Vacation Villa Rentals By Owner In Naples, FL

$1705.73

Brand new 4bdr Villa in Old Naples - walking distance to Beach

Naples, Florida, United States

Introducing Swiss Miss - a brand-new luxury rental home nestled within the serene landscapes of Naples, Florida. Designed to epitomize modern elegance and coastal charm, this exquisite residence offers an unparalleled retreat for those seeking opulence and tranquility.brLocated in Old Naples, Swiss Miss is steps away from the shimmering Gulf of Mexico and from the bustling 5th Ave with all its delicious restaurants and cool shops. The exterior of the home is a masterpiece of modern Key West architecture that seamlessly blends with the surrounding natural beauty.brUpon entering, guests are greeted by a grand open room adorned with luxurious accents and designer furnishings. The open-concept living area exudes sophistication, with soaring ceilings, custom lighting fixtures, and floor-to-ceiling windows that flood the space with natural light. brThe gourmet kitchen is a chef's delight, equipped with top-of-the-line appliances from Miele and SubZero, marble countertops, and an oversized island perfect for culinary endeavors and casual dining. Adjacent to the kitchen, the formal dining area provides an elegant setting for intimate gatherings and memorable meals.brThe master suite is a sanctuary of indulgence, featuring a king-sized bed draped in fine linens, two spacious walk-in closets, and a direct access to the outside pool. The ensuite bathroom is a lavish retreat, complete with a freestanding soaking tub, a glass-enclosed rain shower, and dual vanities adorned with designer fixtures.br3 additional guest suites upstairs offer luxurious accommodations for family and friends, each appointed with plush bedding, ample storage space, and private bathrooms featuring high-end finishes and amenities. two of the suites have their own balconies and one of the suites an adjacent office. There is another spacious office downstairs.brOutside, Swiss Miss is a haven for outdoor living and entertaining. A sprawling terrace beckons with a pool, sun loungers, and a covered dining area with a built-in barbecue grill - perfect for al fresco meals and sunset soirees. brSwiss Miss is just steps away from the beach and guests can use all beach equipment from the house. The house has a garage for 2 cars.brWith its unparalleled amenities and idyllic location, Swiss Miss sets a new standard for luxury living in Naples, Florida, promising an unforgettable retreat for discerning travelers seeking the ultimate in comfort, style, and relaxation.brNAPLES LAW: we are only allowed to rent the property for a 30 day min, with an exepction for a 2 week rental twice a year. So please ask about 2-4 week rental periods.

4

Bed

5

Bath

8

Sleeps

Select Dates for Price

Villa

2BR/2BA Fully Updated Villa 3 mi Downtown, Hospitals, Beaches, Pickelball

Naples, Florida, United States

Escape to this charming villa in picturesque Naples. This awesome property features 2 bedrooms with a king bed and a full bed, ensuring a soothing night's sleep for guests. With amenities like heating, AC, a hair dryer, your stay will be comfortable and convenient. We hope you enjoy what our place and Naples has to offer.brbrMinimum 90 day rentalbrbrThis fully renovated, ground-level condo has two bedrooms and two bathrooms, offering 1,180sqft of clean, functional space. The unit was completely redone in April 2024; everything is new and turnkey. The open layout feels bright and airy, with wood-look tile floors, ceiling fans throughout, and a thoughtful setup for remote work and relaxing downtime.brbrThe living room includes an L-shaped couch, two chairs, a corner workspace, a 70 smart TV, and a dining table that seats six. The kitchen is fully equipped, it has a quartz countertop, a breakfast bar with stools, full-size appliances, plenty of cabinets, and all the tools and utensils you'd need. Both bedrooms have nightstands, dressers, and Bahamas shutters. The primary bedroom features a king-size adjustable bed, a walk-in closet, a smart TV, and an en-suite bathroom with a walk-in shower and a single vanity. The second bedroom has a double bed, a closet, and its own en-suite bathroom with a shower/tub combo and a single vanity.brbrA laundry closet with a washer and dryer, central A/C and heating, high-speed Wi-Fi, and utilities are included. Out back, you've got your own 160sqft concrete patio with a table, chairs, and umbrella, perfect for coffee or a wind-down drink. A Ring light and front door security system add peace of mind.brbrThe condo is just steps from the complex's swimming pool. Your two assigned parking spots right in front, plus guest parking. If you're into boating, kayaking, or fishing, there's a dock for up to a 20' boat and water access from the community.brbrWhether you're staying for 3 months or the entire season, this spot is set up to make your time in Naples easy, comfortable, and relaxing. It offers all the space, privacy, and extras that make it feel like home. Book your stay now!

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$366.3

/ Nightly

Villa

Gorgeous 2nd Floor Unit in The Quarry, Minutes to downtown Naples and Mercato.

