Naples, FL Homes for Rent with Private Pool

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  $9,800 Per Month

  • 4 Beds
  • 3 Baths
  • 2,894 Sq Ft
  • House for Rent

  1973 Yellowfin Cir, Naples, FL 34114

  Available for January and April 2026. Welcome to this gorgeous new single-family home in Manatee Cove, featuring new furnishings and a stunning water view. Embrace every moment and enjoy this large pool, spa, and lanai, as well as an outdoor kitchen equipped with a built-in style gas grill, an extra-burner grill, loungers, a table for 6, and a couch/chairs for outdoor entertaining. The first

  Aniledif Ayala Burger Premier Sotheby's Int'l Realty

  1973 Yellowfin Cir, Naples, FL 34114
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  $43,500 Per Month

  • 4 Beds
  • 4 Baths
  • 2,700 Sq Ft
  • House for Rent

  369 2nd Ave N, Naples, FL 34102

  Listed rate is for High Season (November-April). Longer High Season leases have greater discounted rates. Annual Rate is $32,625 / month. Located just three blocks from the Gulf, this charming residence offers the perfect blend of elegance, comfort, and coastal living. Nestled on the property is a sun-drenched main residence featuring open-concept interiors with vaulted ceilings and a cozy

  Bill Earls John R Wood Properties

  369 2nd Ave N, Naples, FL 34102
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  $100,000 Per Month

  • 5 Beds
  • 10 Baths
  • 5,256 Sq Ft
  • House for Rent

  637 Palm Cir W, Naples, FL 34102

  Stunning New Construction home being completed. Enjoy lots of light, a huge kitchen, and plenty of outdoor space. The home boasts five bedrooms, one office/study, and additional fitness room. The exterior features a pool, spa, and cold plunge, along with fire pit and bocce ball court. There is a lanai with covered and uncovered seating as well as a large balcony and lanai upstairs with a

  Stephanie Harrison Downing Frye Realty Inc.

  637 Palm Cir W, Naples, FL 34102
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  $58,500 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,229 Sq Ft
  • House for Rent

  380 5th Ave N, Naples, FL 34102

  Experience life in one of Naples' most pleasant neighborhoods just steps to the beach! Southern Sunset is a newly renovated and designer decorated coastal style home with all of the features and amenities you're searching for. Enter from the circular drive into an open living room with views out to the southern exposure lanai, heated pool and hot tub. A new picture window screen enclosure

  Stacey Cotter John R Wood Properties

  380 5th Ave N, Naples, FL 34102
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  $3,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,983 Sq Ft
  • House for Rent

  7710 Tommasi Ct, Naples, FL 34114

  Bright & Spacious Home in Verona Walk!Welcome to this beautiful 3-bedroom + den home in the sought-after gated community of Verona Walk! Filled with natural light, this residence offers a warm, inviting atmosphere and a perfect balance of comfort and style.The open-concept living area flows seamlessly into the kitchen, making it ideal for both relaxing at home and entertaining guests.

  Maureen Vita Berkshire Hathaway FL Realty

  7710 Tommasi Ct, Naples, FL 34114
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  $3,950 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,427 Sq Ft
  • House for Rent

  4007 Pegasus Way, Naples, FL 34120

  Welcome to Skysail—your resort-style lakefront retreat with wide-water views. This upgraded Sea Mist model in the COVE home area, Lot lines are wider, offers 3 bedrooms + a den with glass French doors, 2.5 baths, and an open great room plan with coffered ceilings. Coastal exterior elevation with impact-resistant windows/doors for storm-ready peace of mind. Bright, modern interior with light

  Susan Procacci Florida Home Realty, Inc.

  4007 Pegasus Way, Naples, FL 34120
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  $2,999 Per Month

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • House for Rent

  6 Hawk St, Naples, FL 34113

  Great Location, All tile, 3 Bedrooms, 2 Full Bathrooms. In ground Pool.Second house to the Bay.

