopping and Dining District which includes - Whole Foods Market, Sur La Table', Chipolte’, Nordstrom Rack, Blue Martini, Burn Cigar Bar, Cavo Lounge, Bravo Cucina, Seasons 52, Rocco's Tacos, The Pub Naples, AZN, Burntwood Tavern, Silverspot Cinema, The Counter Burger and many more...brbrbrbrWaterside Shops Luxury Shopping & Dining includes – Saks Fifth Avenue, Nordstrom, Anthropologie, Gucci, Apple, Brooks Brothers, Louis Vuitton, J. Crew, Banana Republic, Vineyard Vines and so much more…brbrbrbrThings to dobrbr- LA Fitnessbrbr- Pelican Bay Community Park – Tennis, Sports Fields, Kids Play Areabrbr- Sun-N-Fun Lagoon Waterparkbrbr- Golisano Children’s Museumbrbr- Artis Naples - Home of The Baker Museum & the Naples Philharmonicbrbr- They Naples Players TheatrebrbrbrbrMorning Spotsbrbr-Fit & Fuel Cafe' ***brbr- Starbucksbrbr- Delicious Raw Juice Bar ***brbr- The Patio Cafebrbr- First Watch Breakfast & Lunchbrbr- Dunkin' Donutsbrbr- 239 Coffee ShopbrbrbrbrDining Outbrbr- Capitol Grillbrbr- Tacos & Tequila Mexican Restaurantbrbr- Flemings Steakhousebrbr- The Bay House Restaurant ***brbr- Daruma Japanese Steakhousebrbr- The Crust Pizza***brbr- Inca's Peruvian Kitchenbrbr- Cooper's Hawk Winery & Restaurant ***brbr- Longhorn Steakhousebrbr- Felipes Mexican Taqueirobrbr- Zen Asian BBQbrbrbrbr*** Denotes Favorites :-)brbrbrbrGetting Around:brbrClose to: THE BEACH!! Just a few minutes awaybrbr5 Minutes to Mercato: Dining | Shopping | Theaterbrbr15 Minute drive to Downtown Naplesbrbr45 Minute drive to Marco Islandbrbr45 Minute drive to Sanibel Beachbrbr30 Minute drive to Southwest Florida International AirportbrbrbrbrOther Things to Note:brbrAll standard amenities are offered, to make your stay as relaxed and care-free as possible.brbrIf you need anything extra, or find that something is not functioning properly (or missing), please message us ASAP via the AirBnB messaging app.brbrbrbrInteraction with Guests:brbrThis home is professionally managed by The Beachside Agency. Our homes go through a detailed checklist after each guest departure to ensure the home is in pristine condition for the next guest. Check-in details will be sent two days prior to your arrival. They will include our direct contact number should you have any questions during your stay. A Host will great you within 24 hours of check-in to ensure that you and your guests have comfortably settled in.

616 SunSeeker Cove · Southern Exposure Heated Pool

Naples, Florida, United States

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Bath

Sleeps

Exceptional(15)

$240.87

Feel at Home in this Beautiful Luxury Turn Key 2/2 by the Beach in Downtown Old Naples with Granite & Tile throughout. brbrWalking Distance to The Naples Pier, 5th Avenue & 3rd Street. brbrEnjoy Your Stay! brbrFeatures:brbrCold AC brStunning 4K Ultra HD Smart TvbrBeautiful Sofa and Love SeatbrVery Nice King Bedroom Set with Full Length MirrorbrFine Wood furnishings & Hand Crafted Wall ArtbrDinner Ware / Cook Ware / Iron & Iron Board / French Press / Water Boiler / Coffee Maker / Cutlery / Washer, Dryer & Many Extrasbrbrbr

Walk to the Beach - Downtown Old Naples - Turnkey

Naples, Florida, United States

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Bath

Sleeps

$105.64

Incredible vacation spot only 2 blocks from one of the top rated beaches in Florida. Main ground floor (2 full bedrooms plus open sunroom) condo sleeps 4 very comfortably in an oversized 1350 sqft open concept unit, plus covered front patio space. Cozy, clean and inviting. Updated kitchen and flooring! Pristine gated community with 2 salt water pools, jacuzzi, 6 tennis courts, bocce and beautiful walking grounds. Amazing area with designer shopping at the classy Mercato outdoor mall. Great assortment of restaurants, grocery stores and more. All minutes away!! You will fall in love with the community in this safe, easy to access higher end spot in Florida. Great weather almost year round. Enjoy the tranquil atmosphere of this awesome property, complete with WiFi, heating, AC, and a fitness room. Fall in love with Naples and enjoy the magic it has to offer!!

