$3,200
Total Monthly Price
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 and a $250 deposit required.
$54,000 Per Month
740 Banyan Blvd, Naples, FL 34102
Annual rate is $45K per month. FULL SEASONAL RATE SHEET ATTACHED. Longer leases have greater discounted rates. This exceptional estate offers a sophisticated and private retreat in one of Naples’ most desired neighborhoods. Thoughtfully designed with an emphasis on seamless indoor-outdoor living, the property embodies understated elegance and architectural excellence. The expansive great room
Bill Earls John R Wood Properties
$4,500
Total Monthly Price
1120 Little Neck Ct Unit E40, Naples, FL 34102
$49,995 Per Month
1555 Crayton Rd, Naples, FL 34102
Welcome to unparalleled luxury living! This super luxury single-family home, located on prestigious Crayton Road in the sought-after Coquina Sands community, has been newly remodeled with no expense spared. From the over $100k in custom landscaping and lighting to the exceptional finishes throughout, this home offers a lifestyle of elegance and comfort. STEPS TO LOWDERMILK BEACH PARK! Key
Cheri Anne DeMonico Premier Property Management
$4,850 Per Month
985 Sandpiper St, Naples, FL 34102
Annual Rental! 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
$15,000 Per Month
320 Gulf Shore Blvd S, Naples, FL 34102
***DOWNTOWN***OLDE NAPLES***BEACH IS JUST A FEW STEPS FROM FRONT DOOR***4 BEDS/ 3 BATHS***FURNISHED SEASONAL***Stately charm and Olde Naples elegance await you in beautiful Villa Rosa, a classic Bahamian villa just steps from the sugar-sand beaches in Olde Naples. Four bedrooms and three full baths make this home the perfect spot for the whole family to enjoy! There's a large kitchen and living
Angela Muscato Premier Property Management
$9,995 Per Month
404 Broad Ave S, Naples, FL 34102
Amazing location **DOWNTOWN NAPLES**Gorgeous and modern two bedroom two bathroom condo at the Heron Club. Walk to the pier, walk to the beach, walk to 3rd St and 5th Ave! Relax at the pool. Assigned parking spot. Pets are not allowed per HOA. 90 day minimum
$8,000 Per Month
2100 Gulf Shore Blvd N Unit 101, Naples, FL 34102
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. This spacious two-bedroom, two-bath condo features an open-concept living area filled with natural light, a fully equipped
Stacey Cotter John R Wood Properties
$7,500 Per Month
2150 Gulf Shore Blvd N, Naples, FL 34102
Apply online now: Nestled along the picturesque Gulf Shore Boulevard in Naples, Florida, Unit 609 at 2150 Gulf Shore Blvd N offers a serene coastal retreat. This 1,223-square-foot condominium, built in 1968, features two bedrooms and two bathrooms, providing a comfortable and inviting space for residents. The unit's elevated position allows for captivating views of the surrounding area,
$3,150 Per Month
296 4th Ave S Unit 296, Naples, FL 34102
ONE BLOCK FROM NAPLES 5TH AVE S! This 2-story unit is available as an unfurnished annual rental. Located in the heart of Olde Naples, this unit is on the corner of 3rd St South and 4th Ave S just one block north of the shopping & dining mecca of 5th Ave S. It is also just 3 blocks from the beach. Unit has laminate and tile flooring throughout, in unit laundry, a half bath on the first floor with
Kathy Packish ERA Naples Realty Services
$3,700 Per Month
1065 Gulf Shore Blvd N Unit 108, Naples, FL 34102
1065 Gulf Shore Blvd N #108 ~ Ocean Front Naples CondoSHORT-TERM RENTAL | STEPS TO THE BEACH | COMMUNITY POOLAVAILABLE JUNE 8th30 DAY MINIMUM FURNISHEDOcean front condo available for minimum 30 days rentals! Highly desirable Surfside Club with a community pool overlooking the Gulf. Just steps to the powder white Naples sand! This condo offers 2 bedrooms, 2
$28,000 Per Month
223 11th Ave S, Naples, FL 34102
Olde Naples Oasis is a short walk to the beautiful Gulf of Mexico! Nestled in a non-gated coastal neighborhood, this 2-story home with a Key West ambiance is the ideal place to relax & unwind enjoying the Florida sun. Situated right next to Naples 5th Ave AND 3rd Street South where you can find world-famous shopping & dining, plus a 2-block walk or bike ride to the gorgeous beach that lines the
Stacey Cotter John R Wood Properties
$12,000 Per Month
365 5th Ave S, Naples, FL 34102
$2,800 Per Month
940 3rd St S Unit 101, Naples, FL 34102
Absolutely charming residence ideally situated in the heart of Olde Naples on prestigious 3rd Street South. This beautifully updated ground-floor condo features 2 bedrooms and 2 bathrooms, thoughtfully renovated with a modern kitchen and stylish baths. Uniquely, it is the only unit in the community offering a private in-residence washer and dryer, along with flat-screen TVs in both the living
Maria Metzger Royal Shell Real Estate, Inc.