  Kent Kajy RE Florida Homes

  6 Hawk St, Naples, FL 34113
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  $8,000 Per Month

  • 4 Beds
  • 2 Baths
  • 1,921 Sq Ft
  • House for Rent

  333 5th St SW, Naples, FL 34117

  Enjoy the peaceful of the nature, enjoying with your family and friends this beautiful house, features pool and spa,

  Maria Rocio Mora DomainRealty.com LLC

  333 5th St SW, Naples, FL 34117
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  $11,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,805 Sq Ft
  • House for Rent

  7567 Winding Cypress Dr, Naples, FL 34114

  From the moment you arrive at the stunning entry, Winding Cypress invites you into this wonderful community. This natural gas, resort-style community, remaining almost 2/3 preserve, welcomes you with a streetscape of superb views and new homes designed for the way you live. This premier Naples location offers highly attractive fees for the variety of world-class amenities right in your own

  Dave Garafola Reed Property Mgt. & Sales

  7567 Winding Cypress Dr, Naples, FL 34114
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  $3,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,540 Sq Ft
  • Apartment for Rent

  4194 Saint George Ln, Naples, FL 34119

  Tropical getaway available May through December. Bright and Airy Island Walk beauty featuring 2 bed + den, 2 full baths with private heated pool, 2 car garage in this highly desired, amenity rich, gated community. Tastefully furnished and decorated, plantation shutters, 1 King bed, 2 Queen beds, cable TV, high speed internet & more this property is ready for your comfort and relaxation. Come and

  Louis Schiavo Realty One Group MVP

  4194 Saint George Ln, Naples, FL 34119
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  $5,250 Per Month

  • 4 Beds
  • 3 Baths
  • 2,402 Sq Ft
  • House for Rent

  10842 Vanderbilt Dr, Naples, FL 34108

  Annual rental, offered furnished or unfurnished. Welcome to our luxurious home nestled in the heart of Naples Park, where every detail has been carefully curated to provide the ultimate getaway experience. This exquisite property boasts 4 bedrooms and 3 bathrooms. As you step inside, you'll be greeted by a spacious and elegantly furnished living area, perfect for unwinding after a day of

  Michael Dedio Naples Trust Real Estate Servi

  10842 Vanderbilt Dr, Naples, FL 34108
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  $7,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,807 Sq Ft
  • House for Rent

  333 Wentworth Ct, Naples, FL 34104

  CHARMING 3-BEDROOM, 2 BATHROOM SINGLE FAMILY HOME WITH PRIVATE SOLAR-HEATED POOL IN BERKSHIRE LAKES READY FOR A SEASONAL TENANT ** Welcome to this beautifully maintained 3-bedroom, 2-bathroom single-family home in the desirable Berkshire Lakes community. With 1,807 square feet of living space, this home offers the perfect blend of comfort, style, and convenience, ideal for entertaining or

  Cheri Anne DeMonico Premier Property Management

  333 Wentworth Ct, Naples, FL 34104
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  $6,800 Per Month

  • 3 Beds
  • 3 Baths
  • 2,366 Sq Ft
  • House for Rent

  9552 Caymas Terrace, Naples, FL 34114

  Experience the ultimate in style and comfort with this beautifully designed luxury residence located in Caymas, one of Naples’ most desirable new communities. This recently built 3-bedroom plus den, 3-bathroom home offers over 2,400 sq. ft. of living space and showcases the sought-after Brixton model, enhanced with high-end finishes and thoughtful upgrades throughout. Every detail has been

  Eddie Rodriguez John R Wood Properties

  9552 Caymas Terrace, Naples, FL 34114
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  $7,500 Per Month

  • 3 Beds
  • 2 Baths
  • 2,385 Sq Ft
  • House for Rent

  3951 Ruxton Rd, Naples, FL 34116

  RARELY AVAILABLE TO RENT. Come see this beautiful 3-bedroom plus den, 2 Bath home in Forest Park, where all the work has been done for you. The split-bedroom layout is perfect for family life or hosting guests, giving everyone their own space. The bright, eat-in kitchen is a natural gathering spot, fully equipped with stainless steel appliances, granite countertops, custom cabinets, and a large

  David Roy Downing Frye Realty Inc.

