Vacation Condo Rentals By Owner In Naples, FL

$706.7

Seasonal - Annual - Monthly Steps from Beach and Shopping

Naples, Florida, United States

Upstairs Unit -- No Pets Available for 30 Day Rentals Only - Total 90 DaysbrThis 2 bedroom 2.5 bath unit is located on the second floor with a private balcony and private glassed front porch. The unit features a cottage theme with all-white furniture in the kitchen and living areas, an office, one king bed, and one queen. The kitchen is fully equipped with a toaster, coffee maker, pots, pans, dishes, glassware and silverware. All linens are furnished. All furniture is new. Laundry in unit.brbrThe quaint building is home to 4 units all with private entrances. It is located on Second Street South, a quiet residential side street in Old Naples. The stroll to the beach is 3 minutes, 5th Avenue 5 mins, and Third Street South 10 mins. Bike rentals and golf cart rentals are available. This host provides concierge services upon request and for an additional charge. brbrStroll along the streets and avenues of Historic Downtown Naples, FL. where you’ll find more than 100 unique shops and boutiques, art galleries, theaters, and fine restaurants tucked between historic buildings and beautiful courtyard gardens. brbrThe pedestrian-friendly setting offers a dynamic shopping experience that is anchored by the 5th Avenue South and Third Street South districts. Just steps from the Naples Pier and Historic Palm Cottage (the oldest home in Naples), and the Third Street South shopping district. As you wander up and down the street, you will find lovely shops and delightful outdoor cafes. The area also has a large number of art galleries; boasting more than anywhere else in Southwest Florida. Third Street South has been a hub of fashion and entertainment since the 1930s and has maintained a unique charm that you cannot find in modern shopping developments. On Saturdays, they host a farmers market that is brimming with locally grown produce and flowers alongside handmade soaps and other craft items. Thursday evenings are a special treat in the Third Street South and Fifth Avenue districts, as the area comes alive with music and entertainment. For information on upcoming events be sure to check with the Third Street South and Fifth Ave Concierges.brbrParking is allowed on the streets of Naples and Beach Parking is available by the meter.

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4

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$229.4

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Charming 2-bedroom condo with WiFi, AC in delightful Naples

Naples, Florida, United States

Nestled in The Glades Country Club in Naples, this delightful 2 bedroom/2 full bath, single story condo boasts both front (2) and rear patios, including an air conditioned lanai. Guests can enjoy amenities like a Wifi/Cable TV (including HBO), full washer/dryer and all the amenities that The Glades Country Club has to offer (multiple pools, golf courses, pickle ball, tennis, bocci ball etc). Experience a marvelous stay in this fabulous property, perfect for a relaxing getaway. We hope you enjoy what our place and Naples has to offer.

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2

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4

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$246.05

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Charming 2-bedroom condo with WiFi, fitness room in nice Naples. Golf available.

Naples, Florida, United States

Welcome to this charming condo in Naples. This lovely property features 2 bedrooms - one with a king bed and the other with 2 twin bed. You'll also find 2 bathrooms with shower amenities. Additionally, there's an adorable office space with a comfy sofa bed. Guests can enjoy WiFi, a hair dryer, AC, and access to a fitness room. We look forward to hosting you at our place.

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$195.66

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G-144 - First Floor - End Unit With Lake Views!