$1,895 Per Month
473 12th Ave S Unit B6, Naples, FL 34102
Beautifully renovated 1BR/1BA first-floor condo just 200 feet from the beach and a short walk to 3rd Street South’s shops and restaurants. This turnkey mid-term rental features a fully updated interior with quartz countertops, stainless steel appliances, modern cabinetry, and stylish finishes throughout. Bright, open living space with luxury flooring and LED fireplace creates a warm, contemporary
$3,500 Per Month
1900 Alamanda Dr Unit 305, Naples, FL 34102
Don’t miss this charming 2-bedroom, 1-bath condo in the centrally located Mimosa Club in Naples. Unit 305 is a top-floor corner unit featuring tile flooring throughout, a functional kitchen, and a private screened balcony with peaceful views. Just minutes from Naples’ beaches, 5th Avenue dining, shopping, and grocery stores. Quiet community with assigned parking. Fast approval process — easy to
Douglas Fernandez SUN REALTY
$6,100 Per Month
1035 3rd Ave S, Naples, FL 34102
NAPLES SQUARE 2/2 condo available annually. Live in luxury, steps from downtown Naples, Gulfshore playhouse, Baker Park, restaurants, shopping and the beach! Enjoy the amenities such as a pool/spa, grilling area, fitness center, and social room. The condo features a large 250 sq ft terrace. Tile flooring throughout. Can be rented partially furnished or unfurnished. Tenants must pass a background
$10,500 Per Month
1200 9th Ave N, Naples, FL 34102
The Bamboo Bungalow is what living in Naples is all about! Located in Lake Park, just a short drive or bike ride to the beach and fifth avenue. This Lake Front house has 3 bedrooms total, one bedroom with a king size bed and den with two Queen size sleeper sofas, and 2 on suite bathrooms. The den can work as a bedroom, office, or another living space. The guest house is fully equipped with a
Tom Puckett Luxury Real Estate LLC
$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
$8,000 Per Month
1550 Gulf Shore Blvd N Unit E5, Naples, FL 34102
Completely renovated in 2025, this coastal modern condo is just a 1 minute walk to the Loudermilk public beach across the street. Watch the dolphins and manatees from your living room or while you lay in bed! Close walk to beach, restaurants and coffee shop. 7 minute drive to 5th Avenue shops and restaurants. New coastal modern furniture and design. Outside of building being painted and updated
Lohra Ballinger Sun Realty
$17,500 Per Month
2203 Gulf Shore Blvd N, Naples, FL 34102
This Indies West condo in the Moorings lives like a home and never had interior damage from hurricanes. Just steps to the white sandy beach and surrounded by water on 3 sides! Newly renovated 2 bed/2 bath condo with an open floor plan, floor to ceiling wall of sliding doors, wood floors, high end cabinets and appliances, tall ceilings, fireplace, and a one-car enclosed garage with extra storage.
