Home Vacation Condo Rentals By Owner In Naples, FL

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$620.66

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Regatta Resort, Vanderbilt Beach, Naples, 6 minute walk to beach

Naples, Florida, United States

Regatta is a luxury, gated community located a short walk from Vanderbilt Beach’s white sand and stunning sunsets. This immaculate vacation residence is a fully-furnished three bedroom, 2 bathroom condominium located on the 3rd floor and over-looks the beautiful waterfall and resort pool at the complex. This is an end unit offering plenty of light from the large dining room bay windows and a view to the west of the Ritz Carlton Naples Beach Resort. 1800 sq. ft. of living space, includes a screened-in lanai, which is ideal for morning coffee, dining or relaxing anytime of the day. brbrThe updated kitchen has granite countertops and is fully stocked with everything a cook or family requires. It has free, high-speed Wi-Fi Internet and a brand new washer and dryer in the unit. The master bedroom has a tv, walk-in closet, double sinks and a walk-in shower. The second bedroom has a queen with a tv and the third has two twin beds which share a large bathroom with tub/shower and plenty of towels and linens. The glass-top dining table has six arm chairs and room for additional seating. There are also two barstools at the kitchen counter.brbrDesigned as a resort style community, Regatta is an electronically gated community which offers amazing on-site amenities such as a fitness center, poolside grill and picnic area, gazebo, furnished social room, a zero-entry heated resort salt water pool, hot tub and a lap pool. Parking is on ground level, under building with dual elevators in the lobby. Recycling and luggage carts are in the garage.brbrRegatta is a short two block walk from the award-winning Vanderbilt Beach, which features full size, chair/umbrella rentals, private cabanas, the famous Turtle Club and Buzz’ restaurants, restroom facilities, and a beach store which will open in 2025.brbrWater activities available nearby include parasailing, jet, skiing, boating, and charter fishing. Naples offers several excellent semi-private golf course choices but advanced reservations are highly recommended in season. Whole Foods and Publix grocery are within walking distance. Trader Joe’s, and Walmart are nearby. High end shopping includes the Waterside shops 3 miles, Venetian Village 15 minutes and downtown Naples 8 miles. Only one mile away, is the Mercato development, which offers shopping, multiple dining and nightclub options as well as a Silverspot luxury movie theater. Also, within walking is the Pavilion shopping center which has Mexican, Italian, Irish and American restaurants, plus a movie theatre and Scoops ice cream.brbrElectronic key pad to unit.brbrPets are not allowed.brbr*** All reservations made between January and March must be Saturday to Saturday. Reservations must be made 14 days prior to arrival. A pre-approval Resort Fee of $150.00 is required by Regatta and will emailed to you to fill out and pay Tenant upon signing. brbrbrbrbrbr
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Exceptional(15)

$349.92

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Gulf Front Condo on Beautiful Vanderbilt Beach

Naples, Florida, United States

You can’t stay any closer to the beach than this condo on Vanderbilt Beach. Located between the World-renowned Ritz Carlton and LaPlaya Beach Resorts, enjoy a front row beach accommodation at a fraction of their rates. brEnjoy breathtaking views and the sound of the surf from this sun-drenched 2 bedroom/2 full bath residence that offers western exposure on a very private stretch of Vanderbilt Beach with only 31 units in the building on an oversized lot. The property features secured entry, assigned parking spot, and plenty of guest parking.brInside you will find a master suite with king size bed, including an en-suite bath featuring a walk-in closet, tub, separate shower, and new dual sink vanity. The guest bedroom features two twin beds. Linens are provided.brEnjoy preparing your meals in a fully equipped kitchen featuring all new appliances. Settle into the comfortable lanai to enjoy watching dolphins play as you enjoy your morning coffee or afternoon meal. Watch spectacular sunsets over the Gulf of Mexico each evening.brWhen it’s time for the beach, it’s an easy walk out the back of the building, past the heated pool, and down a short boardwalk to the white sandy beach on the Gulf of Mexico. Beach chairs, towels, and beach umbrellas are provided.brSea Chase is conveniently located in North Naples convenient to shopping, dining, and entertainment venues including Mercato and Waterside Shops. br br--- Please SCROLL DOWN for RATES and AVAILABILITY --br--- CONDO ASSOCIATION requires an EXECUTED LEASE + APPLICATION Please see attachments or contact owner br--- MAX. OCCUPANCY 4 PEOPLE --- NO SMOKING / NO PETS --brRATES ARE BASED ON DOUBLE OCCUPANCY brLODGING TAX: 12%br$150 CONDO PROCESSING/APPLICATION FEEbr$170 DEPARTURE CLEANINGbr$1,000 REFUNDABLE SECURITY DEPOSITbrPAYMENTS: 50% OF TOTAL AMOUNT AT TIME OF RESERVATION - BALANCE SIXTY (60) DAYS PRIOR to LEASE INCEPTON.brPLEASE SEE ATTACHED LEASE AGREEMENT FOR CANCELLATION POLICY
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$116.74

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Tropical Naples Retreat! Pool and Tiki Bar Oasis!