Naples, Florida, United States

Newly furnished 3 bedroom 2 1/2 bath condo with Den in The Quarry. Sleeps 8 comfortably. Bright, airy, clean and all furnishings and appliances are new for 2024. Lanai with view of the conservation area where deer and turkeys come and visit you. The Quarry community is one of the most active in all of North Naples. You'll have access to amenities galore with 2 community pools, hot tubs, plus tennis, pickle ball and bocci courts, and a brand new gym overlooking the lake. You will be 20 minutes to Vanderbilt Beach , Mercato, and downtown Old Naples. 25 minutes from Fort Myers Int’l Airport.brbrbrRoom Details:brbr• The large family room is light and airy with sliders leading to the screened in Lanai for extended living. 10' tray ceiling and ceiling fans. New large flat screen smart TV and comfortable seating.br• The kitchen is fully equipped with granite countertops and new LG appliances. Seating for 4 in the kitchen nook and seating for 6 in the dining room.br• Master Bedroom has King size bed and triple dresser with walk in closet. Master bathroom has a large soaking tub, his and hers vanities and a tiled shower.br• Second Bedroom has a Queen size bed, dresser and walk in closet.br• Third Bedroom has 2 Twin beds, dresser and closetbr• Office/Bedroom has a Queen size pull out sofa, adjustable height desk, chair and smart TV.br• Secondary bathroom has walk-in shower.br• Powder Room has pedestal sinkbr• Lanai is screened in with 2 ceiling fans. It is furnished with a 4- seat high top table, loveseat, 2 chairs and a cocktail table.brbrbrAdditional Details:brbr• Parking for 2 carsbr• Ceiling Fans in every roombr• Washer/Dryerbr• High-speed wireless internetbr• Gas Grillbr• 2 Bicyclesbr• 2 Pickle ball racketsbr• Beach towelsbr• Beach umbrellabr• All linens includedbr• Dishes, Glassware, Silverwarebr• Beach Club AccessbrbrPolicies:br• No smokingbr• No pets allowedbr• No events, parties or large gatheringsbr• Must be at least 25 years old to rentbrbr

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$541.51

/ Nightly

Villa

Naples Luxury Villa, Huge Pool, 2 Pickleball Courts, Full Acre of Total Privacy

Naples, Florida, United States

Escape to a rare Naples luxury retreat where refined design, complete privacy, and expansive outdoor living come together on more than a full acre of lush, gated grounds. Surrounded by over 600 mature trees, this private Naples vacation rental offers a true estate experience that feels worlds away—yet remains just minutes from Naples beaches, Fifth Avenue South, and the area’s most sought-after dining and shopping. This is not simply a vacation home; it is a secluded compound designed for relaxation, entertaining, and unforgettable memories.brbrAt the heart of the home is a sprawling open-concept great room that seamlessly connects the living, dining, and kitchen spaces. Natural light pours in through oversized windows, with sweeping views across the tropical grounds. The layout invites effortless connection from every angle, making it ideal for both intimate stays and larger gatherings.brbrThe oversized chef’s kitchen is a true showpiece. Designed for both elevated entertaining and everyday indulgence, it features a premium Thermador gas range, expansive prep and serving areas, two striking brass sinks, and a statement brass pot filler at the stove. The kitchen flows seamlessly into both the great room and outdoor entertaining areas, creating a natural indoor-outdoor lifestyle.brbrThe primary suite is a private sanctuary. Unwind in a king-size bed dressed in Frette sheets and duvets, widely regarded as among the finest in the world. The suite features a newly completed luxury en suite bathroom, finished floor-to-ceiling in white marble, with a spacious two-person walk-in shower and dual rain shower heads for a spa-like experience.brbrThe second bedroom offers a queen bed with serene views of the garden and water fountain. The bunk room comfortably accommodates up to six guests with two queen beds and two upper bunks, making it ideal for families or group stays. Two additional full bathrooms are centrally located and easily accessible from all guest rooms.brbrStep outside to experience over an acre of ultra-private outdoor living—an exceptional rarity in Naples vacation homes. Enjoy the resort-style pool with a cascading waterfall, a private tennis and pickleball court, an orchid garden, and multiple outdoor lounge and dining areas. The expansive tropical patio comes alive in the evenings with hundreds of solar and string lights, creating the perfect setting for outdoor dining, conversation, and stargazing. White terry cloth-covered chaise lounges, plush robes, and slippers are provided for every guest.brbrEvery detail has been thoughtfully considered to create a seamless stay. Beach towels, chairs, and umbrellas, as well as tennis and pickleball equipment, are all included. When you choose to explore, some of Naples’ most beautiful beaches are just a short 12-minute drive away, including Lowdermilk Beach, Vanderbilt Beach, and Naples Beach Pier.brbrThis private Naples estate offers the space, design, and level of privacy rarely found in the area, delivering an elevated experience defined by comfort, beauty, and lasting memories.brbr⸻brbrImportant House Notesbr • Owners reside on a separate property at the rear of the estate. While nearby if needed, guest accommodations and outdoor spaces are completely private. The only shared area is the front driveway.br • The pool is not heated.br • Sports court hours are 10:00 AM to dusk.br • While this home is offered as a vacation rental, neighboring properties are not. We kindly ask all guests to respect the peace and tranquility that the surrounding community values and expects.br • Guests are asked to feed the koi fish in the pond daily.br • Guests are also asked to water select outdoor potted plants during their stay.br • For your enjoyment and convenience, the owners have thoughtfully curated an exceptional in-home wine selection, featuring a variety of whites, Prosecco, Champagne, and distinguished reds from notable regions. A beautifully presented wine menu is available at the home, allowing you to effortlessly select and enjoy the perfect bottle without ever needing to leave the property.