$9,000 Per Month
1747 Sandpiper St Unit B, Naples, FL 34102
Beautifully Appointed & Decorated 3 Bedroom, 2 Bath Home. Vaulted Ceiling, New Kitchen, Luxurious Master Bedroom & Bath. Expansive Screened Lanai Overlooking Tranquil Shimmering Lakes, Great For Outdoor Entertaining. Private Gas Grill, Hardwood & Tile Flooring Throughout. 2 Car Attached Garage. Located Royal Arms, Community Features, Heated & Chilled Pool, Tennis & Pickle Ball Courts. EV Charging
Daryl Fiene DC Fiene Realty
$2,400 Per Month
72 7th St S, Naples, FL 34102
Feb & Mar 2027 now available! ALL INCLUSIVE monthly rate May to Dec 19th $3,500. Dec 20th to Apr 2026 $4,550 (rent, tax, cleaning, utilities, cable/wifi, damage waiver all included). Naples FL turnkey short term vacation rental.Everything Olde Naples has to offer at an All Inclusive rate (rent, tax, cleaning, utilities. etc. are all included!). This cozy turnkey 1 bedroom, 1 bath condo
$8,500 Per Month
1351 Curlew Ave Unit 104, Naples, FL 34102
Experience Florida living on the water. This finely furnished 2 bedroom, 2 bath, end unit awaits you, offering a private deck and boat dock overlooking your canal and a front row seat of amazing Naples sunsets, over Naples Bay. Located in a quaint, condominium complex in a highly desirable community, the shops and dining of 5th Avenue of Naples are within a comfortable walking distance. Although
Jessie Morris Marzucco Real Estate
$3,500 Per Month
9229 #103, Naples, FL 34114
Welcome to Fiddler Creek, a stunning upgraded home nestled in the heart of Naples, FL. This property boasts three spacious bedrooms and three full bathrooms, offering ample space for comfort and relaxation. The home is located within a secure gated community, providing an added layer of peace of mind. The modern kitchen is equipped with all stainless steel appliances, perfect for those who love
$11,025 Per Month
101 8th St S Unit 205, Naples, FL 34102
Unit 205 in SoCe Flats is a city-view one bedroom condo offering top of the line luxury finishes! SoCe Flats is an exciting new condominium development in the most desirable neighborhood in Naples, the Paradise Coast's most coveted beach town. "SoCe", named for the ideal location South of Central Avenue in Olde Naples, offers the unique opportunity for a luxurious short-term vacation stay,
Stacey Cotter John R Wood Properties
$4,250 Per Month
1910 Gulf Shore Blvd N Unit 112, Naples, FL 34102
Amazing Gulf Views! Beautifully renovated first floor corner unit in Ambassador Club off Gulf Shore Dr N! Close to 5th AVE. Beach access right across the street. The owners converted the screened in lanai into an atrium area where one can relax and enjoy the beautiful bay views. BONUS: the atrium has slider doors, and screen doors to let fresh air into the home! There is a king bed in the master
Tess Skocik REMAX Affinity Mercato
$15,000 Per Month
1030 3rd Ave S Unit 302, Naples, FL 34102
This beautifully appointed 3-bedroom, 3-bath home places you in the heart of Naples, just moments from premier shopping, dining, and entertainment. The open-concept floor plan offers generous living and dining spaces framed by expansive views, while the sleek kitchen with stainless steel appliances provides an inviting setting for both everyday living and entertaining. A spacious private balcony
Margaret Baumgartner Coldwell Banker Realty
$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
$10,000 Per Month
286 4th St S Unit 203, Naples, FL 34102
All about the prime location!!! You will not find a better deal than this immaculate downtown condo. Nestled in the center of Olde Naples only two blocks from 5th Avenue South and just a short walk or bike ride to the famous white sand beaches of SW Florida. This light and bright corner unit has been meticulously decorated and stocked full of everything you need to enjoy your stay. Two updated
Jake Ponsler Naples Vacation Properties
$14,175 Per Month
101 8th St S Unit 210, Naples, FL 34102
Unit 210 at SoCe Flats is a modern loft designed to impress! The 1-bedroom, 2-bath duplex floor plan has ceiling to floor west facing windows spanning two levels and offers the largest under air square footage in the building. SoCe Flats is an exciting new condominium development in the most desirable neighborhood in Naples, the Paradise Coast's most coveted beach town. "SoCe", named for the
Stacey Cotter John R Wood Properties
$10,000 Per Month
1823 Hurricane Harbor Ln, Naples, FL 34102
Prime, Waterfront, Annual Rental in the heart of Naples now available for $10,000 a month. 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.
