Home Vacation Home Rentals By Owner In Naples, FL

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Exceptional(23)

$1338.92

/ Nightly
Private Vacation Home

2 Villas, Pickleball,Heated pool, Naples escape.

Naples, Florida, United States

Welcome to Naples Escape–The Estates, a Luxurious Retreat in the Heart of Naples.brSet on 2.5 acres of meticulously landscaped grounds, this estate offers both elegance and versatility with its beautifully designed main house and private guest house.brFeaturing a total of 6 bedrooms and 6 bathrooms, Naples Escape is the perfect destination for family gatherings, multi-generational reunions, getaways with kids, or groups of friends seeking the perfect balance of togetherness and privacy.brbrGuest can communicate with property manager through means of text/email/phone.brbrWebber Woods is a peaceful and quiet residential neighborhood in Naples, perfect for guests looking to relax and unwind. The area is known for its safety and friendly atmosphere, making it ideal for morning jogs, evening strolls, or simply enjoying the serene surroundings. With well-kept streets and a laid-back local vibe, it offers a wonderful balance of privacy and convenience — just a short drive to beaches, shopping, and dining, but tucked away enough to feel like your own private retreat.brbrThe entire estate is available to guest.brbrExceptional Featuresbr• Main House: The 4-bedroom, 4-bathroom main house includes two spacious master bedrooms, an open-concept design, and sophisticated interiors with high-end finishes.br• Guest House: A private haven with 2 bedrooms and 2 bathrooms, both master suites. Its stylish design makes it a perfect complement to the main house, offering added privacy while keeping your group connected.br• Fully-Stocked Kitchens: Both the main house and guest house feature fully-equipped kitchens, ideal for preparing family meals or hosting intimate gatherings.br• Modern Entertainment: Stay connected and entertained with high-speed internet, Wi-Fi, and Roku-enabled high-definition flat-screen TVs in every bedroom and common area.brbrAn Outdoor Sanctuarybr• Expansive Landscaping: The estate’s breathtaking grounds are divided into distinct sections in the front, middle, and back, each offering its own charm and tranquility. The lush greenery, vibrant gardens, and mature trees create a serene and picturesque escape.br• Hammocks Throughout: Unwind in one of the many hammocks tucked into peaceful corners of the property, perfect for reading, napping, or simply enjoying the calm surroundings.br• Heated Pool & Spa: The sparkling pool and relaxing hot tub provide the perfect spots to soak up the Florida sun or unwind in the evening.br• Gazebo with Barbecue: Dine al fresco under the shaded gazebo, complete with a barbecue grill for outdoor cooking and entertaining.br• Fire Pit: Gather around the fire pit in the garden for cozy evenings and meaningful conversations under the stars.br• Private Recreational Courts: The property features private pickleball and basketball courts, ensuring fun and activity for guests of all ages.br• Game Room: Have fun in the dedicated game room featuring a pool table, foosball, and air hockey—perfect for guests of all ages.brbrDesigned for Togetherness and PrivacybrNaples Escape is uniquely suited for groups seeking both connection and personal space. The guest house offers a quiet retreat, while the main house provides ample communal areas for everyone to gather. The thoughtful layout, combined with the expansive outdoor spaces, makes this estate perfect for multi-generational families, friend reunions, or working groups.brbrPrime Locationbr• 15 Minutes to the Beach: Easily access Naples’ renowned beaches, famous for their soft white sand and stunning sunsets.br• 30 Minutes to RSW Airport: Conveniently located for travelers, just a short drive from Southwest Florida International Airport.br• Close to Golf & More: Minutes away from world-class golf courses, grocery stores, restaurants, and boutique shopping.br• Convenience and Comfort: The estate’s prime location ensures you’re close to everything Naples has to offer, yet secluded enough to feel like a private oasis.brbrPerfect for Low-Key GatheringsbrThis estate provides the ideal setting for quiet celebrations, family reunions, and retreats. With exclusive use of the property and its tranquil surroundings, you’ll enjoy an experience of true relaxation and togetherness.brbrYour Private Paradise AwaitsbrWhether you’re lounging by the pool, streaming your favorite shows on high-definition TVs, relaxing in a hammock, or exploring the beautifully landscaped sections of the property, Naples Escape offers an unparalleled blend of privacy, comfort, and connection. Book your stay today and discover the beauty of this extraordinary estate!brbrOur home is conveniently located in a quiet residential area of Southwest Naples, offering easy access to everything you’ll need during your stay.brThe property is just a short drive from I-75, making travel to and from the area quick and convenient.brbrFor guests arriving by air, Southwest Florida International Airport (RSW) is approximately 30 minutes away by car, with a straightforward drive.brbrGrocery stores, shopping centers, restaurants, and pharmacies are all nearby and easily accessible within a short drive.brNaples’ famous white-sand beaches are typically 15–20 minutes away.brbrPopular destinations such as Mercato are about 15–20 minutes away, while Downtown Naples and 5th Avenue South can be reached in approximately 20-25 minutes by car, depending on traffic.brbrGolf enthusiasts will appreciate the location, with multiple public and private golf courses located nearby, many within a 10–15 minute drive.brbrWhether you’re heading to the beach, exploring downtown Naples, or running everyday errands, getting around from our location is easy and stress-free.brbrAll photos and people shown are genuine.
Bed 6

