$6,000 per month
1111 Central Ave Unit 401, Naples, FL 34102
Experience Naples Living at 1111 Central Avenue in this beautifully furnished and highly appointed condo offering:2 Bedrooms & 2 Bathrooms with 10-foot ceilings and quartz countertops.Southern exposure that bathes the space in natural light.Secure under-building parking.A free executive shuttle service that takes care of the driving for you when you are out on town for
$4,500 per month
1065 Gulf Shore Blvd N Unit 205, Naples, FL 34102
BEACH FRONT condo available for ANNUAL rental. RARE Highly desirable Coquina Sands location between the new Four Seasons Naples Beach Club and the new Olana Naples Residences. If you want to experience the true Naples beach front life style, this is it! Only steps away before your toes touch the sugar white sand and the Crystal Clear Gulf waters. New flooring throughout, new furniture, updated
Carolyn Quistberg Premiere Plus Realty Company
$5,500 per month
473 12th Ave S Unit B-10, Naples, FL 34102
Dates available April 2026 and onward. 30 day minimum. Book early the peak season lease 12 months in advance (2026 peak jan-mar gone). Located in the heart of Naples and just 1 block from the Historic 3rd Street South. You will find fine dining, boutique shops, and a weekly farmer's market. As if that wasn't enough the condo is only a few blocks from the beach and Naples Pier. Bonaire Club
$43,500 per month
255 2nd Ave N, Naples, FL 34102
Discover the ultimate family beach retreat, located just seven doors from the pristine white sands of Old Naples! Perfectly designed for multi-generational gatherings or groups of friends, this unique property features two beautifully updated homes—the main house and a guest house—each offering modern comforts with a touch of historic charm. Recently renovated, both homes are connected by a
Monica Simon William Raveis Real Estate
$2,200 per month
1155 Rosemary Ct Unit Hideaway Naples, Naples, FL 34103
Newly updated beautifully decorated and maintained ground floor two-bedroom, two-bath condo. Walkout screened lanai. Small quiet condo community with community pool. New appliances (kitchen, dishwasher, refrigerator, washer and dryer). New beautiful tile floor, new bathrooms, fully furnished. Naples Hideaway Club is just 1 mile from the beach, and 3 miles from downtown Naples!12
$5,500 per month
642 12th Ave S Unit 642, Naples, FL 34102
Perfectly situated for the quintessential Olde Naples lifestyle, this home places you just 7 blocks from the pristine Gulf beaches, 5 blocks from the cafés, boutiques, and restaurants of 3rd Street, and 3 blocks from The Dock and Bleu Provence—some of the area’s most beloved dining destinations. This beautifully renovated and fully furnished 2-bedroom, first floor home in the desirable 55+
Jane Shawkey Nye John R Wood Properties
$15,000 per month
1111 Central Ave Unit 503, Naples, FL 34102
Eleven Eleven Central amenities include an infinity pool, fitness center, social room, game room, movie theater, grilling area, fire pits, cabana bar with TVs, electric car charging stations, putting green, life-size chess board, Bocce, and many planned social events throughout the season. The private shuttle will take you to the beach or your favorite restaurant. Close to the Zoo, Botanical
$75,000 per month
67 8th Ave S, Naples, FL 34102
Welcome to the Kite House a one of a kind Old Naples family compound only steps to The Gulf of Mexico. This fabulous new Naples Beach Retreat is comprised of three residences sleeping up to 16 people. There are 3 residences comprised of a 3 bedroom, 2 bedroom and one bedroom cottage. The 2 bedroom residence can be rented separately. From the front porches, you are just steps to the sugary sand
Monica Simon William Raveis Real Estate
$2,200 per month
473 12th Ave S Unit B7, Naples, FL 34102
Location, location, locationAvailable for Seasonal or Annual rent!This property is completely renovated. Brand new floors, kitchen and bathroom. Everything is brand new!!!New white interior window shutters for both windows. $2200/month annually$ 4500 November- March $ 5000 January- March 2026. Prime locationProperty is steps
$8,500 per month
1353 Pelican Ave, Naples, FL 34102
** ROYAL HARBOR 2/2 REMODELED TOP TO BOTTON BEAUTY READY FOR SEASON ** BRING YOUR OWN BOAT ** GULF OF MEXICO ACCESS ** BOATING ENTHUSIASTS WITH A BOAT? Well, you've come to the right place here! Welcome to this STUNNING modern completely remodeled 2 bedroom, 2 bathroom home located in the beautiful city of Naples, FL in the Royal Harbor community. This stunning cozy home features a garage for
Cheri Anne DeMonico Premier Property Management
$6,000 per month
1517 Chesapeake Ave Unit 1517 Chesapeake Avenue, Naples, FL 34102
You will relax with this calm & quiet neighborhood sitting on the first floor porch enjoying your 5 o'clock ritual, sometimes seeing the dolphins and an occasional manatee and wave to the boating neighbors as they pass by. We have a boat dock available if your boat is a 22ft. or less, proof of insurance required.