Rob Mauceli Compass Florida LLC
$21,000 Per Month
2540 Half Moon Walk, Naples, FL 34102
Available Annually ($21,000/month) and Seasonally ($40,000/month). Nestled in Naples’ most prestigious neighborhood, this stunning Port Royal residence offers the ultimate in coastal luxury—just minutes from the sugar-sand beaches of the Gulf of Mexico and the upscale boutiques and fine dining of iconic Third Street South. Designed with a modern coastal aesthetic, this contemporary home features
Sarah Wayne Gulf Coast International Lux R
$14,000 Per Month
376 3rd St S Unit 102, Naples, FL 34102
Discover the best of Olde Naples living in this beautifully decorated 2-bedroom, 2-bath condo, ideally located just one block from the bustling 5th Ave S. Enjoy easy access to an incredible array of top-rated restaurants, boutique shopping, vibrant nightlife, and charming art galleries — all within walking distance. The pristine white sand beach is only three blocks away, perfect for sunbathing,
Monica Simon William Raveis Real Estate
$3,500 Per Month
401 Bayfront Place Unit 3204, Naples, FL 34102
Welcome to Bayfront in the Heart of Downtown Naples! This exceptionally bright and immaculately kept condo offers everything needed for your Florida lifestyle. Featuring a split two bedroom floor plan, open living space, fully equipped kitchen, separate dining area, and a relaxing oversized courtyard terrace. High-speed internet, WIFI, and plenty of space to work from home. Private, secured,
Roy Head Serhant-Naples
$14,000 Per Month
1125 Central Ave Unit 373, Naples, FL 34102
Available for 2027 Season or off season. Brand new, gorgeous 2BR/2BA + Den third floor condo, professionally decorated and furnished by Rob & Stucky, in the heart of downtown Naples. Both the master suite and the guest bedroom offers king size accommodations. Well equipped kitchen with stainless steel appliances, Quartz counter tops, plenty of room for entertaining. Turnkey furnished with all the
Stephanie Spooner WeichertRealtors-ParadiseHomes
$4,500 Per Month
578 14th St N, Naples, FL 34102
SEASONAL/ANNUAL RENTAL - WATERFRONT COTTAGE WITH GULF ACCESS AND FLOATING DOCK Seasonal: $4,500/moAnnual: $2950/mo unfurnished, $3250/mo furnished. Welcome to Heron's Landing, a recently updated waterfront cottage offering direct Gulf access via the Gordon River and Gordon Pass. Located at the end of a quiet cul-de-sac, this property features a brand-new floating dock perfect for boats, jet
Arturo Sabates Coldwell Banker Realty
$7,000 Per Month
1666 Osprey Ave Unit 203, Naples, FL 34102
Professionally designed with uncompromising quality, this two bedroom two bath condominium is available for off seasonal rental from May 2026 until November 15, 2026 at $3750 per month. January thru April 2027 at $7000 a month. The soothing color palette is reminiscent of the sandy beaches and the sea. Lots of natural light fills the open space. Kitchen features European high gloss cabinets,
Brenda Connolly Buy Coastal Real Estate
$19,000 Per Month
549 7th Ave N, Naples, FL 34102
Welcome to this beautifully updated 3-bedroom residence in the heart of Old Naples, just minutes from pristine white-sand beaches and the renowned shops and dining of 5th Avenue South. Designed for comfort and effortless indoor-outdoor living, the home features an open-concept layout with spacious living areas, modern finishes, and abundant natural light.Step outside to your private backyard
Cliff Glansen Flatfee.com
$25,500 Per Month
1016 7th St S, Naples, FL 34102
Seasonal luxury vacation rental located in Old Naples, Naples, Florida. Exceptional rental property offering an opportunity to stay in one of Naples’ most desirable downtown neighborhoods. Just minutes from the white-sand beaches of the Gulf, this location places you within ideal distance to Old Naples attractions like the 5th Avenue South Art Fair and Cars on 5th Exotic Car Show, and the 3rd
Cynthia Joannou Barefoot Beach Properties
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