  3951 Ruxton Rd, Naples, FL 34116
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  $20,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,406 Sq Ft
  • House for Rent

  8795 Calypso Ct, Naples, FL 34112

  NOT AVAILABLE FOR FEBRUARY 2027 AND MARCH 2027.Discover unparalleled luxury featuring the newly available, exquisite 2023 Wisteria floor plan with a preferred WESTERLY VIEW FOR FANTASTIC SUNSETS. This impressive property spans 3100 sq ft of indoor-outdoor living space, offering 3 beautifully decorated bedrooms, 3 total bathrooms including the master with its en-suite bath, and a private den

  Bill Archer Keller Williams Realty Naples

  8795 Calypso Ct, Naples, FL 34112
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  $10,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,905 Sq Ft
  • House for Rent

  1466 Vintage Ln, Naples, FL 34104

  Superb Naples Estate in Lakefront Luxury *** HEART of Naples *** Discover this impeccably renovated and professionally designed furnished 3-bedroom, 2-bathroom pool home tucked away on a quiet cul-de-sac in the prestigious gated community of Briarwood. This serene retreat perfectly blends sophistication and comfort—just 10 minutes from Naples’ white-sand beaches, world-class dining on 5th Avenue,

  Christopher Bozek Avanti Way Realty LLC

  1466 Vintage Ln, Naples, FL 34104
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  $9,995 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,900 Sq Ft
  • House for Rent

  5815 Persimmon Way, Naples, FL 34110

  One of Naples' most desirable gated communities! Bright western exposure and serene vista golf course views from this two story detached villa residence. Furnished in a casual Florida style decor scheme of neutral tones with accents of color throughout. Main living level comprises of the main living room, dining room, kitchen, master suite, full office and powder room. The second level boasts a

  Jeffrey Windland Royal Shell Real Estate, Inc.

  5815 Persimmon Way, Naples, FL 34110
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  $9,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,871 Sq Ft
  • House for Rent

  18127 Royal Hammock Blvd, Naples, FL 34114

  ***NOW AVAILABLE FOR 2027 SEASON*** This gorgeous 3 bedroom plus den, 2 bath home in the highly desirable Royal Palm Golf Estates is the perfect Naples getaway. Situated on nearly half an acre of lush landscaping, the property offers the ultimate in privacy and peaceful estate-style living. The open floor plan features a cozy living room with beautiful tile floors and a large entertainment

  Sarah Wayne Gulf Coast International Lux R

  18127 Royal Hammock Blvd, Naples, FL 34114
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  $5,250 Per Month

  • 4 Beds
  • 2 Baths
  • 2,362 Sq Ft
  • House for Rent

  14265 Manchester Dr, Naples, FL 34114

  Furnished Annual Rental - Welcome to this beautifully maintained 4-bedroom home located in the gated community of Reflection Lakes in Naples. Offering over 2,000 square feet of living space, this residence features an impressive double-door entry with elegant cut-glass doors and retractable screens. Inside, you’ll find soaring ceilings, crown molding, and spacious living and dining areas that

  Jana DeNault Berkshire Hathaway FL Realty

  14265 Manchester Dr, Naples, FL 34114
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  $12,900 Per Month

  • 4 Beds
  • 3 Baths
  • 2,302 Sq Ft
  • House for Rent

  6172 Dogleg Dr, Naples, FL 34113

  PLAYERS CLUB AVAILABLE WITH RENTAL OF THIS HOME! Executive Retreat with privacy, Long Lake View and access to Exclusive Amenities** Located at 6172 Dogleg DR, Naples FL. 34113, this beautiful house has had a full top to bottom remodel and offers an exceptional living experience with its spacious layout and beautiful surroundings. Built in 2007, this upscale property spans 2,302 square feet under

  Rob Lahay Downing Frye Realty Inc.