$2,950 per month
216 Banyan Blvd, Naples, FL 34102
NAPLES CALUSA CLUB CONDO OFFERS CONDO FOR ANNUAL RENT IN 2026Steps to the beach. Just across the street to Lowdermilk Park. Courtyard pool at the building, elevator or steps to the second floor of this very nice two bedroom two bath, carpeted, screened balcony facing NW. Convenient to downtown Olde Naples, the new Four Seasons Hotel under construction, five minutes to fresh market and shopping
Karen Wagenheim Downing Frye Realty Inc.
$2,200 per month
53 High Point Cir W Unit 112, Naples, FL 34103
High Point CC 2/2 first floor corner unit, unfurnished available for rentMonthly rent $2,200.00 Beautiful first floor, corner unit one mile to the Beach, tile floors, stainless steel appliances, master bedroom walk-in closet, in unit full size washer and dryer, totally move-in ready.Rent includes:Cable TV, Wi-Fi internet, water, Executive Golf Curse, no extra charge for
$6,000 per month
1400 Blue Point Ave Unit 208, Naples, FL 34102
Escape to paradise at Escondido Marina Condos in Naples, FL—your perfect seasonal retreat just minutes from pristine beaches, world-class dining, and the charm of 5th Avenue and 3rd Street South. This beautifully furnished condo offers a bright, spacious layout with a fully equipped kitchen, inviting living spaces, and a private lanai overlooking the canal. The community features a heated pool
Max Marvelle John R Wood Properties
$2,000 per month
685 12th Ave S Unit Everglades, Naples, FL 34102
FURNISHED AND TURN-KEY! Downtown Olde Naples Annual Rental/Possibly for season. $2000 annual/$4500 seasonal. Walk to Third St. S. Avail now. No pets. 55 and older. if seasonal, the dates would go from January 1 to the end of April all payable in advance plus security deposit.Tenants would have access to Village Green pool and clubhouse, which is also located on 12th Ave S. and features:
$15,000 per month
1125 Central Ave Unit 469, Naples, FL 34102
Offered turnkey furnished this stylish 2 Bedroom + Den fourth-floor residence at Eleven Eleven Central places you at the center of Naples’ most exciting live-work-play district. Designed with a clean-modern aesthetic, the home welcomes you with an open and airy layout, thoughtfully curated furnishings, and a great room that flows out to a private balcony overlooking the privately landscaped
Kaleena Figaro Compass Florida LLC
$7,000 per month
2261 11th St N, Naples, FL 34103
Location, location, location!!!! This furnished 4 bedroom/2 bath home is close to everything both the City & Olde Naples have to offer including schools, the beach, Coastland Center Mall and chic 5th Avenue South shopping and dining district offering fine shopping, dining and entertainment. Queen bed in the master with a second queen in the 1st guest bedroom, the 2nd guest bedroom offers 2 twins
Maria Metzger Royal Shell Real Estate, Inc.
