Vacation Villa Rentals By Owner In Naples, FL

Available starting May 1 2026. **if you are interested in booking 2027 winter season please note it’s prime time and we book Jan 1-April 30 as one booking. brbrWelcome to Fiddlers Creek, Our gorgeous gated community in Naples. Private Community pool just a few steps away. 3 bedroom, 3 bath, quiet second floor unit with attached 2 car garage. Private workspace with door. The second master has its own terrace and the master and all main living space has huge lanai walkout with sliders. brThe kitchen is newly renovated with all new appliances. New flooring throughout, new furniture, new linens. Feels like a new build, no detail has been missed. Huge lanai with water views and swaying mature palms has 2 eating areas and loungers. There are two large living spaces, two dining areas. Over 2500 square feet all on one floor!brbrGrill included on lanai. High speed Wifi and basic cable is included plus several smart TVs. brNo mail services are available in vacation rental units.brbrEnjoy a quick walk to the club house for a yoga class, a drink at the bar or dinner at the grille ** see optional club membership info below. Montreux community has the best proximity to the club house. Our community also has a private pool a few steps down our road for a quiet, convenient swim. br**The community pool is a quick two min walk and has its own change room and washrooms. Accessible to all renters regardless of club ownership transfer! brbr**All potential tenants will need to pay a one time application fee of $150. The additional clubhouse amenities at Fiddlers are available as an optional transfer to long term renters with a transfer fee payable to the club. If you would like access to the amenities, the community requires a Transfer Fee payable to Fiddlers Club and Spa of $750. If you choose not to transfer the membership you still receive gate access (with optional purchase of fobs), full access to the trails and grounds and complimentary access to the great (and less busy) community pool area on our street. brbrFIDDLER'S CREEK RESORT CLUB AND SPA offers 54,000 square foot of resort living; full service spa, healh fitness center, resort style swimming pools, tennis & pickle ball courts, poolside service, waterfalls, sauna, biking & running trails, poolside bar & grille, pizza nights, live music, fine dining restaurant, and more. The membership services can be reached at (239)732-3000.

Fiddlers Creek Naples Montreux - 3 bd w huge lanai, water views, gated.

Naples, Florida, United States

Bed

Bath

Sleeps

Exceptional(4)

$365.45

Tucked inside the gated Briarwood community of Naples, Florida, bThe Terrazzo Home/b offers the kind of quiet comfort that makes time slow down. Designed with breezy coastal interiors and cared for like a true family home, this bfour-bedroom, 2,500-square-foot villa/b invites you to settle in, stretch out, and feel at home — whether you're here with loved ones, lounging by the pool, or catching sunsets on the shore.brbrInside, you’ll find light-filled, open living spaces thoughtfully arranged for both relaxation and connection. Neutral tones and coastal accents — driftwood finishes, sea-glass colors, soft linens — reflect the easygoing rhythm of the nearby Gulf, without leaning into cliché. A fully equipped kitchen that flows openly, an oversized sectional, and a dining space for eight make everyday living feel seamless and social.brbrWith room for bup to eight guests/b, each of the four bedrooms offers a place to retreat and rest — including a spacious primary suite with a king-sized bed, ensuite bath, and direct access to the pool, two serene queen bedrooms that share a bathroom; and a cheerful twin room ideal for little ones, with its own bathroom. Each room is equipped with its own Smart TV offering a variety of entertainment choices.brbrbFamilies are more than welcome here:/b highchairs, baby crib & gear, board games, books, large flat-screen Smart TVs, movies, and beach essentials are all provided to make your stay feel easy and intuitive. The laundry room is equipped with a washer and dryer, along with everything you need to keep your vacation wardrobe fresh and clean.brStay connected with ease — high-speed internet and unlimited calls within the U.S. are included at no extra cost.brbrStep outside through the sliding doors, and the home truly shines. A screened-in lanai opens to ba private (heated) pool/b framed by tropical landscaping and the gentle hush of the breeze, catching the sun from early morning until late afternoon. Dine al fresco, fire up the grill, unwind with a book in the shade, soak up the sun on a lounge chair, or start your day with a refreshing swim before heading out to explore.brbrGuests can also take advantage of Briarwood’s communal pools, playground, sand volleyball court, basketball courts, and private tennis and pickleball courts.brbrYou’re bjust a 10-minute drive from Naples’ white sand beaches/b — perfect for morning walks along the Gulf or evening sunsets. In town, explore the Naples Botanical Garden, the family-friendly Naples Zoo, and the vibrant charm of 5th Avenue and Old Naples. Or venture further afield with day trips to Marco Island, the Everglades, or the cultural buzz of St. Petersburg — even Miami is within reach on the opposite coast. And when you return, you’ll find not just a rental — but a place ready to welcome you back.brbrThe Terrazzo Home is a well-loved, well-kept space designed for comfort, connection, and the quiet pleasures of Florida living — a place that may feel like home, even if only for a little while.brbr**bAssociation Application Fee (BPOA Fee)/b: A mandatory $100 Association Application Fee is required for each rental (already included in the Booking Fee). An additional fee applies for last-minute bookings: $100 if made within 20 days of arrival, $200 if within 7 days, and $300 for same-day bookingsbrbr**bElectric Vehicle Charging Fee/b: Guests who plan to charge an electric vehicle at the property must notify the host in advance. A charging fee of $10 per day will apply.