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Bath 6

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Sleep 14

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Exceptional(15)

$997.88

/ Nightly
Private Vacation Home

Luxe 2 King Ensuites. Salt Pool/Spa. Near beach, shops & food. NEW with 4 kings!

Naples, Florida, United States

SHORT VERSION:br- SOUTHERN FACING Saltwater Pool and overflow spa means more sun time than other properties!br- Lanai with high-end couches, outdoor TV, grill and refrigeratorbr- 1.7 miles (4 min drive, 7 min bike ride) to 2 renowned public beach access point and Ritz Carlton br- half mile to Trader Joe's (3 min)br- 1.1 miles to Mercato (shopping), Whole Foods, and top Naples restaurants (4 min)br- There are private golf cart shuttles companies in the neighborhood that will pick you up and drop you off anywhere in North Naples!br- Brand new build - 4 King Beds, 1 Queen, Full-sized Bunk Bed with Twin trundle roll-under bed, 1 full sofa air bed.br______________________________________________br(LONGER VERSION) - DETAILING THE SPACE:brWelcome to Palm Paradise Naples, a luxurious BRAND NEW BUILD with a coastal, serene inspired design. The home is unique due to its 2-story layout with 8 total beds + 1 sofa air mattress. Fast WiFi, bikes, yard games, pool turf, pool toys, 7 TVs, board games, chef's kitchen, and more!brbrUpon entering you will be greeted by tall ceilings, natural light, and designer furnishings that create an immediate sense of luxury and openness. This entire coastal retreat has a cohesive, bright, airy, yet warm feel and designed with designer furniture and furnishings.brbrWith a rare 6-bedroom floor plan for the area (with 2 being Ensuites), your family or guests are sure to love the bright open-concept living space but still have a private room to retire for the evening. The home's heated saltwater pool and overflowing spa (hot tub) is SOUTHERN FACING which basks the area with sun much longer than properties on the north side of the streets. Artificial turf surrounds the pool making it that much more comfortable to play the owner provided lawn games.brbrWith a luxury open-concept living and kitchen space, the property boasts a chef's kitchen with top-of-the-line appliances, quartz counter-tops, and a large island for both meal preparation and additional seating. With dining right off the kitchen and next to the 4-panel exterior slider, you are bathed in natural light with pool views creating a serene coastal vibe or a moody ambient night with the lit up pool and landscaping.brbrHigh-speed internet allows you and your guests to stream any movie or show on the 7 Smart TVs. Live/Cable TV is provided through YouTube TV. With plenty of classic board games, poker chips and playing cards, pool toys, beach toys, beach chairs and umbrella, 6 bicycles, coolers, adjustable bench with dumbbells, we strive to ensure you and your guests have everything possible to enjoy your close to the beach stay.brbrBEDROOMS LAYOUT:brMain Floor: br-- 1 King Ensuite (with Helix Midnight Luxe king mattress) br-- 1 King front bedroom (Helix hybrid king mattress)br-- 1 Full mattress-sized bunk bed with 1 twin trundle bedbr**Living room couch has a full-sized air-filled mattressbrUpstairs:br-- 1 King Ensuite (with Helix Midnight Luxe king mattress) br-- 1 King middle bedroom (Dreamcloud memory foam king mattress)br-- 1 Queen left bedroom (Dreamcloud hybrid queen mattress)brbrEnjoy provided coffee or your morning news/relaxation on the covered lanai or front entry seating. The outdoor spaces have been carefully designed to provide you with all the beachy, coastal and luxury comforts. In the evenings, gather around the heated, saltwater pool or spa under the starlit sky which is sure to