$24,000 per month
201 8th St S Unit 209, Naples, FL 34102
Indulge in the ultimate luxury and convenience at The Mark on 8th, a premier condominium community in the heart of Olde Naples. Just steps from world-class boutiques, charming cafés, acclaimed restaurants, and the pristine sandy beaches of the Gulf of Mexico, this prime location offers everything you need for an unforgettable Southwest Florida vacation. Unit 209 is thoughtfully designed to
Stacey Cotter John R Wood Properties
$9,000 per month
284 4th St S Unit 103, Naples, FL 34102
The envy of location! Tucked into the heart of Olde Naples just two blocks from 5th Ave S and four blocks from the sugar white sand beach, Beach Breeze offers the opportunity to live in one of the most desirable residential neighborhoods in the USA. Unit 284 offers the convenience of a ground floor entry and has wonderful views out to tree-lined 4th St S from newer impact resistant windows.
Stacey Cotter John R Wood Properties
$6,500 per month
980 7th Ave S Unit 204, Naples, FL 34102
Welcome to Castleton Gardens 204, a newly renovated and beautifully furnished condo perfectly situated in the heart of Olde Naples. Designed in a breezy coastal contemporary style, this charming retreat is ideal for a couple or solo traveler seeking comfort and style. This inviting condo offers a spacious bedroom with a plush king-sized bed, an updated bathroom with designer touches, a fully
Stacey Cotter John R Wood Properties
$20,000 per month
993 8th St S Unit 2, Naples, FL 34102
January is offered at $18,000 January - April 20,000 per month. Situated in the heart of Olde Naples, this elegant four-bedroom, five-bath townhouse delivers the perfect blend of luxury, comfort, and walkable convenience. Nestled between 5th Avenue South and Third Street South, you’ll be just moments from world-class dining, boutique shopping, and Naples’ iconic white-sand beaches.
Jake Ponsler Naples Vacation Properties
$42,900 per month
47 8th Ave S, Naples, FL 34102
Plan Your Beach Vacation Now! Welcome to the “Kite House,” a charming Old Naples retreat just steps from the Gulf of Mexico. This listing features the beautifully designed 2-bedroom, 2-bath residence, perfect for a family getaway or a relaxing couples’ retreat. Enjoy all the comforts of a newly remodeled property, complete with exquisite décor, thoughtful design, and state-of-the-art appliances.,
Monica Simon William Raveis Real Estate
$5,000 per month
780 10th Ave S Unit 22, Naples, FL 34102
Discover the ultimate vacation retreat in this charming 1-bedroom, 1-bathroom corner-unit condo, perfectly nestled in the highly sought-after Twin Palms complex. Located on the second floor, this beachy oasis offers privacy and tranquility just a short stroll from the white-sand beaches of Naples and the Gulf of Mexico. It’s also steps away from the vibrant dining, shopping, and entertainment of
Monica Simon William Raveis Real Estate
$5,500 per month
1300 Gulf Shore Blvd N Unit 407, Naples, FL 34102
Escape to paradise in this beautifully updated 2-bedroom, 2-bath vacation rental, ideally located on Gulf Shore Boulevard N in Naples’ coveted Coquina Sands neighborhood. JUST STEPS from the soft sands of Lowdermilk Park Beach, this fourth-floor end unit offers an inviting coastal retreat with modern amenities and an unbeatable location. Inside, you’ll find a bright, welcoming space with tile
Monica Simon William Raveis Real Estate
$14,000 per month
1530 5th Ave S Unit C-311, Naples, FL 34102
This 3BR, 3 BA condo at the amenities rich, Naples Bay Resort could be your perfect retreat. Located in the heart of Naples, Naples Bay Resort is walking distance to iconic 5th Avenue and 3rd Street South with gorgeous views of Naples Bay Marina. Enjoy preparing your meals in the contemporary kitchen with Wolf appliances, granite countertops, and breakfast bar. The dining room table seats 8 and
Sarah Wayne Gulf Coast International Lux R
$6,500 per month
1100 Little Neck Ct Unit F53, Naples, FL 34102
Live the Naples lifestyle at Four Winds! This 2/2 condo is located right on Naples Bay just minutes from 5th Ave and downtown. The screened balcony offers views of the canal and bay and the unit comes with access to your own private dock should you choose to bring or rent a boat. Each bedroom and the living room has a flat screen TV and the kitchen is fully equipped. The unit is on the first
Stacey Cotter John R Wood Properties
$2,250 per month
1751 Smugglers Cove Unit B, Naples, FL 34112
100% renovated, new floors, new doors, new kitchen and new bathroom!! The back half of this duplex is like brand new with all new appliances,everything has been replaced. Very spacious 2 bedroom 1 bath with screened in porch area. Brand new washer and dryer as well. This unit islocated within biking distance to both 5th Avenue downtown Naples and local beaches.