Naples, Florida, United States

Summary:brbrWe are located in a 13-acre subtropical oasis in the heart of Naples, FL very close to downtown and within a short drive of 9 miles of beaches! Our on site amenities include a heated pool, a restaurant serving lunch and dinner equipped with a full bar, a BBQ deck with a Gazebo, and tennis and pickleball courts.brbrbrbrThe Space:brbrWelcome to Park Shore Resort Naples, a tropical hideaway within a 13 acre subtropical oasis in the heart of Naples, Florida. Situated amid serene waterways and lush greenery, our resort offers a tranquil escape that feels miles away from the everyday hustle and bustle. brbrbrbr*Your accommodations include 2 Queen beds and a sleeper sofa along with 2 full sized bathrooms to accommodate 6 peoplebrbr*Guests can walk right out to the path that leads to the amenities from the first floor lanaibrbr*This condo is and end unit- with no neighbors on one side and extra light from an additional window.brbr*Guests can use the full sized washer and dryer located inside of the condo brbr*There is casual indoor dining for 6 and enjoy outdoor meals on the lanai and at the grilling gazebobrbr*Parking is available throughout the resort including just outside the condo brbrThere is a maximum of 6 guests allowed per reservation. Occupancy is strictly enforced. brbrbrbrResort Features and Amenities: Stylish Accommodations: Our condos are designed with comfort and style in mind, providing a perfect retreat for relaxation. Every unit is marketed individually and the photos that you see are the exact unit that you will be renting and the views from the units all vary. brbrbrbrHeated Swimming Pool: Dive into our heated swimming pool or relax poolside with lounge chairs and umbrellas, perfect for soaking up the Florida sun. Enjoy the sights and sounds of a waterfall behind the pool deck. brbrbrbrSports Facilities: Stay active with our diverse range of sports amenities. Enjoy a game of tennis on 2 courts or pickleball on 6 courts. We also have beach volleyball, a basketball hoop and racketball. brbrbrbrFitness Center: Keep up with your workout routine in our fully-equipped fitness center located in the lobby. Lakefront Walking Paths: Stroll along our scenic walking paths that wind around the central lake and enjoy watching our native wildlife including turtles, fish and wading birds that call the lake home. brbrbrbrIsland Gazebo & Barbecue Grills: Enjoy a leisurely barbecue at our island gazebo, complete with grills for guest use so you don’t have to eat out every night if you don’t want to. Cheeseburger in Paradise, anyone brbrbrbrOn-Property Dining at Hogfish Harry's Restaurant & Bar: Savor delicious meals at Hogfish Harry's with a full bar and delicious seafood. Whether you choose to dine indoors or al fresco with views of the pool and waterfall, you’ll enjoy a meal with a view. Take out is available too! brbrbrbrGuest Services and Conveniences: Our guest services desk is open from 7am to 11pm, ensuring you have everything you need during your stay. brbrbrbrAccessible Amenities: We are committed to providing accessible facilities to ensure a comfortable stay for all our guests. Check out our Resort Accessibility Map for more details.brbrbrbrTo give our guests flexibility and peace of mind, we offer two ways to cover accidental damage during your stay. Choose either a $20 non-refundable damage fee or a $500 refundable hold. This payment is collected after booking and before check-in. brbrbrbrLocal Attractions: Centrally located yet secluded on lush, private grounds, Park Shore Resort is the ideal Naples, Florida vacation spot for relaxation and comfort. The resort is walkable to some local shopping, dining and multiple grocery stores and about a 12 minute drive (4.4 miles) to downtown Naples. Horizon Way (1.8 Miles) and Seagate/North Gulfshore Beach (2.0 miles) accesses are the closest beaches to the resort. Another favorite spot is Venetian Village (1.2 miles) with waterside shopping and dining. Waterside Shops (0.9 miles) is a luxury shopping mall just a few miles away and you can enjoy nightlife or a movie at The Mercato (3.9 miles) or the Pavilion (3.7 miles)brbrbrbrImportant Details: This condo and the on site rental program is managed by SW Florida-based Mike Z Rentals LLC. We have a staff member available at the front desk from 7 am until 11 PM as well as a 24/7 call center, a reservations manager and guest services manager along with a professional cleaning partner to take care of all your needs while you are staying in this property. Park Shore Resort is 30 miles from RSW - Fort Myers International Airport and the closest exit to I-75 is Exit #107 - Pine Ridge Road.

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$156.16

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HERITAGE BAY GOLFER'S PARADISE! Luxury Condo in Naples w/AMAZING AMENITIES

Naples, Florida, United States

Vacation in a tropical paradise, resort-style gated community of Heritage Bay Golf and Country Club! The resort features a premier 27 hole Lewis-Azinger championship golf course, 6 lighted Har-Tru tennis courts, pickleball, bocce, zero-entry resort pool with waterfall and a lap lane that has several firepits around the pool and view of aqua driving range, activities director, full-service gorgeous Cabana bar and grill by the pool with live entertainment weekly, fine indoor/outdoor dining at the beautifully renovated clubhouse (GREAT FOOD at both restaurants), state of the art fitness center & spa offering exercise classes, and pro shop. If you prefer a quieter setting, there is a satellite pool just across the street from the condo. There is so much to do inside the resort, but the great location is just 25 minutes to Gulf of Mexico beautiful beaches, SW Florida airport, and downtown Naples, with many restaurants and shopping located close by. Your accommodation is a Luxury condo, approx .1232 sq. ft., 2 bedroom 2 bathroom and with its top quality furnishings is the very best one you will stay in at the resort. The condo has a bright open layout located on the 3rd floor (elevator access) and has a panoramic view of the golf course, water, and nature preserve. You will love the VIEW and peacefulness of sunsets from your screened in lanai. It has a washer and dryer, fully stocked kitchen with stainless steel appliances, formal dining table, breakfast dining table, lanai dining, 3 cable tv’s and Internet, a king bed in the primary bedroom and a king bed in the guest bedroom, a shower in the primary bathroom and a shower over tub in the guest bathroom, and the most comfortable suede leather reclining couches in the living room. Both bedrooms have new luxury vinyl flooring and tile is throughout the rest of the condo. Just pack your clothes, toothbrush, and golf clubs. You will be able to store you suitcases, golf clubs, and bikes (if you bring them) in our storage closet and park your car in the covered carport directly below the condo. All the wonderful resort amenities are yours during your stay for a fee of *$500 DURING THE LENGTH OF YOUR STAY. Minimum rental period is 30 days (excluding February). HOA needs approx. 30 days to approve application, so please complete the paperwork as soon as reservation is booked. Go to https://www.golfheritagebay.com/ to see a great video of the Heritage Bay amenities. *Fees explanation that are paid by you AFTER BOOKINGt: $50 non-refundable application fee (administrative fee), $500 transfer of membership/amenities fee. This property is new for us, but we are Super Hosts with another property, 4.9% overall satisfaction rating out of 68 stays. We strive for perfection!