The Terrazzo Home – Breezy Coastal Style Pool Retreat in Quiet Briarwood, Naples

Naples, Florida, United States

Bed

Bath

Sleeps

$484.14

A VACATION LIFESTYLE IN ESPLANADE! Situated in north naples Florida, short ride to the shopping, fine dining as well as to the beautiful sugar white sandy beach, FULL GOLF MEMBERSHIP available HOME (4+Den/4.5BA/2 Car) offers a grande great room style floorplan with 14 'Ceilings and a 10' tall pocketing sliding glass door to the expanded lanai complete with outdoor kitchen, oversized pool infinity spa, waterfall, spacious deck space. Enjoy your meal with fully equipped outdoor kitchen at sunset…brThe accommodationbrA VACATION LIFESTYLE IN ESPLANADE! Situated in north naples Florida, short ride to the shopping, fine dining as well as to the beautiful sugar white sandy beach, this Stock built FULL GOLF MEMBERSHIP HOME (4+Den/4.5BA/2 Car) offers a grande great room style floorplan with 14' ceilings and a 10' tall pocketing sliding glass door to the expanded lanai complete with outdoor kitchen, oversized pool infinity spa, waterfall, spacious deck space. Enjoy your meal with fully equipped outdoor kitchen with a glass wine…brEsplanade is a true LifestylebrCommunity with something for everyone: Resort Pool complete with cabanas and beach entrance; 6 tennis courts; 4 bocce ball courts; 4 pickleball courts; Koquina Day Spa offering hair, nail, facial, and spa treatments; Techno Gym with AerobicsbrRoom; gated dog park; Poolside Bahama Bar; 14 miles of bike/walking trails; 18 hole private golf course (can use your own cart); 15,000 Sq Ft Culinary Center featuring restaurant, bars, wine tasting room, wine lockers, & Starbucks style cafe!brAccess for guestsbrA VACATION LIFESTYLE IN ESPLANADE! Situated in north naples Florida, short ride to the shopping, fine dining as well as to the beautiful sugar white sandy beach, this Stock built FULL GOLF MEMBERSHIP HOME (4+Den/4.5BA/2 Car) offers a grande great room style floorplan with 14' ceilings and a 10' tall pocketing sliding glass door to the expanded lanai complete with outdoor kitchen, oversized pool infinity spa, waterfall, spacious deck space. Enjoy your meal with fully equipped outdoor kitchen with a glass wine…brEsplanade is a true LifestylebrCommunity with something for everyone: Resort Pool complete with cabanas and beach entrance; 6 tennis courts; 4 bocce ball courts; 4 pickleball courts; Koquina Day Spa offering hair, nail, facial, and spa treatments; Techno Gym with AerobicsbrRoom; gated dog park; Poolside Bahama Bar; 14 miles of bike/walking trails; 18 hole private golf course (can use your own cart); 15,000 Sq Ft Culinary Center featuring restaurant, bars, wine tasting room, wine lockers, & Starbucks style cafe!brOther important informationbrRegarding using the Golf membership: After your booking, we submit signed lease with application that transfers the owner's golf privileges to renters. We give esplanade permission to issue up to 2 car passes for gate access for tenant use. Esplanade one time fee is $600. Please kindly remember for this application we Must submit paperwork at least 1 month prior to move in.