Tony Dedio Naples Trust Real Estate Servi
$30,000 per month
201 8th St S Unit 311, Naples, FL 34102
Indulge in the pinnacle of luxury and convenience at The Mark on 8th, a premier condominium development nestled in the heart of Olde Naples. Just a short walk from boutiques, quaint cafés, acclaimed restaurants, and the pristine beaches along the Gulf of Mexico, this exceptional location is ideal for a Southwest Florida getaway. Unit 311 is meticulously designed to accommodate larger groups. The
Stacey Cotter John R Wood Properties
$9,000 per month
1910 Gulf Shore Blvd N Unit 208, Naples, FL 34102
Panoramic Bay View! This exquisitely updated second-floor, two-bedroom, two-bath condominium in the Ambassador Club at The Moorings boasts floor-to-ceiling windows framing breathtaking views of Hurricane Harbor. Designed with modern elegance, it features sleek wood-look tile floors, quartzite countertops, and a sophisticated kitchen with stainless steel appliances and a stylish breakfast bar.
Maria Metzger Royal Shell Real Estate, Inc.
$30,000 per month
12 6th St S, Naples, FL 34102
Rented for Season 2026. Welcome to Naples Coastal Retreat – Your Luxurious Getaway! Experience the epitome of coastal contemporary living at our stunning vacation rental home in beautiful Naples, FL. This exquisite three-bedroom sanctuary, each with its own attached bathroom, offers the perfect blend of luxury, comfort, and style, making it an ideal retreat for families or groups of friends. Each
Michael Dedio Naples Trust Real Estate Servi
$18,500 per month
2211 Gulf Shore Blvd N Unit C4, Naples, FL 34102
NEW VACATION RENTAL – Stunning 2nd-floor beachfront villa in the exclusive Indies West, located on the point of Doctor’s Pass and just steps from what feels like your own private beach. Enjoy breathtaking views and vibrant sunsets from your private screened lanai, while watching dolphins and manatees play. This beautifully updated villa features a new kitchen with quartz countertops and
Ryan Buchalter William Raveis Real Estate
$11,000 per month
1977 Gulf Shore Blvd N Unit 205, Naples, FL 34102
A Spectacular Waterfront condo offered as an in-season rental at Gulf Towers just steps away from the beach and equipped with a pool for relaxation is just the start. Enjoy breath taking views from every window! Entertain guests in the lobby equipped with a recently renovated kitchen, fireplace and sofas with TV or privately in the luxurious kitchen at home. Plenty of storage, parking room for 1
Paul Knott Worldview Properties, LLC
$5,000 per month
780 10th Ave S Unit 1, Naples, FL 34102
Located in the heart of Olde Naples sits this modern updated yet cozy first floor corner unit in a peaceful boutique building that is reminiscent of the Olde Naples we all love! With just 12 units in Twin Palms, it offers a quiet retreat after fun filled days at the white-sandy beaches. Enjoy the serenity of the peaceful community courtyard which is a favor of all who stay at Twin Palms. This
Teresa Koch Downing Frye Realty Inc.
