$17,500 per month
- 3 Beds
- 3 Baths
- 1,500 Sq Ft
- House for Rent
1399 Osprey Ave, Naples, FL 34102
1399 Osprey Ave, Naples, FL 34102$17,500 per month
1399 Osprey Ave, Naples, FL 34102
1399 Osprey Ave, Naples, FL 34102$3,850 per month
1589 Osprey Ave, Naples, FL 34102
1589 Osprey Ave, Naples, FL 34102$7,500 per month
1250 Tuna Ct, Naples, FL 34102
1250 Tuna Ct, Naples, FL 34102$3,750 per month
1100 8th Ave S Unit 230K, Naples, FL 34102
1100 8th Ave S Unit 230K, Naples, FL 34102$4,900 per month
1455 Pelican Ave, Naples, FL 34102
1455 Pelican Ave, Naples, FL 34102$14,500 per month
1455 Pelican Ave, Naples, FL 34102
1455 Pelican Ave, Naples, FL 34102$8,000 per month
1499 3rd St S, Naples, FL 34102
1499 3rd St S, Naples, FL 34102$7,500 per month
1399 Osprey Ave, Naples, FL 34102
1399 Osprey Ave, Naples, FL 34102$6,500 per month
1605 Osprey Ave, Naples, FL 34102
1605 Osprey Ave, Naples, FL 34102$23,000 per month
1499 3rd St S, Naples, FL 34102
1499 3rd St S, Naples, FL 34102$17,500 per month
1605 Osprey Ave, Naples, FL 34102
1605 Osprey Ave, Naples, FL 34102$1,800 - $1,950 per month
Stillwater Cove
2 - 3 Beds
1400 5th Ave N, Naples, FL 34102
$8,000 per month
1004 5th St S Unit 502, Naples, FL 34102
AVAILABLE ANNUALLY or for a longer-term seasonal rental, this charming condominium with 3-bedroom suites and a den is just 4 blocks from the beach and right around the corner from the beautiful shops and restaurants on Third Street. This spacious 2,700 sf condo with a two-car garage features a large great room with two new reclining sofas as well as a table for playing cards or board games; a
Julie Baron Premier Sotheby's Int'l Realty
$5,500 per month
465 8th St N, Naples, FL 34102
Fully furnished home! Available for Annual, Monthly, & Weekly Rentals.AVAILABLE NOW & Beyond! Weekly/Monthly/Yearly Rentals! Call Kate for more info!Be transported back in time to the beachy town days of Olde Naples with the modern comforts of today in this charming newly renovated beach cottage. Located in the heart of Olde Naples, 1 block west of 41, be shopping & dining on 5th
$20,000 per month
1004 5th St S Unit 502, Naples, FL 34102
AVAILABLE as a long-term seasonal rental, this charming condominium with 3-bedroom suites and a den is just 4 blocks from the beach and right around the corner from the beautiful shops and restaurants on Third Street. This spacious 2,700 sf home with a two-car garage features a large great room with two new reclining sofas as well as a table for playing cards or board games; a formal dining area
Julie Baron Premier Sotheby's Int'l Realty
$24,000 per month
150 1st Ave N, Naples, FL 34102
The perfect beach cottage! This classic Olde Naples home has been completely renovated to offer comfort and coastal style in an ideal location along tree-lined 1st Ave N, just three houses from the beach. Walk out your front door to catch nightly sunsets or enjoy early morning beach walks to welcome another beautiful day in paradise. Inside the house, you will find three beautifully appointed
Stacey Cotter John R Wood Properties
$21,500 per month
1080 5th St S, Naples, FL 34102
Fabulous multistory attached villa located right in the heart of Olde Naples! So close to everything this highly desirable neighborhood has to offer. Four stories of luxurious, yet comfortable, accommodations offer the best of Florida living. Numerous luxury appointments include all solid surface flooring throughout, soaring ceilings, granite kitchen countertops, stainless steel appliances plus
Jeffrey Windland Royal Shell Real Estate, Inc.