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$415.86

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Enjoy great pool views from this 3 bedroom condo - CL0201

Naples, Florida, United States

Naples Cay is the finest beach front community to spend your next vacation. The Club 201 is a 3 bedroom, 2 bath condo with a view of the pool from the spacious lanai. You will be just a short walk away from our private beach, for which we provide you with beach chairs and an umbrella for your convenience. Equipped with a full size and fully stocked kitchen, we provide you with everything you need to prepare delicious meals. The large dinning room table and bar stools allow the whole family to gather for any meal. The Primary bedroom has an ensuite bathroom and walk in closet. The bathrooms are updated with tile showers and granite countertops. This unit also provides a washer and dryer in unit for your use while staying. We hope you enjoy this amazing place as much as we do. brbrNaples Cay, a 24 hour gated community, you will enjoy a heated community pool, hot tub, fitness center with sauna and steam room, and har-tru tennis courts. A boardwalk takes you to the private white powder sand beach. This premier beachfront location is close to Venetian Village and the Waterside Shops where you will find many upscale restaurants and shops as well as the Artis, Naples premier performing arts center. Naples Cay now features 2 EV Car Charging Stations. Located in the parking lot east of The Club building. An account must be set up through Sema-Connect for payment.brbr***All reservations made between January 1 and April 30 must be Saturday to Saturday. Please inquire for special requests.*** brbrPlease Note: Roof replacement will occur mid-June to mid-July 2024.brbrFor more information on Naples Florida vacation rentals or monthly rentals in Naples Florida, please contact us at 1-.brbr***Information contained herein deemed reliable but not guaranteed**brbrAmenities Include:brbr- Bldg. Complex Name: Club @ Naples Caybrbr- Type Unit: Highrise Condobrbr- Unit Rating: Silverbrbr- Beach Access Type: Walk to Beachbrbr- Distance to Beach: 150 yardsbrbr- Elevator: Yesbrbr- Floor/Bldg Height: 2/14brbr- Year Built: 1990brbr- Approx. Sq. Ft.: 1445brbr- Exposure/View: West/gulf coastbrbr- Pool/Spa: Yes/Yes Communitybrbr- washer dryer: Yesbrbr- Parking Type: Openbrbr- Lanai / Balcony: Open Balconybrbr- Bbq Grill: Yes communitybrbr- Master Bedroom: Kingbrbr- Bathrooms-Master: Showerbrbr- Guest Bedroom: Queenbrbr- Bathrooms-Guest: Tub/Shower combobrbr- Guest Bedroom 2: 2 Twinsbrbr- Internet Access: Wifibrbr- Listing Advisor: Weekly Divisionbrbr- Min. Rental # x perYr: 7x52brbr- Reservation Fee: $170brbr- Damage Protection: $60brbr- Application Fee Req.: $150brbr- Departure Clean Fee: $200brbr- Taxes: 11%brbr

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$579.92

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Beachfront Paradise with Stunning Gulf Views – Your Naples Escape Awaits!