make lasting memories.brbrWhether it's biking or strolling along the nearby sandy beaches, embarking on water sports, or shopping/dining at the nearby Mercato, downtown Naples, or Bonita, this vacation home is sure to please.brbrWelcome again to Palm Paradise Naples!br____________________________________________brGUEST ACCESS: brGuests have access to the entire property. Self-check in via a smart lock. The booking person will be provided a unique code to use for the duration of their stay.br-----------------------------------------------------brPARKING: Driveway parking allows up to 4 cars and we also allow 1 in the garage. We do store amenities in the garage so only 1 car can fit in garage.br-----------------------------------------------------brAREA: brNaples Park offers a ton with so many local and top restaurants, massage parlors, shopping centers, grocery stores all within 1-2 miles. br- 30 min to RSW airportbr- 45 min to Sanibel Islandbr- 45 Marco Islandbr- 15-20 Min to 5th Ave downtown and Old Naples.br- 2-5 min to Mercato shopping, dining, grocerybr- 10 min to Bonita SpingsbrbrMercato dining & Shopping include: Whole Foods Market, Narrative Coffee Roasters, Sur La Table', Chipolte’, Nordstrom Rack, Blue Martini, Burn Cigar Bar, Cavo Lounge, Bravo Cucina, Seasons 52, The Pub Naples, AZN, Burntwood Tavern, Bar Tulia, The 239, Capital Grille, Rocco's Tacos & Tequila Bar, Silverspot Cinema, and more!brbr- Waterside Shops an open air mall on water - 4 miles - Featuring Saks Fifth Avenue, Nordstrom, Anthropologie, Gucci, Apple, Brooks Brothers, Louis Vuitton, J. Crew, Banana Republic, Vineyard Vines and tons more…brbrVenetian Village has another outdoor shopping experience.brbrDowntown Naples has both 5th Ave and Old Naples which is sure to please for shopping and dining and relaxation.brbrAlso Conveniently Located Nearby:br- Ritz Carlton Beach Resort br- Turtle Club Beach Resortbr- LaPlaya Beach ResortbrbrNearby Grocery: Whole Foods, Trader Joe's and Publix grocery stores are 3-5 min drive.brbrOther area notables/things to do:br- LA Fitnessbr- Pelican Bay Community Park – Tennis, Sports Fields, Kids Play Areabr- Sun-N-Fun Lagoon Waterparkbr- Naples Sightseeing Boat Tourbr- Naples Electric Moped or Segway Toursbr- Golisano Children’s Museumbr- Naples Zoo at Caribbean Gardensbr- Naples Botanical Gardenbr- Artis Naples - Home of The Baker Museum & the Naples Philharmonicbr- The Naples Players TheatrebrbrMorning Spots:br- Narrative Coffee Roastersbr- Fit & Fuel Cafe' br- Juicelation - Organic Raw Juice Barbr- The Patio Cafebr- First Watch Breakfast & Lunchbr- Dunkin' & Starbucks close bybrbrDining Out: Some of our favorites:br- Bicyclette Cook Shop - chef won Food Network's Chopped (for foodies)br- The Bohemian - Bonita, FL (foodies)br- Unidos - Latin inspriedbr- Turco Taco (2 locations) - fast-casual great tacosbr- Capital Grillebr- Seasons 52br- The Bay House Restaurant - seafoodbr- DaRuMa Japanese Steakhouse - hibachi br- The Crust Pizza - Midwest style tavern style pizzabr- Mister 01 pizza - New York style (great red sauce)br- Cooper's Hawk Winery & Restaurantbr- Zen Asian BBQbr- Bha Bha Persian Bistrobr- Ichi Togarashi - Asian, Thai, Ramenbr- Namba Ramen & Sushibr- Rumba Cuban Cafebr- El Basque - Bonitabr- Sail's Naples (Fine dining)brbrCocktailsbr- Chartreuse - Craft Cocktailsbr- Sidebar - cocktail barbr- Bicyclette Cookshop Barbr_________________________________________brOTHER THINGS TO NOTE:brIf you need anything extra, or find that something is not functioning properly (or missing), please message us ASAP!
Bed 6

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Bath 4

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Sleep 14

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Exceptional(46)