$25,000 per month
1823 Hurricane Harbor Ln, Naples, FL 34102
Indulge in the epitome of Naples living in this completely renovated waterfront haven. This expansive property boasts a turnkey home, ready for immediate enjoyment, while the 119 feet of seawall beckons for your dream boat. Nestled on a quiet cul-de-sac, this prime location offers unparalleled convenience. Explore the vibrant downtown scene, indulge in retail therapy, or unwind on award-winning
Rob Mauceli Compass Florida LLC
$22,500 per month
600 5th Ave S Unit A-211, Naples, FL 34102
Welcome to the HEART of Olde Naples! Delight in being located smack-dab on Naples’ uber-charming and Historic 5th Ave. South, while simultaneously enjoying a remarkably blissful, quiet, rear (Off-5th) sunny, southern exposure! This 2nd-floor gem touts private, secured, elevator access, generous 2820 ACSF, a 2-story, soaring-ceiling living room showcasing a 20' wall of French doors and windows, a
Marjorie Workinger Royal Shell Real Estate, Inc.
$6,700 per month
766 Central Ave Unit 117, Naples, FL 34102
Three Bedrooms |Two Bathrooms | First -Floor Condo in the Heart of Naples. This beautiful condo offers the perfect blend of comfort and convenience. Ideally located just four blocks from 5th Avenue South Naples' renowed destination for fine dining, shopping, and entertainment and only minutes away from the award winning white sandy beaches on the gulf coast. Enjoy breathtaking sunsets and
Ody Noa Hamro & Associates LLC
$22,000 per month
1165 4th St S Unit 2, Naples, FL 34102
OPEN FOR 2026 Season!! Book EARLY!! OPEN FOR Summer and Fall too! This completely updated 3 bedroom/3+ bath residence offers everything one thinks of in Olde Naples: Central location, Walk to the pristine beaches, Naples' fishing pier, restaurants/shopping. This 2-story Villa sleeps six; it is spacious, well furnished, well equipped, and offers one a very comfortable place to stay in Olde Naples.
Marjorie Workinger Royal Shell Real Estate, Inc.
$33,000 per month
425 5th St S Unit A, Naples, FL 34102
BOOKED FOR THE 2026 SEASON. Location, location, location! This stunning, 3 level, 3 bedroom villa is located less than 1 block from Fifth Avenue in beautiful downtown Naples, featuring a private pool/spa and outdoor kitchen with wet bar & fridge. As you enter the 1st level you are greeted by a spacious foyer leading to a comfortable den with a Murphy bed, large screen TV and private outdoor
Sarah Wayne Gulf Coast International Lux R
$6,500 per month
24 Rivard Rd Unit 12, Naples, FL 34112
Discover the perfect vacation retreat in this newly renovated Naples residence. This inviting home features three bedrooms and two bathrooms, providing comfortable accommodations for guests. The recent renovation includes a third bedroom addition, enhancing the living space and versatility of the property. The interior boasts Italian cabinetry and elegant marble countertops in the kitchen,
Elizabeth Potgieter Premier Sotheby's Int'l Realty
$20,000 per month
1900 Gulf Shore Blvd N Unit 602, Naples, FL 34102
STUNNING, ECLECTIC, first time offered, 6th floor end unit at the Prestigious BOULEVARD CLUB located on Gulf Shore Blvd across the street from Edgewater Beach Hotel. Spacious 3 bedroom 3 ensuite baths, 2100 sq ft, upscale furnishings, but warm and comfortable. Chef's Kitchen with black lacquer Cabinets and Marble Countertops Separate Dining and large great room with cozy den area. Building
Billie Dalesio-Faccinto Downing Frye Realty Inc.
$35,000 per month
860 7th St S, Naples, FL 34102
Quintessential Olde Naples charm. Lovely, updated, pet-friendly, pool home, perfect for a luxurious vacation rentla. The new pool was just poured in early Fall 2020, and the entire outfoor living area is brand new. Owner has recently totally remodeled baths and kitchen area. Walk to 5th, to 3rd, to the beach and to the ASG tennis courts.