Naples, Florida, United States

Wake up to the soothing sound of waves and breathtaking Gulf views from this beautiful 2-bedroom beachfront condo in Naples. Perfect for a peaceful getaway, this charming retreat offers a luxurious gulf side primary bedroom, and a second bedroom with a full bed, and a twin —ideal for families or couples seeking comfort and serenity. Step onto the private balcony to watch the dolphin and the sunset over the water, or take a few steps to the sandy shores for a morning stroll. The unit has everything you need including beach towels. The fully stocked kitchen is perfect for preparing your meals and hosting some new friends from the building. There are two laundry rooms per floor. Conveniently located to shopping and restaurants.brbrRental PolicybrMonthly rentals only – as required by the HOA.brStays must begin and end within the same calendar month.brFlexible monthly rates depending on season.

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6

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$163.14

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Sophisticated Naples Getaway – Relax in Style

Naples, Florida, United States

Step into this elegant 2-bedroom, 2-bath condo and feel instantly transported to your personal Naples sanctuary. Bathed in warm Florida sunshine, the open-concept living area is perfect for unwinding after a morning of exploring or enjoying cozy evenings with family and friends. Every corner of the space is thoughtfully designed with comfort and style in mind, making it easy to relax, connect, and enjoy the slower pace of coastal life.brbrThe fully equipped kitchen invites you to prepare fresh meals, gather around the dining area, and toast to the start of another sun-soaked day. The primary suite offers a private escape, complete with a spa-like bath and serene touches that make it feel like your own personal retreat. The second bedroom is equally inviting, ideal for guests or family members seeking comfort and privacy.brbrOutside, the community pool beckons for a refreshing swim or a leisurely lounge under swaying palms. The lush landscaping and tranquil surroundings provide a peaceful backdrop for your mornings with coffee or afternoons with a good book.brbrPerfectly situated just minutes from Naples' renowned 5th Avenue South and 3rd Street South, you're close to world-class shopping, dining, and entertainment, yet tucked away in a quiet, intimate community. Whether you're seeking a romantic getaway, a family adventure, or a sun-filled escape with friends, this condo promises a luxurious, unforgettable Naples experience where comfort, style, and relaxation come together.brbrASSOCIATION APPLICATION/FEE: An application and/or background check may be required for rentals within the community. This may incur processing fees not included in the rental reservation.brbrBOOKING DETAILS: A 2 month minimum is required.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.

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$184.21

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Luxurious Naples Retreat – Steps from Dining & Shopping

Naples, Florida, United States

Escape to Port au Villa, where sophisticated coastal living meets the ultimate vacation experience. This beautifully updated end-unit condo offers a serene and sun-filled sanctuary, perfect for relaxing mornings, leisurely afternoons, and unforgettable evenings in Naples.brbrThis spacious two-bedroom, two-bath condo features an open-concept living area filled with natural light, a fully equipped chef's kitchen with high-end finishes, and a beautifully appointed primary suite offering a tranquil escape with an ensuite bath and inviting design touches throughout.brbrStep outside to the sparkling waterfront pool, surrounded by lush tropical landscaping, and watch the boats glide by as you soak in the tranquil ambiance.Enjoy a morning coffee or an evening glass of wine while taking in the peaceful water views and gentle coastal breeze.brbrPort au Villa's intimate boutique community offers the perfect balance of privacy and convenience, just moments from Naples' premier shopping, dining, and entertainment along 5th Avenue South and 3rd Street South.brbrWhether you're seeking a peaceful retreat or an indulgent getaway, this Naples condo delivers an unmatched coastal escape filled with comfort, style, and memorable experiences.brbrASSOCIATION APPLICATION/FEE: An application and/or background check may be required for rentals within the community. This may incur processing fees not included in the rental reservation.brbrBOOKING DETAILS: A 2 month minimum is required.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.

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4

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$164.19

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Full Golf Privileges + Resort Perks in Naples' Coveted Treviso Bay