Naples, Florida, United States

Welcome to your Naples beach retreat in beautiful Sterling Oaks— a newly remodeled, freshly painted 2-bedroom, 2-bath condo with a spacious den and sleeper sofa, perfectly located just minutes from Naples’ pristine white-sand beaches, fine dining, and vibrant entertainment.brbrStart your mornings at the coffee bar and enjoy a peaceful cup on the screened lanai surrounded by tropical views. Inside, you’ll find a king suite, a cozy queen guest room, and modern coastal décor designed for both style and comfort.brbrSpend your days lounging by the resort-style pool, sipping drinks at the tiki bar with live weekend music, or exploring nearby attractions like Mercato, 5th Avenue, and Vanderbilt Beach.brbrThis quiet second-floor condo in a secure gated community offers tranquility and convenience in equal measure. Whether you’re looking for a relaxing winter escape or a fun-filled beach getaway, this Naples gem delivers the perfect blend of sunshine, comfort, and coastal charm.brbrHighlightsbrbrCoffee Bar & Morning Lanai Views – Start your day with a fresh brew and sunshine on the screened lanai surrounded by palm trees.brbrSpacious & Comfortable – 2 bedrooms (King & Queen), 2 baths, plus den with sleeper sofa — perfect for guests or family.brbrClose to the Beach – Just minutes to Naples’ white-sand beaches and iconic Gulf sunsets.brbrResort-Style Pool & Tiki Bar – Enjoy live music, tropical cocktails, and a true Florida resort vibe right on site.brbrNewly Remodeled – Freshly painted, modern coastal décor, bright and airy throughout.brbrPrime Location – Near fine dining, shopping, nightlife, Mercato, and Vanderbilt Beach.brbrQuiet 2nd-Floor Unit – Peaceful gated community with lush landscaping and convenient parking.brbrAll the Essentials – Wi-Fi, smart TVs, washer/dryer, and fully equipped kitchen for a comfortable stay.
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Exceptional(1)

$220.09

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Olé Lely, 3 BR, 2.5 Bath, Sleeps 8. Professionally Decorated - New Furniture!

Naples, Florida, United States

IDEAL LOCATION - On Capistrano St S, unit 6402, this condo sits next to the fountains on Rialto Dr., one block from village center. Built in 2007, this was completely furnished brand new in September 2025. It has 3 bedrooms (KING BEDS IN EACH!), 2.5 baths with a pull-out couch with an upgraded queen mattress for a restful nights sleep.brPopular 2-level level floor plan unit with lots of windows and light. This unit is located on the beautiful Ole spine fountains just a block to the Village! The dining room windows overlook the fountains. This is a 3 bedroom 2.5 bath with a 2 car attached garage, is located in the Quad! The Quad features a free-form pool and BBQ area just steps outside your garage door. Ole' Village offers a beautiful tropical pool, 80 seat movie theater, Pub, Ice Cream Parlor, Cafe Bistro, bocce ball, basketball, tennis, sand volleyball & more. brIt has granite throughout kitchen and baths, stainless steel appliances, 70 LED flat screen in the Living room, 50 LED flat screens in all the bedrooms, ceiling fans, 2 car attached garage, 4 bicycles, laundry room, eat in kitchen/dining room, living room. Cozy front porch with a motorized screen to enjoy year round. This Condo also offers exclusive amenities as part of the Quad 2 complex, including a separate pool, outdoor grilling and relaxing sunbeams should you wish for more privacy. The quad is a few steps from the garage. brbrCondo has high speed Wireless Internet and a workspace outside the Master Bedroom with a monitor and a keyboard.brbrCome and experience the Olé lifestyle in Lely Resort, one of the premier communities in Southwest Florida. Lely Resort is an amenity rich community in the heart of Naples. Just minutes from the beautiful beaches and the highly desirable Fifth Avenue Shopping District in downtown Naples. The unit has beach chairs and umbrellas!brbrOle Village Center is one of Lely Resort's newest neighborhoods where a village of Mediterranean styled condos cluster around the village center. The 20,000-square-foot village center amenities include a full-service concierge, bistro, ice cream parlor, English pub, Internet café, coffee shop, business center, library and a 90-seat movie theater. There is also a fitness center with locker rooms and a separate aerobics/dance studio. Outside, the free-form pool includes waterfalls and rock-scapes, and a landscaped sundeck with custom-designed furnishings. A separate pool for small children along with a play area. A beach volley ball court , a bocce ball field, 2 tennis courts, and a full basketball court are there as well.brbrThe library has 6 computers, a fax, printer and copy machine. For golfers, there are 2 championship golf courses on site- the Flamingo Island Golf Course designed by Robert Trent Jones and the Mustang Golf Course by Lee Trevino; these are extremely well maintained and are located right in Lely Resort. You can pay as you play, and the clubhouse has a well-supplied pro shop.brbrA Publix grocery store is conveniently located a mile away as well as several restaurants.brbrNaples Beach and Pier are a 15-20 minute car ride; the Isle of Capri, Marco Island and its beaches are 10-15 minutes away.brbrAlthough very close to the Players Club, this unit does not offer access to this facility as it is a members only establishment with fairly significant annual costs. Many people have asked if membership is included but unfortunately it is not. Ole has all you need right on the property and there are several golf courses nearby that offer fantastic amenities.
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Exceptional(4)