$229.16

/ Nightly
Private Vacation Home

COZY COASTAL COTTAGE, Boaters Paradise At Naples Bay, Pickleball, Spa, Free Wifi

Naples, Florida, United States

Built with love in 2018 and decorated dream house just a few meters from the Naples Bay. Here, no wish remains open. The kitchen is lovingly and generously equipped, garage and driveway are available as parking. The hot tub on the west-facing terrace is provided by arrangement.brbr A dream for every boat lover. At the end of the street there is a public dock where your own boat can be dropped into the water. Within a few minutes you are on the most beautiful beaches of Florida. brbrThe house is completely furnished in Florida style. It has three generous bedrooms, two bathrooms and a west-facing terrace.brThe minimum age for all tenants is 40 years.brbrWelcome to our 2019 newly completed Coastal Cottage holiday home! We offer all you need for your Florida retreat. Vaulted ceilings, high end living space, 3 bedrooms and two bathrooms with Florida sunshine. The split floor plan offers a king size bedroom and two queen size beds. The kitchen is fully equipped and wants to be loved by every chef. Sun bathing, refreshing, and relaxing right away. Our screened lanai with outdoor exposure set, chaise lounges, table for six and a parasol so you can start sun bathing, refreshing and relaxing right away. The use of the whirl pool is optional, please ask if you are interested. brOur brand new coastal cottage is located only two minutes from Naples bay. If you take a short walk down the road to the west, you will get to Bayview Park, where you can enjoy a breathtaking view of the Naples Bay. You will be surrounded by the beautiful scenery of small fishing boats passing by, bringing in their catch, and attracting them. Naples 'gorgeous sunsets. We like to bring our beach chairs to the Bay and spend some time watching the boats passing by, or enjoying one of Naples' gorgeous sunsets. Oftentimes, there are dolphins, pelicans, and other exotic animals to see.brbrIt takes only ten minutes by car to reach the beautiful beaches of Naples and there are plenty of parking spots and beach access points. Given that our Coastal Cottage is close to Downtown and Old Naples, you can easily spend your evenings going to the beautiful 5th Avenue or 3rd Street, where you can finish the day with a glass of wine, or maybe enjoy the fine dining experience at one of Naples' well-known restaurants.brbrRight next to the East Naples Community Park. It is known for hosting the annual US Open Pickleball Championships, which is similar to Tennis in the United States. The park also provides basketball hoops, or you can join one of the classes offered, such as Zumba, which we enjoy and recommend dearly.brbrAt Sugden Regional Park, right across the road from there, you can enjoy the view across Lake Avalon. You can try canoeing, go for a walk, or enjoy your food in one of the picnic areas.brbrCelebration Park: Well-chosen restaurants cater their specialties from food trucks, and often there is live music to make an evening entertaining. Celebration Park and other local hotspots can be found along Bayshore.brbrCoastal Cottage holiday home, sitting on the lanai and listening to the cricket singing Naples to sleep. We hope you have a pleasant stay and enjoy your time just as much as we always do! Enjoy.
Bed 3

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Bath 2

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Sleep 6

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Exceptional(54)

$416.25

/ Nightly
Private Vacation Home

Walk to Vanderbilt Beach! Private Heated Pool! Close to Mercato and Ritz Carlton

Naples, Florida, United States

Our house is located in the desirable 500 block of Naples Park and is an easy walk 10-12 minute walk to beautiful Vanderbilt beach and The Ritz Carlton. The house is very close to Mercato (restaurants/shopping), and everything Naples has to offer. It is a 3/2 heated pool home with a screened in lanai. Perfect for couples, families, solo travelers, business travelers, and furry small dogs. All linens and towels included. Fully stocked kitchen for entertaining. Cable/WiFi, beach items. Master bedroom has a king bed and attached full bath. The other 2 bedrooms have queen beds. Central AC and laundry area. Linens and towels recently updated. Kitchen well appointed. New dishwasher and garbage disposal recently added. Wifi/Internet/Surround Sound. 2 beach bikes in garage. Bike rentals close by - Downtown 5th Ave. less than 8 miles away. Beautiful beach a short walk with beach chairs and beach cart available in garage. Pool Service comes once a week to care for pool. Too many restaurants to list. Welcome notebook provided in house. Master bedroom has a king bed and private luxurious bathroom. Two other bedrooms have queen beds. Second bathroom beautifully remodeled. Kitchen has granite and stainless appliances. New dishes/glassware, etc. Screened in Lanai, beautiful heated pool and outdoor lounge chairs provided.
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Bath 2