Naples, Florida, United States

Experience the pinnacle of Naples resort-living in this exquisite 2-bedroom, 2-bath condominium located on Giaveno Court in the gated, guard-gated Treviso Bay community. This unit comes with a transferable, full golf membership to TPC Treviso Bay, granting tenants the rare privilege of enjoying championship golf privileges right at home.brbrKey Features & Highlightsbr • Golf Privileges: This home carries a transferable, full TPC golf membership, an additional $250 — giving you access to the 18-hole Arthur Hills–designed championship course, pro shop, practice facilities, and clubhouse amenities.br • Upscale, Open Plan Interiors: Light-filled living and dining areas flow seamlessly, ideal for entertaining or relaxing.br • Gourmet Kitchen: Equipped with high-end appliances (stainless steel), granite/quartz surfaces, custom cabinetry, and a generous breakfast bar or eat-in nook.br • Master Suite & Guest Suite: The master offers a private bath and walk-in closet; the guest bedroom is paired with a full guest bath.br • Lanai & Views: Enjoy tranquil views over the lake, preserve, or fairways from the screened lanai — the perfect spot for morning coffee or evening sunsets.br • Convenience & Storage: Covered/assigned parking & private storagebrbrCommunity & Resort-Style Amenitiesbr • Two clubhouses (including the 64,000 sq ft main clubhouse and a secondary relaxation/spa house) br • Resort-style lap pools, lagoon pools, poolside dining & barbr • Full spa, fitness center with classes, aerobics/Pilates studiobr • Tennis, pickleball, bocce, and walking/biking trailsbr • Social and dining venues, lounges, events rooms, business center, librariesbr • 24/7 security and gated accessbrbrLocation & LifestylebrbrSituated just minutes from downtown Naples, premier shopping, fine dining, and the pristine Gulf beaches, this condo offers both tranquility and convenience. The Treviso Bay address places you ideally between Naples and Marco Island for the ultimate Southwest Florida experience.

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4

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$173.9

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US NEWS Ranking: Naples # 1 city to live in 2025/2026. Beautiful condo for rent.

Naples, Florida, United States

Welcome to Naples, Florida, Voted #1 best places to live by US News 2025/2026.brbrExquisite 1,250 square 2 bedroom 2 bath condo in Treviso Bay. Just 8 miles to the Naples Pier/beach and downtown Naples. The condo is professionally decorated and is located on the 1st floor. The living room extends to the lanai with stunning daytime and sunset views of one of Treviso's beautiful lakes and Rookery Bay. A luxurious, quiet swimming pool and BBQ grill are located within a short walking distance of the condo. The community has 24 hour manned security gate and is beautifully landscaped throughout the entire area. brbrA Social Membership is available and gives tenants access to all the wonderful resort style amenities that Treviso Bay has to offer: lagoon and lap pool, the Villa Rilassare Club with an outdoor restaurant and bar; 8 har-tru tennis courts, bocce ball, basketball court, spa, fitness center/ classes, and cabanas at the main pool. Pickleball is also within the gates of Treviso Bay. There is also a 55,000 square foot clubhouse that provides incredible dining, enjoyable social events, lunch, library, game/card room, concerts and a variety of entertainment. brbrThe condo is also available for golf during the off season with a transferable golf membership. The golf will also be available during some months of the winter season. (Contact owner for available months.) 913-706-7028brPictures of Treviso Bay can be found at www.TPCtrevisobay.combrbrPLEASE NOTE: annual, monthly and seasonal rates vary. Annual rental will be at a lower rate.

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6

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VANDERBILT BEACH-RARELY AVAILABLE PENTHOUSE UNIT - GORGEOUS VIEWS OF BEACH/BAY!

Naples, Florida, United States

Vanderbilt BeachbrUnit 1201-Penthousebr11030 Gulf Shore DrivebrNaples, Florida 34108brbrA one-of-a-kind, extensively renovated Penthouse unit that encompasses the entire top floor offering sweeping vistas up and down the crescent coast with dramatic Gulf and Bay Views. This 3 bedroom, 3 bath condominium unit has a total square footage of 3,200 including outdoor space and must be seen to be appreciated. You will have some of the best views in Vanderbilt Beach with its 42’ Western facing balcony and wraparound deck. The recent renovation completely reimagines this unit with an open floor-plan and new kitchen, giving it a finish and feature quality to match the breathtaking vistas. Updates include a double entry door, wood tile flooring throughout, linear diffusers, impact windows, electric blinds, custom lighting, updated mechanicals, updated baths, gourmet kitchen and more!brLuxury amenities include 1st floor private cabana, two reserved and covered parking spaces, private beach access, tennis courts, pickle ball courts, large community pool that overlooks Wiggins Pass Waterway, ground level storage area with bathroom and boat docks with Gulf access. This condominium unit represents the pinnacle of Naples living with the beach on one side, the bay on the other and world-famous shopping and dining with close proximity to Waterside Shops, The Mercato and the Naples Philharmonic.brbrFor a video tour of the condominium unit, see: https://youtu.be/oEBzQ0jRW9U.br

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$174.68

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Escape the Cold!

