$7,000 Per Month
10317 Heritage Bay Blvd Unit 1416, Naples, FL 34120
Available April 2026 & the 2027 season in Heritage Bay! This beautifully maintained 2 bed, 2 bath first-floor unit offers comfort and convenience—plus a full transferable golf membership for the ultimate resort-style experience. Enjoy your golf membership, stunning amenities, and the best of seasonal living!
Christina Vallozzi Downing Frye Realty Inc.
$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.
$14,000 Per Month
470 Launch Cir Unit 401, Naples, FL 34108
Where luxury meets effortless coastal living. This beautifully updated residence offers approximately 1,700 square feet of open, light-filled living space with a thoughtfully designed 3-bedroom, 2-bath layout—perfect for relaxing and entertaining. Natural light enhances the inviting coastal feel, while upscale finishes throughout include wood flooring, upgraded appliances, new lanai screens and
Lesley Garlock William Raveis Real Estate
$7,000 Per Month
7631 Jacaranda Ln, Naples, FL 34114
Beautiful two bedrooms plus den, two bath attached villa pool home in the amenity rich gated community of Winding Cypress. Main bedroom has a king bed, second bedroom has a queen bed and den has a full size pullout couch that sleeps 2 and includes a full wardrobe armoire for clothing . Spacious attached 2-car garage. Relax on the spacious lanai that overlooks the private pool and peaceful lake
Amber Jasper Grice Realty Inc
$2,400 Per Month
10345 Heritage Bay Blvd Unit 2032, Naples, FL 34120
Annual Rental Furnished Beautifully appointed 2 Bedroom, 2 Bath + Open Den “Brookside” Model featuring an open Great Room floor plan. This elegantly furnished condominium offers new bedroom flooring, tile flooring in main living areas, fresh interior paint, stainless steel appliances, wood cabinetry, and more. Enjoy tranquil lake and golf course views from your private screened lanai. Located in
Linda DeJesus Naples Breeze Realty
$2,975 Per Month
7872 Umberto Ct, Naples, FL 34114
2 BEDROOM PLUS DEN 2 BATHROOM CAPRI. METICULOUS CONDITION, TILE FLOORS THROUGHOUT, 2 CAR GARAGE, HEATED POOL WITH LARGE SCREENED LANAI, PRIVACY GALORE, GATED COMMUNITY, COMMUNITY POOL, LAP POOL, BOCCE, TENNIS COURTS, PICKLE BALL, RESTAURANT, HAIR SALON, TRAVEL AGENCY, ICE CREAM SHOP POST OFFICE, REAL ESTATE OFFICE, GAS STATION
Alexander O'Neill Gulf Coast Properties Group
$5,500 Per Month
9115 Strada Place Unit 5307, Naples, FL 34108
Annual Furnished Property. $5500 per month. Also available monthly throughout the summer and fall. Highly desirable floor plan in the Strada at Mercato! Beautiful open concept living area with wall of impact sliding glass doors bringing in an abundance of natural light. Kitchen has large island perfect for entertaining, Kitchen aid appliances and gas cooking. Spacious flex space that can be used
Joe Hoopfer Premier Sotheby's Int'l Realty
$13,000 Per Month
14614 Stillwater Way, Naples, FL 34114
Beautiful 4 bedroom plus den, 3 1⁄2 Bath, pool home with western lake view. Watch magnificent sunsets from your lanai and living area. White and bright. king in the master and queens in the other three bedrooms. Naples Reserve is chock full of amenities.
Terese DeLuca Berkshire Hathaway FL Realty
$19,500 Per Month
482 Tradewinds Ave, Naples, FL 34108
This beautiful, spacious and comfortable vacation rental home is located in the highly desireable Connors section off of Vanderbilt drive. Veryclose to the beach, Mercato and all that Naples has to offer! 4 bedrooms, 3 full bathrooms, large lanai with a heated pool facing the canal - whatelse could you ask for your winter vacation? Dogs are welcome with owners' approval!