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$313.18

/ Nightly

Villa

Beautiful, Remodeled Villa Within Walking Distance to Vanderbilt Beach!!

Naples, Florida, United States

Your Naples adventure begins at this beautifully remodeled highly sought after Beachwalk 2-bedroom villa!! Walking distance to Vanderbilt Beach and many restaurants and shops! Access to 2 beautiful outdoor pools. brAccepting long-term rentals for the 2026 Winter Season! brOur condo has everything you need and more! New in 2025 the kitchen and bathrooms have been upgraded with shaker cabinets, granite countertops and a new faucet and sink, new stainless steel appliances, updated paint, new lighting/fixtures, and modern furniture/décor/linens. You can enjoy a 15-minute walk or 3-minute drive to La Playa, Turtle Club and the Ritz Carlton.brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 2 twin bedsbrbrMAIN FEATURESbr- Large sofa/loveseat/ recliner chair br- Dining tablebr- 2 screened lania's br- 2 beach chairs, pool floats, beach toysbr- Community pool access brbrKITCHENbr- Refrigerator, stove/oven, dishwasher, microwavebr- Drip coffee maker (bring your own coffee)br- Cooking basics, dishware & flatwarebrbrGENERALbr- Free WiFi, keyless entrybr- Central A/C & heating, ceiling fansbr- Linens & towels, trash bags & paper towelsbr- Hair dryer, hangers, iron & boardbrbrbrPARKINGbr- Garage space for 1 br- Additional uncovered guest parkingbrbr-- THE LOCATION --brbr- 3/4 mile to Vanderbilt Beach br- 1/4 mile to Mercatobr- 8 miles to 5th Avenue South: shopping, dining, art galleries, nightlife

2

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2

Bath

4

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$363.84

/ Nightly

Villa

Naples best location, heated pool, close to the beach, gated community .

Naples, Florida, United States

If you are looking for relaxing place - you found it! Private, heated pool to enjoy with family or friends, 4 bedrooms, smart TV, Apple TV and Roku to enjoy your favorite movie in the evening. Home is truly home away from home. It is VILLA but very private. Master bedroom with king size bed and own bathroom. 2 other bedrooms with queen size beds. 4 th bedroom has a twin bed and a couch. Fully equipped kitchen, outdoor table and chairs, BBQ will help you to enjoy it all Naples can offer. Beach chairs, umbrella and cooler will help you to enjoy Naples beautiful beaches. This house located 7 min away from Vanderbilt beach, 5 min to Marcato with restaurants and movie theatre.

4

Bed

2

Bath

6

Sleeps

$206.71

/ Nightly

Villa

30-day minimum lease | Carlton Lakes | 2bs/2ba | Furnished Villa w/ Den

Naples, Florida, United States

Welcome to your dream villa in the exciting Carlton Lakes community! This fully furnished vacation rental boasts an open floor concept with two charming bedrooms, an inviting den, an office area with a fully equipped work station, and two beautiful bathrooms. The kitchen, stocked with all the essentials, overlooks stunning water views to inspire any chef. Situated in a vibrant community nestled amidst nature, you'll relish the abundance of amenities it offers.brbrHaloHome aims to provide an exceptional, hotel-like experience for all of our guests. We are available to answer your questions and provide assistance via email or phone.brbrCarlton Lakes provides community pools, bocce and tennis courts, walking/biking trails, a private fishing pier, and barbecue areas within a protected preserve, making this oasis a perfect place to rejuvenate and recharge. Just a short 13-minute drive to Delnor Wiggins Beach and a leisurely walk to the renowned Seed to Table, immerse yourself in everything North Naples has to offer, while only 25 minutes from downtown Naples, renowned for its cultural attractions, shopping, dining delights, and white sand beaches. This retreat has everything to make your Naples vacation unforgettable.brbrThere is a smart lock on the home for keyless entry. The home's garage has space for one car. Overnight parking on the driveway or street is not allowed.brbrHaving a car is recommended. Uber, Lyft, and local cab services are also available.brbrMinimum lease term is 30 days.