Joe Hoopfer Premier Sotheby's Int'l Realty
$15,000 per month
1927 Crayton Rd, Naples, FL 34102
Gorgeous 3/2 Completely remodeled pool home plus 2 car garage with fabulous floor plan. Your beach cottage in the Moorings. New everything, all high-end finishes, wood cabinets, base and crown moldings, solid core doors, quartz counter-tops, new tile, glass tile inlays, high-end fixtures, tray ceilings, recessed lighting, rope lighting, frameless shower doors, commercial-grade hurricane-proof
Carl Suarez Sun Realty
$32,500 per month
477 3rd Ave S Unit 2, Naples, FL 34102
30 Day Minimum. Available November and/or December 2025 at $25,000 per month. Available January or April 2026 at $32,500 per month. Newly Available! Escape to this stunning beach villa in the heart of Olde Naples—just 4 blocks from the Gulf and 2 blocks from the world-class dining, boutique shops, and art galleries of 5th Avenue South. The perfect winter retreat awaits you!The main level
Michael Dedio Naples Trust Real Estate Servi
$14,500 per month
985 Sandpiper St Unit I-204, Naples, FL 34102
Rarely available 3 bedroom end unit located in Naples Bay Resort. Close to shopping, dining and Gulf Beaches. 5 heated pools, lazy river and waterfalls. For adults enjoy the adult only pool, pool bar, cabana rentals with complimentary pool chairs, umbrellas and towels, on-site. Naples Bay Resort is spread over 22 acres offering club facilities which include a spa, gym, three large resort pools, a
Carrie Williamson Collier Home Management
$5,200 per month
1927 Crayton Rd, Naples, FL 34102
Gorgeous 3/2 Completely remodeled pool home plus 2 car garage with fabulous floor plan. Your beach cottage in the Moorings. New everything, all high-end finishes, wood cabinets, base and crown moldings, solid core doors, quartz counter-tops, new tile, glass tile inlays, high-end fixtures, tray ceilings, recessed lighting, rope lighting, frameless shower doors, commercial-grade hurricane-proof
Carl Suarez Sun Realty
$9,000 per month
1140 5th St S Unit A, Naples, FL 34102
Step into the epitome of coastal elegance at 1140 5th Street South, Unit A, located in the heart of Olde Naples, where charm, convenience, and luxury converge. This beautifully appointed vacation rental offers the quintessential Florida lifestyle just a short stroll from the world-renowned 5th Avenue South, Third Street South, fine dining, boutique shopping, and the sugar-white sands of Naples
Bill Archer Keller Williams Realty Naples
$7,500 per month
982 13th St N, Naples, FL 34102
Discover your perfect Naples getaway in the heart of downtown Naples with our brand new, fully renovated seasonal rental in Lake Park. This stunning 3-bedroom, 2.5-bathroom property boasts every aspect of a luxurious home with fantastic natural light throughout. Located just around the corner from the beautiful Naples beaches and the chic dining and shopping of 5th Ave S, this property offers the
Michael Dedio Naples Trust Real Estate Servi
$17,000 per month
650 S Golf Dr, Naples, FL 34102
NOW AVAILABLE FOR JANUARY 2026! THIS HOME IS IN SUCH A GREAT LOCATION AND IS A VERY SHORT WALK TO THE NEW FOUR SEASONS RESORT (FORMERLY THE NAPLES BEACH CLUB) WHICH IS SCHEDULED TO OPEN IN OCTOBER 2025. PRIVATE POOL, LARGE YARD, PLENTY OF PARKING, AND JUST A FEW BLOCKS FROM THE BEAUTIFUL WHITE SAND NAPLES BEACHES. THIS HOME OFFERS THE FEELING OF OLD NAPLES LIVING AND PUTS YOU IN CLOSE PROXIMITY
Gerald Mathusek Downing Frye Realty Inc.