Elina Maranz Naples Vibe Realty, LLC
$25,000 Per Month
144 Gulfport Ct, Marco Island, FL 34145
Introducing this stunning Florida-style home, built in 2023, that embodies the essence of Florida living. Boasting three bedrooms and three full bathrooms, this residence showcases a harmonious blend of modern design and coastal charm. As you enter, you'll immediately notice the large windows that allow an abundance of natural light to fill the home, creating a warm and inviting atmosphere. The
Michel Minella Coldwell Banker Realty
$3,000 Per Month
460 Launch Cir Unit 301, Naples, FL 34108
This impeccably maintained 3BR/2BA condo, with its island-style décor and sunny western exposure, invites you to unwind in comfort. It comes fully furnished with a well-equipped kitchen, luxurious linens, and everything you need for a relaxing tropical escape. Regatta offers resort-style living with a fitness center, poolside grill, picnic area, tropical waterfall pool, spa, lap pool, and boat
Lesley Garlock William Raveis Real Estate
$2,995 Per Month
5286 Nevola Ave, Ave Maria, FL 34142
Like-new stunning 3-bedroom PLUS DEN, 2.5-bathroom two-story home in the highly desirable Ave Maria community is perfect for those seeking a vibrant and active lifestyle. This Hanford model by CC Homes boasts a great room ideal for entertaining, a cozy family room, a den that can serve as a home office or additional guest space, and a loft on the second floor provides flexible living options such
Alma Cue ND Realty
$10,000 Per Month
8502 Palacio Terrace N, Naples, FL 34114
AVAILABLE- APRIL '26 THROUGH NOVEMBER '26. Beautiful 3+Den, 4-bath single-family home in the gated community of "Esplanade at Hacienda Lakes" in South Naples. Nestled on a spacious .19-acre lot, this home offers a blend of indoor charm and outdoor luxury, all with tranquil lake views and coveted Southern exposure. The open-concept living space was perfectly designed for both relaxation and
Taylor Farquhar Coldwell Banker Realty
$12,000 Per Month
8446 Mallards Way, Naples, FL 34114
Welcome to Mallards Landing in Fiddler's Creek in Naples, Florida. This community offers a residential experience complemented by an array of resort-style amenities. Fiddler's Creek is an oasis strategically located between Naples and Marco Island, providing a balance of tranquility and convenient access to local attractions and beaches. This private pool home features a two bed plus den,
Elizabeth Potgieter Premier Sotheby's Int'l Realty
$5,950 Per Month
5555 Double Eagle Cir Unit 3916, Ave Maria, FL 34142
SEASONAL W/FULL GOLF MEMBERSHIP - NOW AVAILABLE FOR FALL 2025 & WINTER 2026 SEASON – BRAND NEW FIRST-FLOOR CONDO WITH FULLY TRANSFERABLE GOLF MEMBERSHIP! Step into effortless luxury and embrace the ultimate golfer’s retreat in this stunning brand-new 2-bedroom, 2-bath terrace condo, perfectly located in the prestigious National Golf & Country Club at Ave Maria. Nestled on the first floor, this
Jennifer Rosenwald William Raveis Real Estate
$5,800 Per Month
172 Plantation Cir, Naples, FL 34104
This beautifully remodeled property has 3bed+den/2bath, and it is fully furnished and equipped with everything you need to feel like you're living in a permanent vacation home. Enjoy a heated pool and hot tub, perfect for relaxation and entertaining. The monthly rental price varies based on the season and the lease duration. Annual Rental Available at $5800. From April to October 2026, the rate
Yasmina Santana Ramirez Marzucco Real Estate
$14,000 Per Month
3443 Gulf Shore Blvd N Unit 309, Naples, FL 34103
Experience the ultimate Naples beachfront lifestyle in this beautifully updated 2-bedroom, 2-bathroom residence at the prestigious Naples Continental Club. Perfectly situated on the 3rd floor, this west-facing unit offers sweeping, unobstructed views of the Gulf of Mexico, ensuring you never miss a spectacular sunset. The heart of the residence is the renovated kitchen, featuring a sleek