$182.36

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A Sparkling Coastal GEM! - 2 BR/2 BA Condo in Coral Falls/Lely Resort ~

Naples, Florida, United States

Escape to Lely Resort and beautiful Coral Falls for the perfect get away for long or short stays in sunny Naples, Florida! This clean and cozy retreat sparkles with coastal charm, and offers so much in the way of comfort and convenience! Light and bright decor, with easy ground floor access, and just steps to the large Resort-style heated pool with waterfalls, and spa, along with tiki huts and barbecue grills. In the home you'll enjoy a spacious kitchen with all the usual conveniences, and a designer decorated dining area and living room. The adjacent outdoor screened lanai has a view of the nature preserve, teeming with deer and rabbits and exotic birds! The Master Bedroom provides a new King sized bed, with 50 inch Smart TV, an en suite bathroom, and a spacious walk-in closet. The Guest Bedroom is set up with two high-end twin beds, and is served by a second full bath/shower and laundry room with stackable washer and dryer. No stairs, ample free parking, and fully equipped with new bikes, you'll also love the walking trails and sidewalks throughout Lely Resort, as well as nearby pickleball courts. If golfing is your passion, you can enjoy golf at the award-winning public courses designed by Robert Trent Jones and Jack Nicklaus. And a short walk takes you to Publix Supermarket, Home Goods, Burlington Coat Factory, Planet Fitness, Starbucks, Carrabba’s, Millers Ale House, Roadhouse Grill, Chipotle, Pollo Tropical, Outback and so many other dining options and shops. And you're just a 15-minute drive south to Marco Island, which feels like an escape to the Caribbean! Plus, when you drive just 15 minutes to the North and West you'll find the fabulous downtown City of Naples, with five-star dining and high-end shopping, and some of the most stunning beaches on the Gulf Coast of Florida. There are nearby attractions to include fishing, jet ski and boat rentals, sunset boat tours, the Caribbean Gardens Zoo, local, national, and international theater and entertainment, and much, much more! Coral Falls Resort is a quiet community atmosphere with a beautiful pool and spa and friendly and welcoming neighbors. And be sure to check out both Mercado and Fifth Avenue and Third Street offering sophisticated shops, cafes, restaurants, courtyards, and antique fountains set among lush, colorful cascading flowers. Old Town Naples features charming shops and art galleries. The Naples Pier is ideal for watching the sunset over Florida’s famous white sandy beaches. You will feel welcome in one of the most desirable locations in all of Naples! Lely Resort is the most sought-after destination in Naples and is the perfect vacation anytime of the year! Stay for a week, a month, or more! Relax, and enjoy all that beautiful Naples and Marco Island has to offer!
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$249.75

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Newly Remodeled Waterfront Condo on Hurricane Bay — Beach Across the Street