Stunning Upscale 4B\5Bath Villa With Full Amenities And Golf Membership

Naples, Florida, United States

Bed

Bath

Sleeps

$240.08

Reviews on homeaway.COM. Our Villa (detached house) is nestled in a very private deed restricted community. Our Villa boasts four bedrooms (two of them suites) and a den, besides the great room with huge vaulted ceilings, the very large kitchen, separate dining area and a Den. A heated swimming Pool/Spa on the covered Lanai & private garden + fruit trees. It has all the needed amenities such as 3 full bathrooms, a washer/dryer room, PC + High Speed Internet, phone Cable etc. Every room has large screen plasma TV/DVD Player. Under 4 miles to the Beach (actual feet in the sand), and just 3.2 miles to 5th Avenue South. All else is walk to. Everything provided even beach lounges. brbrWe have recently upgraded the home again!brbrSubzero built in 48 inch side by side refrigerator, GE monogram PRO double ovens, Wolfe 36 inch cooktop, European Bosh dishwasher, are the appliances.brbrThe kitchen cabinetry was custom made just for us on the spot. Two tone with white uppers with chocolate glaze, and cherry lowers. The cabinets are taller for comfort and there are only deep drawers so no need to get on the floor to dig for lower pots and pans. Adorning the cabinetry is exotic granite (called TajMahal).brbrThe home is professionally decorated and contains many pierces of commissioned art, and antiques.brbrSome of the designer names you will find in our home include, Ralph Lauren, Armani Casa, Theodore Alexander, Maitland Smith, Christopher Guy, Marge Carson, Century custom made Top leather seating, Baker, Robb & Stucky and more. There is crystal by Swarovski, Waterford, and Mouth blown Italian crystal. The lighting both inside and out was done by a famous lighting artist.brbrCustom Italian floors, Imported front entrance medallion, Spanish imported tile works, custom lighting by one of the premier lighting artists in Naples.brbrAnd on and on…br

2 Master Suites Beach Villa with Heated Pool/Spa Private Community

Naples, Florida, United States

Bed

Bath

Sleeps

Exceptional(13)

$268.14

Two Bedroom Unit overlooking the pool at Bayshore Inn & Docks. One bedroom is a Queen bed, the other bedroom has two Twin beds. Living room with smart tv and fold down couch. All tile bathroom with shower. Kitchen with fridge, microwave, two burner stovetop (no oven), dishwasher, and coffee maker. Unit also includes access to Bayshore Inn & Docks amenities including the heated pool, grill, screened in lanai overlooking the canal and beautiful sunsets as well as the docks with availability for boats to use. The canal has access to the Gulf with no bridges.

Bayshore Inn & Docks Two Bedroom Unit 8 Overlooking the Pool

Naples, Florida, United States

Bed

Bath

Sleeps

$179.48

Unwind in Naples at this luxurious villa featuring two bedrooms with a king and a queen bed, plus an additional office space that includes another queen bed. The villa offers two bathrooms, each equipped with a with everything you need for your comfort. The home is complete with brand new, high end furnishings, all you need to bring is yourselves! Two car garage includes an EV charger, beach chairs, beach umbrellas, and more! Guests can enjoy a tranquil atmosphere perfect for relaxing or working remotely. Enjoy your coffee or tea outside on the lanai, or grill on the brand new state of the art bbq, while you enjoy the peaceful surroundings. Naples Reserve is a beautiful gated community with resort like amenities including a pool, tiki bar, boat launch, stand up paddling, kayaking, full gym, community activities, and more! Whether you’re lounging indoors or enjoying the amenities, this enchanting space provides a peaceful retreat. We hope you'll enjoy your stay at our villa! HOA approval required! Thirty day minimum; accepting seasonal and annual inquires (annual offered at discounted rate).