  6172 Dogleg Dr, Naples, FL 34113
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  $4,250 Per Month

  • 2 Beds
  • 2 Baths
  • 1,129 Sq Ft
  • House for Rent

  784 11th St N, Naples, FL 34102

  Annual Rental available May 2026. Floors have been replaced with wooden plank style tile and main bathroom has been redone in 2026. Renovated Annual Rental in the highly sought after Lake Park Neighborhood. This quaint beach cottage is walking or biking distance to beautiful Naples' Beaches, as well as the countless restaurants and shoppes located in Downtown Naples. There are two bedrooms and

  Michael Dedio Naples Trust Real Estate Servi

  784 11th St N, Naples, FL 34102
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  $54,000 Per Month

  • 5 Beds
  • 6.5 Baths
  • 5,641 Sq Ft
  • House for Rent

  Unlisted Address

  Annual rate is $40,500 per month. Listed rate is for High Season (Nov. through April). Longer High Season leases have greater discounted rates. See attached rate sheet. Located only two blocks to the beach and featuring lush, mature tropical foliage, this classic Bermuda styled home offers absolutely stunning interiors. The sprawling residence hosts five bedrooms, a study, as well as a flex space

  Bill Earls John R Wood Properties

  Unlisted Address
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  $6,900 Per Month

  • 3 Beds
  • 2 Baths
  • 1,990 Sq Ft
  • House for Rent

  8526 Pepper Tree Way, Naples, FL 34114

  FIDDLER'S CREEK** POOL HOME - 3 BED / 2 BATH This beautiful 3 bed, 2 bath single family lake front home offers tremendous amenities in the exclusive community of Fiddler's Creek. With a large private pool and Jacuzzi (heated), upgraded kitchen, and spacious floor plan, this tastefully furnished and decorated home has it all. You can also take advantage of the great shopping, local attractions and

  Andrea Clark Premier Property Management

  8526 Pepper Tree Way, Naples, FL 34114
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  $6,500 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,096 Sq Ft
  • House for Rent

  3320 Pilot Cir, Naples, FL 34120

  Spacious Furnished 5-Bedroom Pool Home in Compass Landing – Annual or Seasonal Rental – North Naples, FL Discover exceptional living in this stunning 5-bedroom, 3.5-bath pool home located in the gated boutique community of Compass Landing in highly desirable North Naples. Offering over appx. 3000sf of modern living space, this residence provides the perfect blend of comfort, luxury, and

  NEL OZ Ozeryansky Realty One Group MVP

  3320 Pilot Cir, Naples, FL 34120
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  $42,750 Per Month

  • 4 Beds
  • 4.5 Baths
  • 3,100 Sq Ft
  • House for Rent

  354 1st Ave N, Naples, FL 34102

  Annual Rate is $32K per month. Listed rate is for High Season (November through April). Longer High Season leases have greater discounted rates. Nestled one of Olde Naples most picturesque tree-lined streets, and just three short blocks to sugar sand beaches, this idyllic and private residence affords 3,100 square feet of everything one could desire. The interior of the residence is dressed in

  Bill Earls John R Wood Properties

  354 1st Ave N, Naples, FL 34102
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  $8,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 2,942 Sq Ft
  • House for Rent

  14831 Dockside Ln, Naples, FL 34114

  AVAILABLE SEASONALLY AT $15,000 PER MONTH! AVAILABLE NOW ANNUALLY FOR $8,000 PER MONTH! THIS PET FRIENDLY AND LARGEST POOL AND LANAI (OVER 5O FT) IN ALL OF NAPLES RESERVE CAN BE YOURS TODAY! Coastal contemporary OPEN FLOOR PLAN perfect for entertaining w/extraordinary lake view. WATERFRONT LOT on 125-acre lake w/opportunity to install a private BOAT DOCK. 4 beds, 3.5 baths, 3-car tandem garage.