Naples, Florida, United States

Imagine enjoying fabulous sunrises over Hurricane Harbor, in the prestigious southwestern Moorings area of Naples, from our full-sliding-glass-door lanai. Imagine walking just across the street to one of the best beaches in all of Florida. Walk down the beach to the newly built Naples Beach Club and Four Seasons Resort, or to 5th Avenue South and the City Pier in downtown Old Naples -- and invite your friends to truly awesome sunsets over the Gulf of Mexico! This sunny, ground-floor, turnkey-furnished, 1400 sq. ft. end-unit features chiseled-travertine stone flooring; classic crown moulding; thoroughly sound-proofed ceilings; an open floor plan; two LCD HD Smart TVs, an audio system, and WiFi; a dry bar; and remote-controlled shades in the lanai. The all-new kitchen has stainless steel appliances and beautiful granite countertops; contemporary white cabinets and corresponding subway wall tile -- and it's open to the living, dining, and lanai areas. The master bedroom has a premier, new, PranaSleep king-size bed; a large, walk-in closet; an all-new private bath with an upscale all-glass-and-tile shower; and one of the smart TVs. The guest bedroom has two twin beds and a separate, all-new bath with a soaking tub and shower. As a renter in the Ambassador Club, you'll have access to the Club’s beautiful, heated pool; free laundry facilities; gourmet gas grill; rentable boat docks on the bay; parking for your guests; and wonderfully friendly owners and other renters. The dolphins you'll see in the bay (sometimes right at the docks) — and all the shorebirds, such as Great Egrets, Ibises, and Tricolor Herons — are included in the rent. The Unit is available during the time periods shown in the Calendar section of this listing, and a 30-day-minimum stay is required by the Club.
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Exceptional(2)

$182.12

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Greenlinks/Lely - Vibrant coastal flair condo w/office space-Grounds/lake views-Resort Amenities

Naples, Florida, United States

Cleaning and disinfecting of our properties is our highest priority and we are following all CDC guidelines brbr brbrGreenLinks/Lely Resort - Condo next to Flamingo & Mustang Golf Courses & Sam Snead's Tavern - Enjoy lake views from 1st floor private screened lanai! brbr brbrGreenLinks Golf Villas community is located within Lely Resort, which is conveniently situated between Marco Island & Naples downtown 5th Ave. & close to local beaches. This well manicured golf community has unlimited vacation amenities. Vouchers for discounted (peak season) golf rounds (Flamingo & Mustang courses) are provided by the front desk staff October 15 through May 15. Limited free rounds of golf/week (Flamingo & Mustang courses) May 15th through October 15th w/cart fee of $30/round per person. brbr brbr# Bedrooms - 2 brbrPrimary - King w/ensuite bath & direct lanai access brbrGuest - 1 Queen/Full & 1 Twin w/direct access to guest bath brbr brbr# Baths - 2 full brbrPrimary - en suite with dual sinks, soaking tub, separate shower brbrGuest - Shower only brbr brbrThis 2BR/2BA 1st floor unit has lake views from the main living area & primary suite. The private screened lanai, accessible from the Living Room & Primary suite, overlooks the manicured grounds and tranquil lake. brbr brbrThis spacious living room/dining room combo provides ample seating with a large smart TV w/free cable & wifi. brbr brbrThere's also a private designated office space in the foyer for the convenience of working remotely. brbr brbrThe unit boasts a split bedroom floor plan for the ultimate in vacation privacy. The primary bedroom (king bed) provides a TV & direct access to screened lanai. You'll also find a private en suite bath w/dual vanities, hair dryer, garden soaking tub & separate shower. brbr brbrThe guest bedroom (1 queen/full & 1 twin) houses a TV and direct access to the guest/full bath. Guest/full bath has shower only, hair dryer & can be accessed from the hallway or the guest BR via pocket door. brbr brbrThe open & bright kitchen w/granite counter tops and built in microwave is well appointed with cookware and utensils for your culinary endeavors. However, Sam Snead's Tavern is conveniently located within Lely Resort for your dining pleasure as well. Great spot to relax and unwind following a day on one of the two award winning golf courses. brbr brbrStackable washer/dryer housed in closet just off the kitchen. brbr brbrEnjoy lovely grounds and lake views from your 1st floor screened lanai with outdoor dining & conversational seating space. brbr brbrGreenLinks also offers an impressive resort style heated swimming pool & spa with plenty of lounge chair seating & table/chairs for outdoor dining. Gas BBQ grills are located nearby for your outdoor grilling needs. The adjoining clubhouse also provides a fitness center available for tenant use. Additionally, the resort offers tennis, pickleball, bocce ball, shuffleboard & corn hole. brbr brbrThis private rental unit also supplies guests with beach chairs, beach umbrella, beach towels & cooler for use during their stay. brbr brbrGreenLinks is quite simply the obvious solution to your short term (no annual rentals allowed) Naples vacation getaway needs. brbr brbrMonthly Rental Rates are Based on 28 Day Month. brbr brbrCall or go online today to secure your reservation......paradise awaits your arrival!
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Exceptional(1)

$267.29

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Spacious home with enclosed patio & shared outdoor pool