Jake Ponsler Naples Vacation Properties
$9,500 Per Month
262 Barefoot Beach Blvd Unit 205, Bonita Springs, FL 34134
Paradise Calling... Just minutes from Barefoot Beach, this 3-bed, 2-bath condo in Barefoot Beach is the ultimate coastal escape. The beautifully updated interior is designed for comfort and relaxation—perfect for a seasonal getaway or extended stay. Spend your days lounging by the beachfront pool, working out in the newly refreshed clubhouse fitness center overlooking the Gulf, or watching the
David Jablonski Compass Florida LLC
$2,800 Per Month
7114 Marconi Ct, Naples, FL 34114
FOUR MONTH MINIMUM STAY. Available June-December '26 and March-December 2027. Turnkey furnished and tastefully renovated 2-bedroom, 2-bath Capri villa offering a lake view, volume ceilings and a bright open layout. Over $100k in updates enhance the home including the renovated kitchen with its soft-close cabinetry, sleek vent hood, under-counter microwave drawer and modern appliances. Additional
Rosie Gouthro Coldwell Banker Realty
$20,000 Per Month
10475 Gulf Shore Dr Unit 161, Naples, FL 34108
** Available for 2027 season ! ** Top Floor • Corner • Gulf-Front • 3 Beds / 2 Baths - Private Beach Access Rarely available top-floor, corner Gulf-front residence in Bayshores of Vanderbilt Beach, offering unobstructed Gulf views, wraparound western and southern exposure, and exceptional privacy. With 1,594 square feet of interior living space, this 3-bedroom, 2-bath residence delivers
Cameron Murray WeichertRealtors-ParadiseHomes
$18,500 Per Month
823 Cassena Rd, Naples, FL 34108
** STUNNING 5 BEDROOM, 5.5 EN SUITE BATH 6,000 SQ FOOT HOME ** AS AN ANNUAL RENTAL ** PINE WOODS ** MOVE IN TODAY ***Luxury Mediterranean Estate for Rent – Naples, FL (Pine Woods / Near Pelican Bay) Welcome to this stunning unfurnished Mediterranean-style two-story estate, ideally located in the highly desirable Pine Woods neighborhood of Naples, just minutes from Pelican Bay. This exceptional
Cheri Anne DeMonico Premier Property Management
$4,500 Per Month
Unlisted Address
AVAILABLE SEASON 2027 with a 3-month minimum. Enjoy SUNSET VIEWS over the Gulf from the patio of this 5th floor 1 bedroom (plus a Murphy Bed) / 1.5 bath condominium located directly across from the beach on Gulf Shore Blvd. in The Moorings. The large community pool and deck over looks Naples Bay and even has a fishing dock! The Primary Bedroom suite features a King-Sized bed and an ensuite bath
Julie Baron Premier Sotheby's Int'l Realty
$30,000 Per Month
271 1st Ave S, Naples, FL 34102
Annual Rate is $22,500 per month. Listed rate is for High Season (Nov.-April). Longer High Season leases have greater discounted rates. Ideally located, this is the quintessential Olde Naples cottage home in a tropical, park-like setting only two and a half blocks to the beach. Cute, charming, and pristine, this three-bedroom home is the perfect Naples escape. Pets welcome! Only a short walk to
Bill Earls John R Wood Properties
$2,749 Per Month
9170 Woodhurst Dr, Naples, FL 34120
ANNUAL UNFURNISHED 3/2 gorgeous custom designed home in the desirable area of North Naples. This is a MUST SEE - Shows better than themodel. Many upgrades throughout - expanded driveway, LED lighting throughout, tile floor, designer paint and wallpaper and more. Bent CreekPreserve is a gated community with fantastic amenities included resort-style swimming pool, spa and fire pit, state of
Elina Maranz Naples Vibe Realty, LLC
$15,000 Per Month
1705 Marsh Run, Naples, FL 34109
Beautiful POOL and SPA home in the highly desirable community of Pelican Marsh! Amazing location, amenities, private pool and a comfortable home - perfect for your winter getaway. 3 bedrooms, 3 bathrooms, a loft, two car garage and a large screened in lanai with a pool and spa. AVAILABLE OFF SEASON 2026 AND SEASON 2027.