Luxurious 2+ BR villa:highly sought after Naples Reserve for annual & seasonal

Naples, Florida, United States

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Bath

Sleeps

Select Dates for Price

Nestled in Naples, this delightful villa offers a fantastic retreat for guests. With 8 bedrooms including 3 king beds on the first floor and 5 queen bedrooms on the 2 nd floor. There are 9 bathrooms featuring luxurious amenities like a jetted bathtub and bidet. The outdoor bar seats 10 with plenty of room to entertain. Pets are welcome. Come experience all that Naples has to offer with a stay at our villa!

Naples Villa on the Golf Course! 8 Bedrooms Sleeps 20! Pets welcome, 30 day min

Naples, Florida, United States

Bed

Bath

Sleeps

Exceptional(2)

$127.68

Welcome to our charming retreat, a serene and beautifully appointed home nestled just 2 miles away from the sun-kissed beach. This idyllic location is perfect for those who enjoy the vibrant beach life, 5th Ave shopping and tons of restaurants. Naples Pickleball Center with 66 courts is a 10 minutes drive away or the Botanical Garden. brbrIt is located in a quiet and secluded neighborhood. The home was completely renovated in 2024. The house offers 2 bedrooms with queen beds, 2 bathrooms, living room, kitchen, patio enclosed, outdoor seating. brbrAs you step inside, you will find a tastefully decorated interior that exudes comfort and style. The living space is designed for relaxation and social gatherings, featuring cozy seating, a flat-screen TV, and ample natural light. The adjoining dining area is perfect for enjoying meals together, whether it is a quick breakfast before heading out to explore or a leisurely dinner. Our kitchen is fully equipped with modern appliances, cookware, and utensils, making it easy to prepare your favorite meals. The bedrooms offer a peaceful escape at the end of the day, with comfortable beds and soft linens ensuring a restful sleep. brbrOutside, the property boasts a lovely patio area where you can enjoy your morning coffee or evening cocktails. The backyard is spacious and perfect for outdoor activities or simply soaking up the Florida sunshine. brbrThings to do nearby: brbrBEACH DAYS: Clam Pass Beach Park, Lowdermilk Park, Public Beach, Via Miramar Beach, Barefoot Beach Preserve Park, Bonita Beach Park, Lovers Key Beach. brFAMILY FUN: Naples Zoo at Caribbean Gardens, Coral Cay Adventure Golf, InPlay!, Naples Pier, Golisano Children's Museum of Naples, Sun-N-Fun Lagoon. brTHINGS TO SEE: Freedom Park, Tin City Waterfront Shops, 5th Avenue Shopping, Downtown Naples, Naples Botanical Garden, The Wonder Gardens, Bird Gardens of Naples. HIT THE LINKS: Grey Oaks Country Club, Naples Grande Golf Club, Tiburon Golf Club, Arrowhead Golf Club, Bonita Fairways Golf Course. brbrHOA requires an application form, signed rental agreement, br$100 application fee, and background check.

Charming Florida home: only 2 miles to the beach and 5th Ave

Naples, Florida, United States

Bed

Bath

Sleeps

Exceptional(12)

$370.76

This home is the picture of relaxation, fully equipped with everything you may need for a comfortable stay; a large kitchen with beautiful granite countertops and stainless steel appliances, we have over 10 parking spaces in the driveway and 2 cover garage parking spaces. Beautifully remodeled home with 3 bed 2 baths plus an amazing TV room that can be use and an extra bedroom.brLocated in a charming residential neighborhood with over 2 acres and diversity of fruit trees!brReverse osmosis water filtration system for the whole house and also a special one under the kitchen sink, enjoy bottled quality water by using the water spout on next to the faucet. brYou will have full access to everything in our home, we ask you to treat our home with respect as you would treat your own home.brLet this Naples home be your little slice of paradise. The location is phenomenal for golfing, wine tasting, beaches and nearby nature walks. And the home itself is beautiful with plenty of relaxing amenities. brWe live and work locally, so we are able to provide any services whenever necessary.brWe’re located only 8.0 miles away from Clam Pass Beach. Naples, Florida has been rated as the happiest, healthiest city in the United States for 3 years in a row. Parties and events are not allowed. extra fees may applied if rules are broken.