2

Bed

2

Bath

4

Sleeps

$299.15

/ Nightly

Villa

30-day minimum lease | Isles of Collier | 3 bedrooms | den with a pull-out couch | 2 baths

Naples, Florida, United States

Nestled in the award-winning Isles of Collier Preserve, this contemporary coastal style villa boasts three elegantly furnished bedrooms, a versatile office/den area with pull-out couch, and two beautiful bathrooms. It comes fully equipped with sophisticated furnishings and all necessary conveniences, making it ideal. The outdoor lanai is the crown jewel, providing a serene spot to relax poolside and admire the stunning lakefront sunrises.brbrHaloHome aims to provide an exceptional, hotel-like experience for all of our guests. We are available to answer your questions and provide assistance via email or phone.brbrGuests access the home using contactless check-in via smart lock. brCheck-in: 3:00pm ESTbrCheck-out: 11:00am ESTbrbrTucked away within the community, surrounded by scenic walking and biking trails, this retreat is the ultimate escape. The community offers a wealth of amenities including a clubhouse, both resort-style and lap pools, a state-of-the-art fitness center, and courts for tennis and pickleball. Just 15 minutes away, this prime location ensures easy access to the bustling heart of downtown Naples, famous for its cultural venues, exquisite shopping, gourmet dining, and pristine beaches.brbrGuests can access the home using contactless check-in via smart lock. brCheck-in: 3:00pm ESTbrCheck-out: 11:00am ESTbrbrHaving a car is recommended. Uber, Lyft, and local cab services are also available.brbrShort-term availability, priced at $10,000 per month during the season and $4,500 during the off-season. Minimum lease term is 30 days.

3

Bed

2

Bath

6

Sleeps

$158.2

/ Nightly

Villa

90-day minimum lease | Azure | 2bd+den/2ba |Furnished villa

Naples, Florida, United States

Welcome to your dream villa in the serene paradise of Azure at Hacienda Lakes! This fully furnished haven boasts two cozy bedrooms, an inviting den with a full work station and daybed that can be transformed as an office or additional bedroom, and two luxurious bathrooms. Make sure to soak in the view and savor the outdoors while grilling on this new expanded lanai. Situated in a vibrant community, you'll relish in the abundance of amenities it offers. brbrHaloHome aims to provide an exceptional, hotel-like experience for all of our guests. We are available to answer your questions and provide assistance via email or phone.brbrGuests access the home using contactless check-in via smart lock. brCheck-in: 3:00pm ESTbrCheck-out: 11:00am ESTbrbrThe clubhouse is a hub of activity, featuring a resort-style swimming pool to unwind, a state-of-the-art gym, tennis and pickleball courts for the sport enthusiasts, and a gathering room complemented by a catering kitchen for hosting memorable gatherings. Not only does this villa offer a blissful escape, but it also provides convenience with its proximity to both the bustling charm of 5th Avenue and its famous white sand beaches, and the peaceful tranquility and adventure of Marco Island both within 20 minutes away!brbrHaving a car is recommended. Uber, Lyft, and local cab services are also available.brbrShort-term availability, priced at $2,600 per month. Minimum lease term is 90 days!