Naples, Florida, United States

Positano Circle is a gated, centrally located desirable community located right off of Livingston Road. It is just minutes to some of the best beaches, shopping and world class dining. This is a beautiful fully furnished 2 Bedroom/2 Bathroom unit with all of the comforts of home. There is a beautiful club house, elevator access to the unit, exercise room and resort like community pool, spa and hot tub. The unit has everything you need to have an amazing stay including High Speed internet, 3 Smart Tv's, Air Conditioner, Ceiling Fans, Dishwasher, Garbage Disposal, Dryer, microwave, Refrigerator with Ice maker, Washer & Dryer. This rental also includes the use of beach chairs, cooler, towels & linens. Walk in closets in each bedroom. Come and escape your everyday and enjoy the Florida sun! We take pride in ownership. We have taken measures to make sure you are comfortable during your stay. A private property manager is available should any issues arise.

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4

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$572.75

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Luxury, High-End Old Naples Retreat | Steps from Fifth Ave and Beach

Naples, Florida, United States

Experience the best of Old Naples at Sun Dial 295 — a stunningly reimagined two-bedroom retreat in one of Naples' most sought-after locations. This residence blends sophisticated design with coastal elegance, offering the perfect balance of luxury and convenience just steps from world-class beaches, dining, and shopping. Step inside to discover a light-filled open-concept layout, featuring a completely redesigned kitchen with a 10-foot island, Miele appliances, and book-matched quartzite countertops. The remastered baths showcase porcelain-clad walls and custom cabinetry, while Legno Bastone wide-plank wood floors flow seamlessly throughout the home. Every detail reflects meticulous craftsmanship and modern comfort — from automated window treatments and smart privacy glass to a cloud ceiling and custom floor-to-ceiling millwork. The elegant home office is perfect for remote work.brbrEnjoy peace of mind with impact windows and doors, a private garage, plus an additional parking space, and personal storage. Lush landscaping surrounds the property, creating a tranquil, private ambiance amid the vibrancy of 5th Avenue. Ideally positioned at the quiet corner of 5th Avenue South and 3rd Street, this home places you mere footsteps from Naples' legendary beaches, upscale boutiques, and the vibrant nightlife of Fifth Ave. This isn't just a residence — it's a refined lifestyle in the heart of Naples' most iconic neighborhood.

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4

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$538.93

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Experience true luxury with this chic and modern condo in Naples.

Naples, Florida, United States

Available December 2025 and January, February, March 2026! Experience the pinnacle of luxury living in Downtown Naples! Ideally located within walking distance to 5th Avenue S. and the beach, this gorgeous turnkey third-floor condo offers 2 bedrooms, 2.5 bathrooms, and garage parking. Tastefully decorated, it features a fantastic split bedroom layout with two king beds, a private open balcony, and in-residence laundry. The kitchen is beautifully designed, with tile flooring throughout and plenty of natural light. Indulge in luxurious amenities like a 3,200 sq ft resort-style pool with beach entry, two lap lanes, chaise lounges, hammock lawns, poolside cabanas and bar, two hot tubs, bocce ball courts, a putting green, grilling areas, fire pits with seating, a game and billiards room, theater, club room, arcade game room, and an amazing fitness center. Enjoy convenient private shuttle service to the beach and downtown Naples in the evenings. HOA approval required and a 30-day minimum.

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$173.49

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Winterpark condo w/resort style pool close to Beach, Restaurants and Shopping.

Naples, Florida, United States

Great Location in Winterpark!!! Minutes from everything!!! brbrSerene and spacious 2/2 (first floor) condo with resort-style pool, tennis/pickleball courts, minutes away from the beach, boat marina, Tin City, Historic Old Naples, 5th Ave Downtown, Restaurant District, and Shopping. brbrFully stocked with all modern day amenities. Just bring your toothbrush, sunglasses, and flip flops to enjoy everything Naples has to offer.

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$197.77

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Lely Greenlinks Resort -White Orchid-Luxury Renovated Modern 1st flr 3bd