La Finca... Beautiful Countryside Home

Naples, Florida, United States

Bed

Bath

Sleeps

$205.35

Greenlinks is a sought after community in the popular section of Lely in Naples. Two bedrooms and a den with a sleeper couch, two full bathrooms and a large lanai overlooking the lake is the perfect way to spend your winter in SWFL! Fully furnished and equipped - ready for your vacation getaway. Amenity rich and located just a few miles to downtown and beautiful beaches. Activities include 2 tennis courts, pickle ball court, shuffleboard, bocce ball, a beautiful resort style swimming pool, spa and clubhouse with a fitness center. Inquire about our shorter term rentals of 3-7 days. Golf is available - rates vary. Off season guests get two free golf passes.br

623 Changes in Latitude - Greenlinks at Lely resort in Naples, FL

Naples, Florida, United States

Bed

Bath

Sleeps

Exceptional(6)

$176.41

Spacious, newly renovated end unit in gated community walking distance to the beach. Pool and hot tub with inside controls, enclosed lanai overlooking water views. Two BR, two full bath, open spaces abound. Two car garage. Great opportunity for seasonal or annual rental in beautiful north Naples! Annual and 3-month rentals also available, contact owner for details. Turnkey, fully furnished. For seasonal rental (6 mo.), owner pays pool maintenance, electricity and basic cable.

Steps to the beach, renovated villa with private pool / spa, gated community

Naples, Florida, United States

Bed

Bath

Sleeps

Exceptional(8)

$623.05

Luxurious 3 bedrooms with 2 full bathrooms 2365 Sq ft villa. brbrThis sunny east facing villa with a large lanai located in the exclusive gated community of Windstar Club on Naples Bay. Minutes from downtown Naples, and only 1 minute from the Botanical Gardens and USA Open Championships pickleball courts. brbrComfortably furnished, and fully equipped home. Attention to detail is important to us, we provide a very clean comfortable home for an unforgettable experience. New Daikin silent air conditioner with Daikin Premium Air Cleaner Cabinet, installed in July 2024. brbrThis is not an income property! We only rent out this home when we are staying at our home in Europe or South Africa. We are particular who we rent to, because we would like to ensure that our beautiful home is appreciated. brbrFor the entire duration of your stay the villa will be thoroughly cleaned once a week by a professional cleaning service. brbrLarge sunny open-planned living room with 15 foot vaulted ceilings. Large new Samsung 77-inch OLED TV installed January 2025 includes cable with all channels and includes Netflix - Peacock - Britbox and DVR with on demand movies. Total of 4 TV's in home.brbrThe chef’s kitchen. Fully equipped large modern chef's kitchen with large windows built in appliances and every conceivable small appliance available.brbrTwo 6 seater dining tables one inside in the dining area and the second on the lanai. brbrEnjoy cocktails and dining in the wonderful Naples sunshine on the large lanai. Comfortable lanai with 3 motorized screens with remote, and a fully equipped built-in outdoor kitchen with a fridge, sink, 3 BBQ's, wood or charcoal and propane, and a large professional extractor hood with two blowers. Lanai with 15 foot vaulted ceilings also includes comfortable lounging couches with a coffee table for 6 and a second dining table for 6. brbrThe master bedroom has a king bed suite with a very comfortable mattress, With 15 foot vaulted ceilings, walk-in closet, large TV, and a large bathroom with a large walk-in shower and twin vanities and a bathtub. The guest bedroom has a king-bed suite with a comfortable mattress, and a full bathroom with a walk-in shower. brbrThe third bedroom does not have a bed. This room is being used as an office only, and equipped with fast Wi-Fi covering the entire home. Office has a large monitor, printer, copier and a shredder. brbrSeparate laundry room with washer and dryer, sink and cupboards. New Samsung washer and dryer insatlled March 2025.brbrDouble garage with remote garage door and another stainless-steel French door fridge-freezer. brbrComfortable lanai with 3 motorized screens with remote, and a fully equipped built-in outdoor kitchen with a fridge, sink, 3 BBQ's, wood or charcoal and propane, and a large professional extractor hood with two blowers. Lanai with 15 foot vaulted ceilings also includes comfortable lounging couches with a coffee table for 6 and a second dining table for 6. brbrWindstar is a private gated community nestled along two miles of Naples Bay eastern shoreline frontage. With sprawling 550 acres, the community offers an impressive selection of amenities 18-hole Tom Fazio championship course, tennis courts, and an exquisite new clubhouse that features dining and stunning sunset views on Naples Bay. Windstar Southpointe Marina has 72 slips and can accommodate yachts up to 70 feet. brbrWindstar Club is a private members-owned club renters have no access to the club unless invited by a member. brbrRenters can take the Windstar Club Keewaydin Queen shuttle to Keewaydin Island beach-club where Windstar Club has a private beach and dock or take the sunset cruise. brbrNaples, with its beautiful white sandy beaches and many attractions, is a sought- after destination to live and vacation. The newly built Naples Philharmonic in 2024, visit the Naples Zoo, airboat rides in the Everglades, swimming, shelling, tennis, pickleball or golf, deep sea fishing or in the Everglades waterways, bicycling or paddle-boarding. Naples's 5th Ave and 3rd St for shopping with exceptional fine dining restaurants, all that makes Naples in Southwest Florida one of the most desired destinations. brbrThere are also several really good breakfast, lunch, dinner, brewery and coffee shop options right on Bayshore Drive, all within 1 minute by car from the Windstar front gate. Seventh Street South new waterfront restaurant and drinks bar opened June 2025. Ankrolab Brewery with food truck - Rebecca's wine bar and restaurant - The Med Italian - Mojitos Mexican - Celebration Park food truck park with large open-air bar right on the water also accessible by boat - Real McCaw bar and dining - Bayshore Coffee - Botanical Gardens restaurant. Downtown Naples shopping and dining are only 5 minutes by car. 50 new restaurants are opening in Naples in 2025.