$35,000 per month
1645 Mullet Ct, Naples, FL 34102
Beautiful upgrade home located on a small culdesac in Royal Harbor. Enjoy dolphins in your backyard canal while floating in the large pool or sipping your coffee in the morning. Owners have an eye for detail and you will find this home to be everything you are looking for during your stay in Naples. Pet friendly and a Captain for hire to enjoy boat rides for sunset and sightseeing.
Jason Minder Bayview Realty of Florida
$14,500 per month
1030 3rd Ave S Unit 504, Naples, FL 34102
SEASONAL RENTAL – DOWNTOWN NAPLES! Beautifully furnished 2BR + Den residence in a premier Old Naples location within walking distance to 5th Avenue South, 3rd Street South, world-class dining, boutique shopping, galleries, and the pristine Gulf beaches. This light and bright unit features an open floor plan, high ceilings, designer finishes, and a private balcony ideal for enjoying the Naples
Nathan Dyer William Raveis Real Estate
$11,000 per month
1977 Gulf Shore Blvd N Unit 401, Naples, FL 34102
Experience effortless coastal living in this beautifully appointed fourth-floor residence at Gulf Towers, perfectly positioned along the pristine shores of the Moorings. This two-bedroom, two-bath condominium spans approximately 1,300 square feet and showcases a timeless blend of comfort, style, and an unbeatable Gulf-front setting. Wake up to the rhythm of the waves and end each day with the
Calley Fletcher Downing Frye Realty Inc.
$7,500 per month
1950 Gulf Shore Blvd N Unit 101, Naples, FL 34102
Spectacular large 2 bedroom 2 Bathroom with den/3rd Bedroom located at Palm Bay Villas! Just steps away from the Moorings Private Beach Club, tenant can join the beach club with paid fee. This newly remodeled coastal style seasonal rental is ready for the season, available Jan, Feb, Mar 2026 & 2027, unit has never been rented. Impeccably furnished and turn key ready! Buildings amenities consist
Rafael Leon Douglas Elliman Florida,LLC
$7,500 per month
1950 Gulf Shore Blvd N Unit 108, Naples, FL 34102
Spectacular large 2 bedroom 2 Bathroom with den/3rd Bedroom located at Palm Bay Villas! Just steps away from the Moorings Private Beach Club, tenant can join the beach club with paid fee. This newly remodeled coastal style seasonal rental is ready for the season, available Jan, Feb, Mar 2026 & 2027, unit has never been rented. Impeccably furnished and turn key ready! Buildings amenities consist
Rafael Leon Douglas Elliman Florida,LLC
$22,000 per month
370 6th Ave S, Naples, FL 34102
NOW AVAILABLE FOR JANUARY 2026 at $25,000 plus taxes and fees due to cancelation. Nestled in the heart of Olde Naples, this exquisite 4-bedroom, 3-bathroom home offers the perfect blend of luxury, privacy, and convenience. With its prime location just one block from the bustling 5th Avenue and three blocks from the pristine beaches, you'll have the best of both worlds: the tranquility of a
Michael Dedio Naples Trust Real Estate Servi
$32,500 per month
258 9th Ave S, Naples, FL 34102
NEW VACATION RENTAL - Available for 2026 season. Perfectly situated between 5th Avenue South and 3rd Street South, this Olde Naples residence offers an unbeatable walkable lifestyle—just steps to the sandy white beaches and surrounded by world-class dining, boutique shopping, and daily entertainment. Enjoy morning coffee on 5th, dinner on 3rd, and sunsets on the Gulf without ever needing a car.
Tina Keppy William Raveis Real Estate
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