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$345.42

/ Nightly

Villa

‘Pelican Nest’, Tropical Naples Villa w/ Pool

Naples, Florida, United States

Navigate to the beautiful city of Naples for beach lounging, urban exploring, and carefree relaxation at this delightful getaway. Shrouded in the privacy of lush palm trees, the fenced-in backyard of this updated 4-bedroom, 3-bathroom vacation rental offers a private pool that can be heated, screened-in porch, gas grill, and patio for the ultimate family retreat. You’ll be ideally situated to many golf courses, downtown fun, and Naples Beach to get a taste of every rave-worthy attraction nearby.brbr-- THE PROPERTY --brbrGas Grill | Furnished Screened-In Porch | 2.5 Mi to Downtown | High Chair & Crib | Beautifully RemodeledbrbrBedroom Suite 1: King Bed | Bedroom Suite 2 (w/ Separate Entrance): King Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Beds | Additional Sleeping: CribbrbrVILILA HIGHLIGHTS: Heated pool (depth 3’ - 6’, heated w/fee), furnished patio, Smart TVs w/ cable, dining room, vanity area, ceiling fanbrKITCHEN: Fully equipped, cooking basics, microwave, toaster, drip coffee maker, trash bags, paper towels, high chairbrGENERAL: Free WiFi, washer/dryer, iron & board, towels & linens, complimentary toiletries, hair dryer, central A/CbrFAQ: Half-step to access, optional nightly pool heat fee (paid pre-trip, applied to entire stay, does not apply to stays 7+ nights between December 2025-March 31, 2026)brPARKING: Driveway (2 vehicles), free street parkingbrbr-- THE LOCATION --brbrBEACHES: Naples Beach (2.9 miles), Lowdermilk Park (3.9 miles), Clam Pass Park (7.1 miles), Vanderbilt Beach (11.3 miles)brNAPLES HOT SPOTS: Naples Bay Resort Restaurants (1.1 miles), Capt Joey D Charters (1.3 miles), The Cabana Bayfront (restaurants & bars, connecting tunnel pathway, 1.6 miles), Naples Train Museum (1.6 miles), Tin City (1.8 miles), 5th Avenue (Evening on 5th w/ live music, shopping & dining, 2.0 miles), Downtown Naples (2.5 miles), Third Street South Farmers Market (Thursday on 3rd w/ live music & entertainment, 3.0 miles), Naples Zoo at Caribbean Gardens (3.5 miles), Golisano Children's Museum of Naples (10.3 miles), Sun-N-Fun Lagoon (10.3 miles)brOUTDOOR DESTINATIONS: Cambier Park (2.2 miles), Naples Botanical Garden (2.8 miles), Conservancy of Southwest Florida (3.2 miles), The Naples Preserve (3.6 miles), Freedom Park (3.9 miles), Delnor-Wiggins Pass State Park (13.2 miles)brHIT THE LINKS: The Glades Golf & Country Club (2.3 miles), Lakewood Country Club (2.9 miles), Foxfire Country Club (2.9 miles), Glen Eagle Golf & Country Club (3.3 miles), Naples Grande Golf Club (3.6 miles), Hibiscus Golf Club (4.0 miles), Tiburon Golf Club (8.1 miles), The Naples Beach Hotel & Golf Club (9.5 miles)brFISHING GUIDES: A and B Deep Sea Fishing Charters (1.4 miles), Dalis Fishing Charters, Inc (2.5 miles), Captain Marvel Charters (15.4 miles)brAIRPORTS: Naples Airport (1.5 miles), Southwest Florida International Airport (31.2 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowedbr- No events, parties, or large gatherings br- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: There is an optional pool heat fee of $75/night (+ fees & taxes, paid pre-trip, applied to entire stay). The pool heating fee will not apply for stays of 7 nights or more booked between December 2025 and March 31, 2026

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Bath

Sleeps

$433.18

/ Nightly

Villa

Min 2 Beach Dining Pool 8 ppl Lux Family Villa

Naples, Florida, United States

Summary:brbr***LUXURY FAMILY VILLA IDEAL FOR FAMILIES (SLEEPS 8)***brbrbrbrYOU MADE IT! You are now viewing a very special/unique property right in the heart of beautiful Naples Florida! Here are some of the properties key features:brbrbrbr-Fully Covered Heated Poolbrbr-3 Minutes Walking Distance To Beachbrbr-3 Minutes Walking Distance To Shopping, Dining, Nightlifebrbr-On Site Washer/Dryerbrbr-Grill For Your Cooking Needsbrbr-Outdoor Dining Area (Seats 10)brbr-Bikes & Beach Chairs brbrbrbr& so much more!brbrbrbrThe Space:brbrThe Space:brbrbrbrWe wanted this space to be very relaxing and comfortable for our guests to enjoy in the heart of Naples Florida very close by to everything you may need to have a great and relaxing time!brbrbrbrIn the backyard area we have a heated saltwater pool for you so you, your family, and friends can enjoy being out in the beautiful Florida sun. We also have a big dining table outside that seats 10 with grill so you and your family/friends can enjoy meals outside. brbrbrbrThis villa is stocked with everything you may need in the kitchen for your daily kitchen needs. brbrbrbrCoffee maker in the kitchen for a quick pick me up throughout the day or in the morning. brbrbrbrOn site washer/dryer to make sure your families/friends clothes are washed and dried. brbrbrbr5 total TV's (3 in bedrooms, 1 in living room, & 1 in outdoor backyard/patio area) to either watch movies with family/friends or put on some music!brbrbrbr3 bedrooms (All have King Beds)brbrbrbr2 double size sofa beds. brbrbrbrHigh speed WIFI throughout the home and backyard!brbrbrbrLastly, in the garage we have bikes & beach chairs. brbrbrbrThe Neighborhood: brbrbrbrThe Naples Park neighborhood in Naples is a very safe neighborhood located right next to the ocean and everything dining, nightlife, and shopping related you may need during your stay. brbrbrbrOther Things to Note:brbrbrbrDisclaimer: For your safety and the safety of others, we have motion activated surveillance cameras installed outdoors at this property. brbrbrbr1. We have a doorbell camera. brbrbrbr2. We have one by the garage pointing towards the driveway. brbrbrbr3. We have one in our pool area.brbrbrbrGuest Access:brbrGuests have access to the whole property!brbrbrbrThe Neighborhood:brbrWelcome to Naples Park! Just minutes away from Vanderbilt Beach, this family-friendly neighborhood offers a safe and convenient location for your stay. Enjoy the sun, sand, and surf without having to travel far.brbrbrbrNaples Park has it all - from a variety of dining options to shops and grocery stores within walking distance. Indulge in delicious cuisine and find everything you need right at your fingertips.brbrbrbrOutdoor enthusiasts will love the picturesque sidewalks for strolling or biking, as well as nearby parks for picnics and games. Golfers can also enjoy several courses in the area.brbrbrbrDon't miss out on the opportunity to create lasting memories in Naples Park. Book your stay now and experience the best of this wonderful community by the beach.brbrbrbrGetting Around:brbrGetting around in Naples Park is a breeze, thanks to its convenient location and various transportation options.brbrbrbrIf you prefer to explore the neighborhood on foot, you'll find that many attractions, restaurants, and shops are within walking distance. Take a leisurely stroll to Vanderbilt Beach just minutes away, and soak up the sun or enjoy a refreshing swim in the Gulf of Mexico.brbrbrbrFor those who want to venture further, renting a bike is a popular and eco-friendly option. Naples Park features well-maintained sidewalks and bike lanes, making it safe and enjoyable to cycle around the area. You can easily rent bicycles from local shops or through bike-sharing programs.brbrbrbrIf you prefer to drive, there are plenty of parking options available in Naples Park. Whether you're driving your own vehicle or renting a car, you'll have no trouble finding parking spots near the beach, restaurants, and other attractions. Exploring Naples and its surrounding areas by car allows you the freedom to visit nearby attractions such as the Naples Zoo, Delnor-Wiggins Pass State Park, or the scenic Naples Pier.