$18,000 per month
850 Central Ave Unit 207, Naples, FL 34102
Experience Coastal Elegance in Downtown Naples! Welcome to Eight Fifty Central, a stunning corner unit condominium in a prime walkable downtown location. This beautifully furnished, single-level home offers a blend of contemporary style and luxurious comfort. The spacious layout features three bedrooms with a king-size bed in the master suite, a queen bed in the guest bedroom, and a versatile
Monica Simon William Raveis Real Estate
$16,000 per month
1400 Gulf Shore Blvd N Unit 310, Naples, FL 34102
Bright and immaculate condo. WALK across the street from this beautiful condo to the fabulous Lowdermilk Beach! Short distance to 5th Ave, Venetian Village and Mercato. Newly and tastefully furnished, including newer; beds, dressers, kitchenware, towels, linens, sofas, dining table w/chairs, light fixtures, outdoor seating, etc. Sit on your balcony and enjoy the view overlooking the Bay. Lounge
Maureen Vita Berkshire Hathaway FL Realty
$40,000 per month
930 9th St S, Naples, FL 34102
9th Street Villa II is a designer furnished luxury townhome that offers access to the ultimate downtown Naples lifestyle. Two light-flooded floors of living area are perched above your private covered outdoor living room and 2-car garage. The outdoor living room is furnished with a dining table that seats 6 as well as a plush sofa and chairs surrounding the outdoor TV and gas fireplace. Adjacent,
Stacey Cotter John R Wood Properties
$12,000 per month
875 6th Ave S Unit 304, Naples, FL 34102
Available for immediate occupancy! The advertised price reflects the off-season rate. This is your opportunity to live within the heart of Olde Naples and reside within one of Southwest Florida's most sought after newer construction luxury downtown condominiums. 875 Sixth Avenue consists of only eight exclusive condominiums within walking distance to all of the great amenities offered within the
David Gruninger William Raveis Real Estate
$55,000 per month
134 16th Ave S, Naples, FL 34102
LD NAPLES home available monthly. Just STEPS from the beach & a quick walk to the 3rd Street shopping/dining district, this completely remodeled (2023) home retains its vintage charm. From the high ceilings and clerestory windows to the sunken living room & detached guest house, you'll appreciate the abundance of natural light, the Old Florida style & its present-day function. The Main House
Julie Baron Premier Sotheby's Int'l Realty
$15,000 per month
675 Yucca Rd, Naples, FL 34102
Experience luxurious coastal living in one of Naples' most sought-after neighborhoods—Coquina Sands. Nestled on an expansive, nearly half-acre corner lot, this beautifully coastal-cottage-style home offers the perfect blend of sophistication and timeless charm. Step inside to over 2,600 square feet of thoughtfully designed living space featuring three spacious bedrooms, each with its own en-suite
Samantha Ford John R Wood Properties
$18,000 per month
1065 Gulf Shore Blvd N Unit 201, Naples, FL 34102
Book your 2025 FALL visit to Naples today! TOES IN THE SAND! FABULOUS OPPORTUNITY TO LEASE A ONE-OF-A-KIND BEACHFRONT CONDO IN THE HIGHLY DESIRABLE COQUINA SANDS AREA OF NAPLES FL AT THE SURFSIDE CLUB! Totally remodeled 3 bedroom, 2.5 bath 2nd floor unit with a fully equipped white kitchen with stainless steel appliances, in-residence laundry room with full size washer and dryer, luxury vinyl
Laurie Bellico William Raveis Real Estate
$14,000 per month
116 3rd St N, Naples, FL 34102
A light, bright and casually inspired beach cottage in the heart of Olde Naples. Close to downtown, beaches and shopping. Primary bedroom features a queen bed, flat-screen TV and ensuite bathroom with marble countertop. 2nd guest room offers another queen bed. flat-screen TV & guest bath. A powder room and a third bedroom offers 1 twin bed and walks onto the large lanai. Home features a
Grace Meholick Premier Sotheby's Int'l Realty
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