Windstar an exlusive community on Naples Bay! Well appointed 3 bed 2 bath villa

Naples, Florida, United States

Bed

Bath

Sleeps

Exceptional(18)

$245.31

Golfers dream! Recently updated Villa. Country club setting with Sam Snead's restaurant and bar overlooking the two public golf courses. During the period of May 15 through October 15, I provide free greens(cart not included) fees to the Lely Golf Courses. Green fees must be requested during reservation confirmation. Tee times must occur through the Greenlilnks Club House and not directly with the golf course management and are subject to availability. You may also use my discounted green fees to Lely golf course any time.brbrIn addition, Greenlinks club house is a great meeting place. Amenities include: 36 holes of golf on a championship designed golf course. Large resort-style pool with waterfalls, Jacuzzi hot tub, additional lap pool, tennis courts, BBQ grill's, fitness facilities, 2 tennis courts, pickleball court, shuffleboard, bocce ball, beautiful resort style pool, spa and concierge services. Also, close to Marco Island and downtown Naples and the beautiful Naples Beaches.brbrDuring the period of May 15 through October 15, we will provide two free greens (cart not included) fees to the Lely Golf Courses. Green fees must be requested during reservation confirmations. Tee times must occur through the Greenlilnks Club House and not direct with the golf course management and are subject to availability. Villa is complete with all amenities including washer/dryer. Villa is complete with all amenities you could possibly need. Living Room, Office area, Den, Kitchen, Dining, large outdoor area overlooking lake and pool. master bedroom with king size bed and large master bath with soaking tub. 2nd bedroom has 2 twin beds, Den has queen- size-pull out bed. Beautifully updated, with lots of sunlight. Sleeps 6. Weekly and monthly rates available upon request.

Naples, FL. Lely Resort Gorgeous 2 bed, plus den sleeps 6. Free Golf till 10/15

Naples, Florida, United States

Bed

Bath

Sleeps

$358.9

Large 3 bedroom 3 bathroom town house located in the luxurious Fiddlers Creek. The living area, dining room, family area, and bedrooms have all been tastefully decorated and are all fully furnished. The master bedroom is large with an impressive master bathroom attached. The guest bedrooms are spacious and have there own bathrooms. The kitchen has a great layout with plenty of room to cook, and there is a breakfast bar attached. There is a lanai out back that faces a pond and plush green grass. The Montreux community has its own pool for owners and guests. The Fiddlers Creek clubhouse is extremely impressive including a resort style pool & hot tub, tiki bar & grill, tennis & pickle ball, and a state of the art gym.

Luxury Living In Fiddlers Creek

Naples, Florida, United States

Bed

Bath

Sleeps

Exceptional(2)

$153.57