Elina Maranz Naples Vibe Realty, LLC
$2,300 Per Month
15191 Cedarwood Ln Unit 2602, Naples, FL 34110
Enjoy stunning sunsets from this sixth-floor unit overlooking the preserve toward the Gulf! This smartly finished and completely furnished 2-bedroom, 2-bath unit features tile floors throughout and a beautifully updated kitchen, complete with granite countertops and stainless steel appliances. The primary suite has a gorgeous view, king bed, luxury walk-in shower, and walk-in closet. Guest room
Marta VanderStarre Realty One Group MVP
$40,000 Per Month
1844 Alamanda Dr, Naples, FL 34102
Nestled in the highly desirable neighborhood of The Moorings, this 5-bedroom, 6-bath home with a den is an ideal winter retreat. The area is renowned for its scenic, tree-lined streets, quiet atmosphere, and proximity to popular shopping, dining, and entertainment, offering a perfect balance of coastal convenience and charm. Upon entering, you’re welcomed into a grand foyer that leads to dual
Sarah Wayne Gulf Coast International Lux R
$9,000 Per Month
1499 Vintage Ln, Naples, FL 34104
Wonderful pool home , newly decorated and furnished, with features that include granite counters in the kitchen and baths, tile throughout, and stainless-steel appliances in the spacious kitchen. The entertainment deck offers a pool with spacious seating areas and an convenient separate grilling area. Updated master ensuite is away from guest rooms for optimal privacy and offers a walk-in closet
Cristina Tutuianu Alfred Robbins Realty Group
$55,000 Per Month
300 2nd Ave N, Naples, FL 34102
BOOKED FROM JAN. 1- April 30, 2026'. This furnished house, designed by MHK Architect, is perfectly situated just 2 blocks to the beach and a short stroll to Fifth Ave. Open floor plan with 370 Sq. Ft. of sliding pocketed doors to maximize the Florida outdoor living experience. With all important southern exposure, the sun lights up the home. Four bedrooms, a huge bonus room, wide wood plank
Marjorie Workinger Royal Shell Real Estate, Inc.
$50,000 Per Month
556 17th Ave S, Naples, FL 34102
Available April - November. Nestled in the prestigious Aqualane Shores neighborhood of Naples, this unique contemporary home offers an unparalleled retreat. Built in 2019, it features 5 bedrooms and 5 bathrooms, with an open floor plan and state-of-the-art finishes. The gourmet kitchen is a chef's dream, complete with a walk-in cedar-lined wine cellar, butler's pantry, double ovens, gas range,
Sarah Wayne Gulf Coast International Lux R
$6,000 Per Month
3435 Laurel Greens Ln S Unit 102, Naples, FL 34119
NOT AVAILABLE FOR JANUARY 2027, FEBRUARY 2027, MARCH 2027, AND APRIL 2027.Welcome to 3435 Laurel Greens Lane South, Unit 102—an elegantly appointed ground-floor carriage home located in the coveted Cypress Woods Golf & Country Club in Naples, Florida. This beautifully furnished vacation rental offers a seamless blend of sophistication and comfort across 1,758 square feet of thoughtfully
Bill Archer Keller Williams Realty Naples
$7,000 Per Month
4664 Abaca Cir, Naples, FL 34119
Beautiful new seasonal 3 BEDROOM+ DEN/ 3 BATHROOM rental available in the highly desirable gated community of Raffia Preserve, perfectly located in prime North Naples. This exceptional home places you just minutes from top conveniences including Founders Square, Pebblebrooke Plaza, premier dining, shopping, grocery stores, and cafés, and is only a 10–15 minute drive to Naples’ world-renowned
Michael Giusto MDM Naples Real Estate LLC
$16,000 Per Month
409 Waterleaf Ct, Marco Island, FL 34145