Naples, Florida, United States

**Notice of Possible Temporary Pool Closure - Please note that the resort has scheduled a pool equipment replacement project beginning June 22, 2026, which may last for a few weeks. During this time, the shared resort pool amenity may be temporarily closed.brWe wanted to share this information in advance in case pool access is important to your travel plans. Thank you for your understanding, and we apologize for any inconvenience. **brbrThis newly furnished and completely remodeled White Orchid Villa is something we as new owners have worked very hard on to make your vacation destination! With complete renovation, our Villa offers top of the line appliances, cabinets and furniture to provide our guests with a five-star experience. This unit has been refurnished, repainted, new kitchen and bathrooms, kitchen utensils, tables, and was redecorated so our guests have a very enjoyable vacation experience full of great memories!brbrNote: In case if desired dates for your stay are not available in this “White Orchid Villa”, please feel free to check availability on our other “Purple Orchid Villa” (VRBO Property ID#1212380) which is 2 mins away in the closeby building in the same Resort and same level of luxury tasteful upgrades.brbrWe have new modern computer desk, computer chair with lumbar support and printer available for use to our guests.brThis beautiful Lely Resort Villa has it all! With 3 bedrooms (king bed in MBR, queen bed in 1st BDR, 2 twins in 2nd BDR), 2 full bathrooms, a 12 foot by 14-foot den featuring an authentic furniture and comfortable mattresses, the Pack and Play On the Go Playard which Includes Full-Size Bassinet for Infant, the unit is perfect for groups up to 8 people. We have gone out of our way to provide comfort for guests residing in our Villa and can ensure you that beds are comfortable and adults can enjoy and relax on the state-of-the-art sectional sofa. Both bedrooms have walk in brand new revamped bathrooms with new vanities, quartz counters and floor to ceiling tile work, and each bedroom has a closet. The Villa comes with a fully equipped kitchen that underwent complete remodelling with brand new cabinetry, quartz counters, backsplash, etc. The kitchen includes a coffee machine, toaster, blender, appliances, dishwasher, etc. We also provide guests with some complimentary coffee, tea and dry food products to save you a trip to the supermarket upon your initial arrival! We also installed brand new washer and dryer machines in the unit for your use. The Villa is equipped with 4 TV’s (one in each bedroom and one in the living room). There are very many TV HD channels and programs and Netflix included! We also provide complimentary high speed WIFI for our guests! There is an outdoor security camera/audio recording device located outside by the entrance door to the Villa.brbrAs a first floor Villa, it is not only easily accessible to all, but it also has a beautiful furnished, netted lanai facing the ponds in the golf course. In the lanai you may also find some outdoor accessories for your use such as pool noodles, beach chairs, fishing rod, a cooler, tennis equipment, etc. We assure you that this 1550 square foot Villa will provide you with ample room to enjoy your stay and the beautiful Naples. Complimentary 2 free rounds of golf per week of stay from May 15 to October 15.. (Approximate value of $160, Golf cart fee is not included)brbrThis community has plenty of amenities to ensure guests have plenty of activities! These include a heated outdoor pool and spa/hot tub, a clubhouse with a fitness room, tennis courts, poolside BBQ grills, bike paths, bocce ball, 2 renowned golf courses and Sam Snead’s Tavern and Grill. All such amenities are within a couple minute walk from your front door! Walk 2 minutes to be at pool or walk 3 minutes to be at great white tablecloth restaurant/bar/pro-shop. Publix, Fresh Market, fast food, pharmacy, Outback Steakhouse, Carraba's Italian Grill 5 Guy's Burgers, pizza and Chinese food are all within an easy 5-minute, 25 MPH drive while staying inside the Lely Resort. The city of Naples itself is filled with beautiful attractions! The lovely water of the Gulf of Mexico and the extravagant sand beaches are sure to provide you with ultimate relaxation! The city is also perfect for nature lovers with plenty of bike/hike trails and beautiful reserves. Naples &, Marco Island beaches, downtown Naples & beautiful sunsets over the Gulf of Mexico all within a 15-minute drive! The entire Lely development is amazing! Relax and enjoy the weather, blue skies and palm trees!