  Kyle Johnson Coldwell Banker Realty

  14831 Dockside Ln, Naples, FL 34114
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  $19,500 Per Month

  • 3 Beds
  • 3.5 Baths
  • 3,688 Sq Ft
  • House for Rent

  950 Galleon Dr, Naples, FL 34102

  Available from April to the end of December at $19,500 a month plus $2000 towards utilities; not available during the 2027 season. The Exquisite Port Royal estate pool home, nestled along the highly sought-after Galleon Drive, offering incredible wide water Western sunset views, and unobstructed access to the Gulf. Available starting in April until December. Can accommodate a 55 ft boat, 1000

  Dina Covato Coastal Intl Properties LLC

  950 Galleon Dr, Naples, FL 34102
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  $3,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,798 Sq Ft
  • House for Rent

  194 Wickliffe Dr, Naples, FL 34110

  AVAILABLE NOW FOR ANNUAL RENT – Experience NAPLES LIVING AT ITS BEST in the highly desirable community of WILLOUGHBY ACRES. This SINGLE-FAMILY HOME is packed with recent UPGRADES and modern finishes including a NEW ROOF, NEW IRRIGATION SYSTEM, UPDATED FLOORS, FANS, KITCHEN (2025), LIGHTING PACKAGE (2023), GUEST BATHROOM (2022), NEW AC (2020), WATER HEATER (2021), EXTERIOR PAINT (2020), and a

  John Russo Coldwell Banker Realty

  194 Wickliffe Dr, Naples, FL 34110
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  $15,000 Per Month

  • 3 Beds
  • 3 Baths
  • 2,413 Sq Ft
  • House for Rent

  15111 Pescara St, Naples, FL 34114

  Vanessa Gumm Berkshire Hathaway Florida Realty

  15111 Pescara St, Naples, FL 34114
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  $14,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,745 Sq Ft
  • House for Rent

  707 104th Ave N, Naples, FL 34108

  Casa Aria is an elegant, tropical retreat complete with all the amenities for a luxurious beach vacation! A heated pool and hot tub await you on the screened lanai, which is beautifully finished with paver brick decking and surrounded by tropical landscaping. The interior of the 3 bedroom, 2 bath home is finely appointed with high tray ceilings and bright natural colored finishes including

  Stacey Cotter John R Wood Properties

  707 104th Ave N, Naples, FL 34108
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  $45,000 Per Month

  • 4 Beds
  • 4 Baths
  • 3,394 Sq Ft
  • House for Rent

  678 11th Ave S, Naples, FL 34102

  OPEN FOR 2025-26’’ SEASON! FRESHLY REMODELED this summer, this 4+ Bedroom/ Den/4.5 bath, bayfront house is nestled between the Gulf of Mexico and Naples Bay, less than one mile to the beach, Third Street, and Fifth Avenue restaurants, shops, and galleries. This residence offers an open floor-plan, 4 bedrooms, a Den/Office area; 4.5 baths, 3 car garage, and a beautiful outdoor pool area with a

  Marjorie Workinger Royal Shell Real Estate, Inc.

  678 11th Ave S, Naples, FL 34102
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  $28,000 Per Month

  • 3 Beds
  • 3.5 Baths
  • 3,198 Sq Ft
  • House for Rent

  16476 Talis Park Dr, Naples, FL 34110

  Watercourse Villa is an impeccable single family home with a fully transferable golf membership to exclusive and coveted Talis Park! Exquisitely designed in a coastal transitional style, the home served as the model for the community and has the calming feel of a luxury resort, inviting relaxation! An open living, dining and kitchen area offers views out to the west-facing private pool and spa

  Stacey Cotter John R Wood Properties

  16476 Talis Park Dr, Naples, FL 34110
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  $10,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,869 Sq Ft
  • House for Rent

  1614 Forest Lakes Blvd, Naples, FL 34105

  Welcome to this beautiful, professionally decorated beach house in the center of Naples FL! We are about TWO MILES to the nearest beach (Clam Pass), shopping and restaurants. Fifteen minutes to downtown beaches and our famous 5th Avenue. We can accomodate short term (3night minimum) stays as well as longer term. Sorry, no pets.