3

Bed

3

Bath

8

Sleeps

$164.99

/ Nightly

Villa

Coastal Retreat in Windstar | Social Membership Available

Naples, Florida, United States

Welcome to your perfect Naples getaway in the exclusive Somerset community at Windstar on Naples Bay! This beautifully styled 3-bedroom, 2-bath vacation home offers a relaxed coastal vibe with elegant touches throughout—thoughtfully designed to provide comfort, convenience, and a true sense of escape. Ideal for couples, families, or small groups, this bright and breezy retreat invites you to unwind and enjoy the very best of Southwest Florida living.brbrStep inside to find soaring vaulted ceilings, sun-filled open living areas, and a fully equipped kitchen with a spacious island—perfect for casual meals, morning coffee, or evening entertaining. The open-concept layout flows seamlessly into the large, screened lanai, creating an effortless indoor-outdoor living experience. Whether you're sipping cocktails at sunset, hosting friends for dinner, or simply enjoying a quiet morning, the serene outdoor spaces—including a private, enclosed courtyard—offer the perfect backdrop.brbrThis home comfortably sleeps up to six guests with three well-appointed bedrooms designed for rest and flexibility. The spacious primary suite features a plush king bed, cozy sitting area, two large closets, and a spa-like en suite bath with double vanities, a walk-in shower, and a soaking tub—plus private access to a tranquil patio. The second bedroom also offers a king bed and generous storage, with a full bathroom conveniently located just outside the door. The third bedroom includes a queen-size pullout sleeper sofa and doubles perfectly as a den or home office for those working remotely or needing extra space.brbrResidents can enjoy the Windstar Social Membership which grants access to four exquisite dining venues, premier tennis and bocce courts, a state-of-the-art fitness center, access to the private beach, the Keewaydin boat shuttle service, and exclusive club events—offering an unparalleled lifestyle of elegance.brbrWhether you're here to soak up the sun, explore downtown Naples, or simply relax in comfort and style, this vacation home has everything you need for an unforgettable stay.brbrAMENITIES: Somerset offers a charming pool area complete with a relaxing hot tub, ideal for unwinding in style. Rental of Somerset also includes the exclusive opportunity to transfer the prestigious Windstar Social Membership. This elite membership grants access to four exquisite dining venues, premier tennis and bocce courts, a state-of-the-art fitness center, unlimited entry to the private beach, the Keewaydin boat shuttle service, and exclusive club events—offering an unparalleled lifestyle of elegance.brbrASSOCIATION APPLICATION/FEE: An application and/or background check may be required for rentals within the community. This may incur processing fees not included in the rental reservation.brbrSEASON BOOKING DETAILS: A 2 month minimum is required January-April.brbrThe Holiday Life is a full service luxury vacation and seasonal rental management company with an expansive portfolio - from beachfront, to downtown and amenity rich communities throughout Naples and Marco Island. Our team is here to assist in every step of planning your experience from choosing the perfect rental, pre arrival planning, dedicated concierge services and 24/7 support during your stay. We look forward to the opportunity to host you! brbrRENTAL PURPOSE: This property is intended for single-family and transient guest rentals only - any requests for work crews require specific approval prior to booking. No commercial vehicles or work trucks may be parked on site. brbrCOMMERCIAL USE: Commercial and/or business use of the property is not allowed, including commercial photography or filming. brbrMINIMUM AGE REQUIREMENT: Primary guest whose name is associated with this booking must be at least 25 years of age and must be present for the duration of the reservation. brbrGUEST LIST: A guest list including full names and ages of all people who will be staying overnight must be provided in writing at least 24 hours to the guest(s) arrival.