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Sleeps

$233.1

/ Nightly

Condo

January 1-30, 2027 NOW AVAILABLE! 1BR Olde Naples POOL SPA WD with King Bed

Naples, Florida, United States

This home away from home is at the sought after Castleton Gardens apartments. Amazing Old Naples location of elegant second story (no elevator) one bedroom apartment near the beach. Washer-Dryer in unit. POOL, BBQ and JACUZZI.brbrThis condominium apartment is privately owned and maintained to the highest standards. It is located in Olde Naples in the Downtown area a short walk from famed 5th Ave South with its fantastic restaurants, theater and galleries. Less than 5 minutes walk to Cambier Park with its regular season of events. Tin City and the Naples Dock are nearby, as well as several delightful ice cream parlors. The Naples Zoo is also nearby, along with botanical gardens, and then of course...there are golf courses and the famous white-sand warm water beach.brbrThe local and nearby Farmer’s market is exciting with vendors selling fresh fish, making the best guacamole before your eyes, and exuding the delicious smell of freshly made coffee and pastries. Watching the Neapolitans (yes, that is the proper term for a resident of Naples, Florida), walk their dogs both within the farmer’s market and elsewhere is sport all by itself! This is just a few minutes from this terrific, clean and updated luxury condominium.brbrBoaters can rent boats or personal watercraft or hire fishing guides to take you where the big ones are! You can visit the everglades and see alligators, roseate spoon-bills and other wildlife.brbrThe well-respected Castelton Gardens apartment itself is owned by a professional couple who take pride in their ownership. There is no corporate intermediary when you need to have something attended to; the owners are available just a phone call away. There is not now and never has been smoking in this unit. We have replaced the flooring with elegant wide plank oak flooring. There is a KING-sized bed in the bedroom and there is a beautiful sofa in the living room. (Sorry, no pets are allowed, PER RULES of the condominium!). The apartment is freshly renovated/painted and the building itself is recently painted.brbrThis premiere apartment is on the second floor and renters will appreciate that there is no one above them! The windows have plantation shutters. The central air conditioning and heating work well and there is also a full-apartment humidistat; the refrigerator is stainless steel french door style and there is a microwave and range.brbrYou will appreciate the apartment is fully stocked with pots, pans, utensils, can opener, toaster, teapot, coffee pot, fire extinguisher, overhead fan in the master bedroom and so on!brbrCastleton Gardens, a gated community, has a beautiful heated pool and lounging area with tropical landscaping, chaise lounges and umbrellas. You will have access to a Hot-Tub Spa (JACUZZI) and Bar-B-Que powered by gas! The neighborhood itself is something out of a fairy tale with flowing tropical mature trees, landscaped lawns and manicured shrubs. There is parking provided for one car but there is also parking available on the street outside of the building.brbrOf course, there is TV, Wi-Fi, and internet service. In fact there are two televisions, one in the living room and a smart-tv mounted on the wall of the bedroom. Plus, you will get the top quality service you expect out of a unit like this in a town like this!brbrNaples has the most beautiful white sand beaches and you could bike to the beach if you desired (better to drive!). Several beach towels, beach umbrella and 2 beach chairs are available onsite for your usage. br brCASTLETON GARDENS VACATION CONDOMINIUMbrbrThis property has a 30 day minimum rental period.brbrPOLICIES:br No loud partying or disruptive behaviorbr No Smoking inside the apartment or in courtyardsbr No Petsbr Minimum Age to book: 25br Minimum number of days to book: 30 (thirty)br Refundable damage deposit: $500.00br Cleaning Fee: $150.00br Property Fee to HOA: $150.00br Lost Key: $25.00br br CHECK-IN/CHECK OUT:br 4 pm check inbr 10 am check outbr ********GUEST MUST SIGN LEASE THAT HOST SENDS THEM AND FILL OUT CONDO ASSOCIATION FORM WITHIN A FEW DAYS OF FIRST PAYMENT. ASSOCIATION REQUIRES THE LEASE ALONG WITH THIS FORM...*******************brbrCANCELLATION POLICY:br Non refundable, Non-cancellable. Owner suggests trip cancelation insurance.

1

Bed

1

Bath

2

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$225.58

/ Nightly

Condo

Championship Golf Course, amazing amenities!!

Naples, Florida, United States

Unwind in Naples at this lovely condo. This fabulous property boasts 2 bedrooms, including a cozy king bed and a convenient murphy bed. With 2 bathrooms, complete with a hair dryer and refreshing shower, guests will feel right at home. The welcoming atmosphere extends to the fully equipped kitchen, perfect for preparing delicious meals. Stay connected with WiFi, and take advantage of amenities like a washing machine, heating, AC, and an iron. Plus, there's a fitness room for those looking to stay active. Book now and enjoy everything this amazing condo has to offer.

2

Bed

2

Bath

4

Sleeps

$217.99

/ Nightly

Condo

Stunning Cedar Hammock Condo - Gated -Golf/Resort Amenities 2 Month Minimum

Naples, Florida, United States

Completely Renovated Two bedroom top floor -elevator - with Amazing Views overlooking the pond and golf course at Gated / Guarded Cedar Hammock Golf and Country Club. Available January and February 2026 with 2 month minimum. The interior of this residence has just been completely updated. Your kitchen is fully equipped. Stainless Appliance suite. Quartzite counter tops. New flooring Master bath has large walk in shower. King and Queen Beds. Comfortable and Relaxed Coastal Interior. Great views from this top floor screened veranda. Enjoy golf, swimming, tennis and the Country Club lifestyle. Kitchen is fully equipped. Upscale bed linens. All new TV's. Your $450 resort fees allows for use of the resort style amenities and golf. 20 minutes to beaches and downtown Naples and surrounded by all the conveniences: gas, stores, banks, etc. Easy access to I-75.

2

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2

Bath

4

Sleeps

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