Naples Florida! Vanderbilt Beach! Perfect Relaxing Sunny Getaway Spot!

Naples, Florida, United States

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Bath

Sleeps

Exceptional(2)

$684.5

Fully equipped first floor 2 bedroom (one w/king bed, one w/twin beds), 2 bath condo with living room with queen sleep sofa, dining area, wet bar, full kitchen, washer/dryer, screened in lanai with view of Naples Bay in the Charter Club Resort, with community swimming pool and jacuzzi and Tiki Bar, complimentary use of grills, fishing poles, beach chairs with umbrellas and bicycles. Available Week 51 Christmas week only.All appliances and furnishings new as of August 2024. Christmas still available for 2025. 15% discount if 6 nights rented on or before October 21, 2025.

1st Fl. 2 bedrm condo w,view of Naples Bay - 5 min from downtown, newly updated

Naples, Florida, United States

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Select Dates for Price

Cottage

LOCATION! New 2-bed 2 bath cottage w soaring ceilings, sunset near town, beaches

Naples, Florida, United States

Your home away from home in Naples with 2 bedrooms. This charming cottage features soaring ceilings built in 2024 it is like new, Brand new appliances, furniture, washer and dryer, and a garage equipped with Bikes to tour the preserve, waterways and catch happy hour at the Isles Restaurant. The lanai faces the sunset, and a large lawn. The bedrooms offer a king and queen bed for a good night's sleep. Isles of Collier Preserve only a few miles from town, beach and restaurants offers the best amenities w 14 pickleball courts, sprawling swimming pools, fitness center, kayaking, tennis, bocce, biking and hiking, a restaurant and events. Guests can stay connected and active during their stay with the resort community. Enjoy your time in Naples at our lovely cottage. This is the best location!! You will not want to leave. They call Isles of Collier - Smiles of Collier -It has it all.

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Bath

Sleeps

$286.75

Now booking for 2025 and 2026! brbrDiscover the epitome of luxury with this exquisite three-bedroom, two-bath condominium nestled in the prestigious Fiddler's Creek community. Elegant granite countertops and dual sinks grace the primary ensuite, while the kitchen invites culinary exploration with its stylish gas range. Each sun-filled room features shutters for the perfect blend of brightness and privacy. Relish the convenience of a tankless water heater for ultimate efficiency, additional guest parking for your visitors, and the welcoming friendly atmosphere amid lush landscaping. Renters have options for privileged access to the impressive 54,000-square-foot club and spa at Fiddler's Creek. This magnificent facility boasts a state-of-the-art fitness center with classes, active pickleball and tennis programs, resort-style pools, and both casual and fine dining experiences. Pamper yourself with the spa's outstanding services or engage in golf and beach activities with optional memberships for never-ending fun and relaxation. Ideally located between the allure of Marco Island and Naples, this condominium offers a lifestyle of both comfort and prestige. Do not miss your chance to rent in Fiddlers! brbrThis unit will be fully furnished, and is available seasonally. Some longer term options available. Please inquire for rates and plans as they vary according to lease lengths / seasons.brbrAdditional fees:br$150 application fee. br$750 Fiddlers Membership Transfer fee (optional)

Meticulously maintained 3BR 2BA resort condo in beautiful Fiddlers Creek Naples!

Naples, Florida, United States

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$854.87

Welcome to an exquisite coastal retreat nestled in the heart of Naples, Florida, where timeless elegance meets modern luxury just moments from the powder-soft sands of the Gulf. This 4-bed, 5-bath, stunning residence captures the essence of upscale Florida living, offering an open-concept design flooded with natural light, soaring ceilings, and refined architectural details throughout. The gourmet chef's kitchen features top-of-the-line appliances, quartz countertops, and a generous island perfect for entertaining, flowing seamlessly into the spacious living and dining areas framed by expansive glass doors that open to a private tropical oasis. A private and quiet office space for any work that needs to be finished. Outside, indulge in the resort-style lanai with a sparkling heated pool and spa, outdoor kitchen, and multiple lounge areas ideal for sunset gatherings or tranquil mornings by the water. The master suite is a serene sanctuary with a spa-inspired bathroom and direct pool access, while additional guest suites provide the utmost comfort and privacy. Perfectly positioned near Naples' most desirable attractions—including Venetian Village, 5th Avenue South, and pristine beaches—this home offers the ultimate blend of luxury, leisure, and location. Whether you're seeking a seasonal escape or an extended stay in paradise, 3200 Crayton Road invites you to experience Naples living at its absolute finest.

Luxury Naples Retreat w/ Pool, Spa & Outdoor Kitchen – Walk to Beach & Venetian Village

Naples, Florida, United States

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Bath

Sleeps

$322.98