Naples, Florida, United States

Lazy PelicanbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrExperience the perfect blend of comfort, convenience, and coastal charm at this inviting condo located in the vibrant city of Naples, Florida. Ideal for your next vacation escape, this thoughtfully appointed unit offers everything you need for a relaxing and memorable stay. Please note: in order to confirm your reservation, an HOA application must be completed and returned to us within three days of booking.brbrThis dog-friendly retreat features a variety of amenities designed with your comfort in mind. Enjoy leisurely days lounging by the community pool, or unwind on the furnished patio with your morning coffee or evening cocktail. Inside, the cozy living area includes a smart TV and a sofa bed for additional guests, while the dining space offers a welcoming spot to share meals.brbrThe fully equipped kitchen includes modern appliances—refrigerator, stove, oven, dishwasher, blender, toaster, and all the essential cookware—perfect for whipping up vacation meals at your convenience.brbrLocated just a short distance from the pristine waters of the Gulf, this condo is ideal for guests eager to enjoy outdoor adventures such as paddleboarding, snorkeling, fishing, or kayaking. You’ll also find yourself close to top Naples attractions, including water parks, botanical gardens, zoos, museums, and picture-perfect beaches.brbrAfter a day of exploration, return home to relax in the heated pool or stroll to nearby restaurants, cinemas, and shopping centers. Whether you're birdwatching, beachcombing, or simply soaking up the Southwest Florida sun, this charming Naples condo offers the perfect home base for discovering all the beauty and excitement the Gulf Coast has to offer.brbrBook your getaway today and let the Naples lifestyle welcome you!brbrTHINGS TO KNOWbrbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 1 vehicle.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
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$167.58

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3rd-floor snowbird-friendly condo with enclosed balcony, outdoor pool, W/D, AC

Naples, Florida, United States

Bay Forest Condo #2302brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrTreat yourself and your family to a much-deserved escapade at this peaceful third-floor condo only 13 miles away from downtown Naples! Travel Nurses are welcomed ! Right outside your vacation home, you'll find Bay Forest's pristine grounds, which feature more than two miles of paved trails to traverse, a clubhouse, a fitness center, a library, and a sparkling outdoor pool for refreshing swims. Sports enthusiasts will also appreciate the array of activities, which include shuffleboard, pickleball, tennis, and bocce.brbrThis snowbird-friendly retreat boasts a beautifully designated open floor plan with an attached enclosed balcony overlooking the surrounding nature. Spend tranquil evenings unwinding in the living area as you stream your favorite shows and movies on the smart TV, or relax on your private balcony with a refreshing beverage in hand. The kitchen is a chef's playground with all the major appliances and utensils needed to prepare delicious homemade meals for the crew. A laundry room with a washer/dryer allows you to pack as light as you would like. Additional perks include board games and central AC.brbrFind fantastic local attractions nearby, including Tropic Escape Room, Cocohatchee River Park Marina, Delnor-Wiggins Pass State Park, Bonita Beach Park, Hertz Arena, Naples Zoo, and Old Corkscrew Golf Course.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brThis vacation rental requires the completion of an application requiring sensitive information to be submitted directly to the HOA within three days of booking.brbrParking notes: There is free parking available for 1 vehicle.brThis rental is located on floor 3.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
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Exceptional(3)

$202.5

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Ideal NAPLES location for this clean, relaxing condo w/pool and 3 restaurants!

Naples, Florida, United States

This memorable condo is the perfect home base for your trip to Naples! Guests will enjoy a tranquil space featuring one bedroom with a king bed, ideal for a restful night. New, quality linens, fresh paint and professionally cleaned after each stay. The kitchenette and bathroom are clean and convenient, while the excellent climate control keeps the condo comfortable year-round. Whether you’re relaxing indoors or planning your next adventure, this delightful spot offers a cozy retreat at this well-known, ideal location. We think our place will help you experience everything Naples has to offer with so much within walking distance! You'll find 3 famous restaurants on this property like hidden gems of fun and delicious food. Harold's Place is recognized for the 'Best Burgers in Naples'! Vesuvio's Pizza and Bar, and Fujiyama's offers Japanese grill-side steak, and sushi! Gulfcoast Inn is the name of the complex, and we believe our unit 156 is the best one here, not only for it's impeccable condition, but for it's location - a few steps from parking and the beautiful pool, yet private! A beautiful 1 mile walk through exclusive neighborhoods leads you to the endless miles of public beaches on the Gulf. 5th Avenue is a short drive south. We love this place so much and we are honored to be able to share it with you! Enjoy!
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