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Sleeps

$310.47

/ Nightly

Villa

Charming 4-bedroom plus den villa with pool and spa near the beach and downtown.

Naples, Florida, United States

Unwind gazing at the stars or the sky, enjoying the massaging jets in the hub tub surrounded by luscious greenery and your favorite people. Feel confortable in this 4 bedrooms plus den home with salt water, heated beach entry pool with fountains and spa. The property has an ample fenced backyard and parking space. Located close to the beach, Downtown Naples/ 5th Ave S. and most attractions. Walkable to dining and shopping.

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Sleeps

$103.6

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Villa

Sea Shell Villa 1

Naples, Florida, United States

Your family will be close to many beaches, restaurant, shops and so much more when you stay at this centrally located villa. Our Villa is fully upgraded. The living has a sofa sleeper which has an extra cushioned mattress for relaxing comfort. The tv is 65”. In the dining area we have a table with 4 chairs and a fully stocked kitchen. Next to the kitchen there is a nice sized launder room which has a full sized washer and dryer. In the laundry room there are beach chairs and a beach cart for your beach adventures. In the hallway there is a linen closet with extra bath towels, beach towels and extra pillows. In the 1 bedroom we have a queen sized bed with another 65” tv. Finally in the front porch there are 2 chairs and a table and it is all screened in.

1

Bed

1

Bath

4

Sleeps

$276.98

/ Nightly

Villa

Luxury 3,000 Sq Ft Home with Pool in Esplanade Hacienda Lakes, South Naples

Naples, Florida, United States

Experience the epitome of luxury in this immaculate 3-bedroom, 3-bathroom home nestled in the prestigious Esplanade Hacienda Lakes community. Just 15 minutes from Naples' lively 5th Avenue, Naples Pier Beach, and Isles of Capri, and 22 minutes to Marco Island’s stunning beaches and dining, this home offers both elegance and exceptional convenience. Located a mere mile from Publix and close to numerous restaurants and shops, it’s the perfect blend of relaxation and exploration.brbrProperty Highlights:brbrSpacious Bedrooms: Two master suites with king-size beds and ensuite baths, plus a queen suite with a private bathroom.brExtra Space: A cozy den for work or leisure.brOutdoor Living: Enjoy a heated pool, outdoor kitchen, and screened lanai with stunning sunset views.brStroll to the clubhouse for resort-style amenities, including a gym, spa, pool, pickleball, tennis, bocce, and a dog park.brbrPet-Friendly: One small dog (under 25 lbs) is welcome with a $600 deposit.brbrEmbrace the tranquility of this gated community and soak in South Naples' sunny charm and breathtaking sunsets.

3

Bed

3

Bath

6

Sleeps

$200.52

/ Nightly

Villa

Brand New Naples Villa in a Resort Style gated community!

Naples, Florida, United States

Consider this villa your home away from home while you visit Naples. This gorgeous villa features three bedrooms, including two king beds and a sofa bed in the office space, offering plenty of room for guests to relax. With two bathrooms equipped with hair dryers, getting ready is a breeze. The perfect balance of comfort and convenience awaits, with heating and AC to keep the temperature just right. Whether you’re working or unwinding, this excellent space adapts to your needs. Make your holiday one for the books with a stay at our place. Full access to all the resort has to offer. Full gym, spa and large pool and Bahama Bar with full menu!

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Bath

Sleeps

$1555.48

/ Nightly

Villa

Luxurious 7-bedroom villa with pool/spa and pickleball court in fabulous Naples

Naples, Florida, United States

Spacious Contemporary Villa with Luxe Pool, Private Pickleball Court & Total Seclusion. Nestled in a serene setting, this modern retreat offers expansive indoor and outdoor living areas designed for relaxation and connection. Lounge by the sparkling private pool, enjoy a match on your very own pickleball court, or simply unwind in the peaceful seclusion of the beautifully landscaped grounds. Every detail has been thoughtfully curated—from sleek, high-end finishes to comfortable designer furnishings—to offer travelers a refined yet welcoming experience. Whether you’re planning a family vacation, a couples’ escape, or a group retreat, this villa provides the perfect balance of leisure, style, and exclusivity.

7

Bed

4

Bath

20

Sleeps

$211.28

/ Nightly

Villa

Grand 4/3 pool home with beautiful lake sunset views minutes from the beach!