  Elina Maranz Naples Vibe Realty, LLC

  1614 Forest Lakes Blvd, Naples, FL 34105
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  $7,500 Per Month

  • 3 Beds
  • 3 Baths
  • 1,947 Sq Ft
  • House for Rent

  710 Soll St, Naples, FL 34109

  Beautifull new construction home in desirable Livingston Woods, beautiful area located minutes away from dining, shops and Naples Beaches, featuring 3bedrooms/ 3bathroom 2 car garage with a living area of 1, 947sq.ft and a grand total of 2, 734 sq.ft. Fantastic home , in a prime location, circular paved driveway that allows easy access to the home, great schools! Walk through the door and witness

  Blaze Zdravev John R Wood Properties

  710 Soll St, Naples, FL 34109
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  $9,000 Per Month

  • 4 Beds
  • 3 Baths
  • 1,600 Sq Ft
  • House for Rent

  2048 Holiday Ln, Naples, FL 34104

  Discover the ultimate vacation retreat at Holiday Lane, a spacious pool home adorned with bright, modern furnishings that create an inviting and stylish atmosphere. Ideal for your Southwest Florida escape, this beautiful property offers the perfect blend of comfort, ease, and convenience. With four generously-sized bedrooms, this home accommodates up to eight guests in total comfort. While the

  Stacey Cotter John R Wood Properties

  2048 Holiday Ln, Naples, FL 34104
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  $23,600 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  605 6th Ave N, Naples, FL 34102

  Welcome to the Cypress House! Professionally decorated 3 bedroom and 2.5 bathroom home in the heart of Old Naples. The Cypress is on a quiet mahogany tree-lined street just a short walk to the beautiful beaches and refreshing waters of the Gulf of Mexico as well as popular dining, shopping, and the nightlife of Fifth Ave South. The Cypress features spacious living areas, beautiful tiled floors,

  Tom Puckett Luxury Real Estate LLC

  605 6th Ave N, Naples, FL 34102
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  $11,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • House for Rent

  2680 Longboat Dr, Naples, FL 34104

  Available for the 2026 season January through April. Welcome to the ultimate vacation rental in Naples FL! Our three-bedroom, two-bathroom house has everything you need for a relaxing and fun-filled stay. Our guests consistently tell us that we've thought of everything, and we're confident that your experience will be amazing. As soon as you arrive, you'll notice the attention to detail that sets

  Alex Belan Realty Hub

  2680 Longboat Dr, Naples, FL 34104
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  $3,850 Per Month

  • 3 Beds
  • 2 Baths
  • 1,745 Sq Ft
  • House for Rent

  6719 Crowned Eagle Ln, Naples, FL 34113

  This is available for an annual rental beginning 05/01/2022 furnished. This beautiful pool home in Masters Reserve at Lely Resort. The home has inviting spaces with a functional open-concept great room floorplan, center island eat-in kitchen with adjoining dining room. Spacious Master Suite with water views. Enjoy relaxing or entertaining on the large lanai with a heated pool overlooking gorgeous

  Kevin Fischer Star Rental & Property Mngt

  6719 Crowned Eagle Ln, Naples, FL 34113
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  $15,000 Per Month

  • 4 Beds
  • 3 Baths
  • 1,680 Sq Ft
  • House for Rent

  659 108th Ave N, Naples, FL 34108

  This fully remodeled 4 bedroom, 3 bathroom home combines clean modern design with the relaxed vibe people love about Naples. Inside, every room feels fresh, bright, and thoughtfully finished – from the sleek open-concept living area to the beautifully updated bedrooms and baths. Smart home touches and state-of-the-art technology make everything easy, whether you’re streaming a movie after the

  Keith Ponsler Naples Vacation Properties

  659 108th Ave N, Naples, FL 34108
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  $11,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,563 Sq Ft
  • Apartment for Rent

  5891 Haiti Dr, Naples, FL 34112

  Available Jan 2027 at $11,000| Available Nov-Dec 2026 at $7,500 | Welcome to this breathtaking coastal-style home in the prestigious, award-winning Isles of Collier Preserve. Fully furnished, this open-concept home boasts two beautifully appointed bedrooms with two luxurious bathrooms, a dedicated dining area, and a versatile office/den area with an inviting daybed and trundle. Whether you're

  Patrick Burke Halo Home Management LLC

  5891 Haiti Dr, Naples, FL 34112

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