Welcome to your dream getaway! This stunning 3-bedroom + study, 2-bath waterfront home is the ideal escape for relaxation and entertainment. Designed to embrace the beauty of its natural surroundings, the open-concept living, dining, and kitchen area is bathed in natural light, with floor-to-ceiling sliding glass doors and massive windows that showcase breathtaking expansive water views. Step
Nikki Dimitrova Florida Prime Realty, LLC
$10,000 Per Month
8191 Lucello Terrace S, Naples, FL 34114
Beautifully maintained 4-year-old home available for seasonal or off-season rental in the gated community of Esplanade at Hacienda Lakes in Naples, Florida. This spacious residence features 3 bedrooms plus a den, 3 full bathrooms, and a heated pool. Enjoy resort-style amenities including a clubhouse, fitness center, spa, tennis, bocce, and pickleball courts. Seasonal rate is $9,000 per month plus
Jenny Albaz Real Broker, LLC
$6,000 Per Month
10333 Heritage Bay Blvd Unit 1715, Naples, FL 34120
Available for the 2027 season. Golf membership! Stylish 2 bedroom/2 bath FIRST floor condo with golf course and calming water views in desirable Heritage Bay Golf and Country Club. Fully quipped eat-in kitchen, spacious living area, high tech TVS and internet. Master bedroom has king-size bed. TV and en-suite with large shower. Guest Bedroom has a queen- size bed and TV. Great amenities include
Ann DiLonardo Naples Trust Real Estate Servi
$9,500 Per Month
3837 Ruby Way, Naples, FL 34114
Gorgeous 4 Bed 3 Full bath home for SEASON in Copper Cove Preserve. Pool and gated community in SE Naples. You will love this home with large, screened lanai ready for entertaining with grill, sound bar for music, and lots of seating and dining space overlooking water. The living room has very comfortable leather auto reclining couches. Each bedroom is fresh and ready for your vacation stay. King
Lauren Wells Premier Sotheby's Int'l Realty
$16,500 Per Month
2904 Tiburon Blvd E, Naples, FL 34109
**Experience Luxurious Florida Living in Serafina at Tiburon!** This stunning four-bedroom, 3 full and 2 half-bathroom home in the prestigious Serafina at Tiburon captures the essence of tropical design and the Florida lifestyle. The interior features exquisite wood and stone flooring, complemented by beautiful architectural accents throughout. Guest bedrooms are enhanced with built-in bunk beds,
Gina Nelson Premiere Plus Realty Company
$13,000 Per Month
9584 Caymas Terrace, Naples, FL 34114
Stunning Turnkey Lakefront Home with Pool & Spa – Available for 2026 Season, minimum 30 days. Welcome to this beautifully appointed 3-bedroom, 3 full bath, 2 half bath home featuring a screened-in gas-heated pool and spa with southern exposure and tranquil lake views—the perfect setting for your seasonal escape. Step inside to discover high-end tile flooring throughout, elegant quartz
Eddie Rodriguez John R Wood Properties
$3,300 Per Month
4854 Frattina St, Ave Maria, FL 34142
Picture yourself in this expansive dream home that features the largest single story floor plan in Ave Maria boasting 3,100 sqft under a/c. The residence has 4 bedrooms and 2.5 bathrooms, 3 car garage and sits on one of the largest lakes in Maple Ridge. The home has been freshly painted and the modern traditional decor and design are absolutely gorgeous. As you enter the great room you are
Serafin Sanchez The Keyes Company
$40,000 Per Month
4646 Crayton Rd, Naples, FL 34103
WALK TO THE BEACH from this UPSCALE lakefront, single family home available in PARK SHORE. Enjoy elegant, easy living in this single-story home built in 2020 on nearly 1⁄2 acre with no expense spared! Natural light fills the home with a wide lake view through the 14' wall of sliding glass doors. The Great Room is truly the heart of the home with comfortable seating around the large, mounted Smart
Julie Baron Premier Sotheby's Int'l Realty
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