Naples, Florida, United States

Everyday living feels like a luxury getaway. This stunning 4 bedroom plus den, 3 bathroom residence is perfectly designed for those who appreciate comfort, elegance and the Florida outdoor lifestyle. brbrStep inside to discover spacious light-filled living areas ideal for both relaxing and entertaining. The thoughtfully designed floor plan offers generous bedrooms, beautifully appointed bathrooms and seamless indoor-outdoor flow that defines Southwest Florida living. brbrThe open kitchen concept where style meets function beneath soaring cathedral ceilings that create and airy expensive feel. Outside, your private oasis awaits. brbrEnjoy the sparkling heated pool and spa, perfect for sun-soaked afternoons and stunning sunsets. brbrFifteen minute drive to Naples downtown best shops &restaurants and a few more to its beautiful beaches.brbrThis is more than a home. It is the Naples dream for you and your family.

Bed

Bath

Sleeps

$284.72

/ Nightly

Villa

Beautiful spacious villa in sunny Naples!

Naples, Florida, United States

A 3 bedroom, 2 bathroom villa in the secure, gated resort style community of Winding Cypress, NaplesbrbrThe Area: Naples in Southwest Florida is know for its abundant sunshine, white sand beaches, shelling, fishing, golf, shopping and fine dining.brbrThe Location: 15 minutes to Marco Island, 20 minutes to historic downtown Naples and the beaches. Fort Meyers, Sanibel Island, the Everglades and even vibrant Miami are all within an easy day's exploration.brbrThe Villa: Newly built and spacious, the villa features a two car garage with easy entry into the villa, a separate laundry room, a master bedroom with king bed and ensuite bath having tiled walk-in shower, a second bedroom with queen bedding and adjacent bath, and a den with a full pull out sofa. The kitchen has a large granite counter area and is fully equipped with stainless steel appliances and all of the comforts of home. The living areas are furnished with Italian design furniture and soft leather lounge seating. There are two smart TVs in the unit. The Florida living extends outside with an oversized screened- in lanai overlooking a private and quiet nature preserve. A conversational fire pit, gas barbecue grill and sun loungers make the lanai a wonderful outdoor retreat. Ceiling fans are found throughout the villa as well as central air and heat.brbrThe Community: Guests will enjoy access to all resort amenities. These include a heated pool with lap lanes, an adjacent spa, a state of the art gym, tennis, bocce ball and pickle ball courts, a poolside barefoot bar and cafe and a full activities center. The community offers miles of recreational trails around lakes and preserve for walking, running and biking.brbrCome and enjoy sunny and warm Southwest Florida!

Bed

Bath

Sleeps

$206.14

/ Nightly

Villa

Coastal Cottage at Isles of Collier Preserve! Pickleball Resort Pools & Beaches

Naples, Florida, United States

Experience resort-style living in one of Naples’ premier gated communities — The Isles of Collier Preserve. Ideally located just minutes from Downtown 5th Avenue, Gulf beaches, golf courses, and Marco Island, this newly built coastal retreat offers the perfect blend of luxury, relaxation, and convenience for your extended Naples stay.brDesigner-furnished in a fresh modern coastal style, this 2024-built cottage comfortably accommodates up to six guests with 2 bedrooms, 2 bathrooms, and a private den/office. Thoughtfully designed for both entertaining and everyday comfort, the bright open-concept living area features soaring ceilings, elegant finishes, and a 75” smart TV visible throughout the main living spaces.brThe spacious kitchen and dining area are ideal for gathering, offering seating for eight at the dining table plus additional seating at the oversized island.brSleeping Arrangements++brThe tranquil primary suite features a king bed, 55” TV, and a luxurious ensuite bath designed for comfort and privacy.brThe guest bedroom offers a queen bed with convenient access to the second full bathroom.brThe private den/office, enclosed with French doors, includes a queen sleeper sofa, desk workspace, and 55” TV — perfect for remote work or accommodating additional guests.brA two-car attached garage and step-free entry provide added ease and convenience.brOutdoor Living++brEnjoy Naples’ beautiful year-round weather from the expansive screened lanai overlooking lush tropical landscaping. The outdoor space includes dining for six, additional lounge seating, and relaxing swivel glider chairs — ideal for morning coffee, evening cocktails, or entertaining friends and family.brResort Community Amenities++brThe Isles of Collier Preserve is a luxury master-planned community celebrated for its natural beauty and exceptional amenities across 2,400 acres.brGuests enjoy access to ++brResort-style pool & lap poolbrPickleball & tennis courtsbrState-of-the-art fitness centerbrMiles of walking & biking trailsbrScenic kayaking waterwaysbrClubhouse social activitiesbrThe Overlook Bar & Grill waterfront restaurantbrLocation ++brPerfectly situated only 4 miles from Downtown Naples and white-sand Gulf beaches, this property offers easy access to:br5th Avenue South dining & shoppingbrNaples beachesbrMarco IslandbrChampionship golf coursesbrWaterfront diningbrNature preserves & boating

2

Bed

2

Bath

6

Sleeps

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