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Sleep 6

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$338.11

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Private Vacation Home

Elegant Villa in Olde Naples | Steps to Dining, Shopping & Gulf Sunsets

Naples, Florida, United States

Welcome to your Naples escape—where luxury, location, and leisure come together in the most perfect way. This 3-bedroom, 3-bath villa places you right in the heart of Olde Naples, just a short stroll from the sugar-white Gulf beaches, vibrant 5th Avenue South, and charming 3rd Street South. From morning coffee on the balcony to sunset walks on the beach, every day here feels like a getaway dream.brbrSpread across three levels with a private elevator for easy access, this villa was designed for both style and comfort. The master suite features a king-sized bed, spa-like en-suite bath, and private balcony for quiet morning moments. A second bedroom with a queen bed offers its own retreat, while the third bedroom with a twin Murphy bed is perfect for extra guests or a cozy reading nook. With six balconies, natural light pours in from every direction, creating breezy, sunlit spaces you'll love to unwind in.brbrAfter a day of beachside adventures, rinse off in the outdoor shower before gathering on the covered courtyard patio for cocktails and casual dinners, surrounded by warm Naples breezes. An oversized two-car garage with an EV charger, plus additional guest parking, means every detail is taken care of for your stay.brbrWhether you're sipping wine under the stars, exploring world-class restaurants just steps away, or simply embracing the Naples lifestyle, this villa is your ticket to an unforgettable vacation.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 for February and March.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.
Bed 3

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Bath 3

Bath

Sleep 5

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Exceptional(3)

$273.06

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Private Vacation Home

Naples Resort-Heated Pool-Near Beaches-Game Room

Naples, Florida, United States

Welcome to SALT + LIGHT! Family owned + updated with new porcelain tile, stainless appliances, quartz countertops, + new A/C!brbrA+ Location:br3 mi-Downtownbr3 mi-Tin Citybr4 mi-Beachbr5 mi-Naples Zoobr5 mi-Botanical Gardenbr5 mi-Great Wolf LodgebrbrHighlights:brPrivate Heated Pool (no extra charges)brCovered Lanai w/String LightsbrFire PitbrGame RoombrBeachy Wall MuralbrOutdoor ShowerbrLaundry RoombrWorkspacebrBunk BedsbrTVs in all bedroomsbrMedical-Grade Air PurifierbrDriveway ParkingbrGym, Pickleball + SaunabrbrThe spacebrLocated in the heart of Naples, this beautifully updated and well maintained pool home is the perfect place for your vacation. A complete renovation of the kitchen and all bathrooms, freshly painted interior, newer roof, brand new AC and water heater. The bright open floor plan features large windows throughout and volume ceilings. Lots of closets and storage and a large master bathroom add to this home's standout features. A recent pool resurfacing and expansive lanai has transformed the private pool area into a backyard oasis perfect for relaxation. Enjoy the community clubhouse with a pool, tennis courts, sauna and fitness room surrounded by a 3 mile greenway for walking/biking.brbrClose to Everything You Love: This exceptional single family property offers the ultimate in privacy and luxury, yet remains conveniently located just minutes from the best that Naples has to offer. Enjoy easy access to world-class shopping, dining, and the renowned Fifth Avenue. The pristine beaches of Naples are just a short drive away, and with proximity to I-75, you’ll have quick access to all of Southwest Florida’s attractions. Located on a quiet curved street with a landscaped island, offering low through-traffic and a cul-de-sac feel.brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bed with 65 inch smart TV and cablebrPrimary suite with an open-concept layout where the bedroom flows seamlessly into the spa-style bathroombr- Bedroom 2: 1 queen bed with 55 inch smart TVbr- Bedroom 3: 1 full + twin bunk bed with smart TVbrbrRESORT-STYLE AMENITIESbr- Outdoor pool (open year-round, heated in winter)br- Fishing pondbr- Clubhouse + gymbr- Tennis & pickleball courtsbr- Walking trailsbrbrINDOOR LIVINGbr- Family room with 75 inch smart TV and cablebr- Dining area features a coastal inspired wall mural that brings a relaxed beach feel indoorsbr- Game room with Pac-Man + Simpsons arcade (also includes many retro games) + classic board and card gamesbr- Open kitchen/living spacebr- 2 showers and jacuzzi tubbr- over 2,000 sq ftbrbrOUTDOOR LIVINGbr- Oversized private Lanai w/ 65 inch Smart TV & furnishings offering a stunning setting for outdoor livingbr- automatic Fire Pitbr- Outdoor showerbr- Beach gear providedbr- Covered entryway patiobrbrKITCHENbr- Large island with quartz countertops + breakfast bar seatingbr- New Refrigerator, stove/oven, dishwasherbr- Coffee maker, microwave, blender, toasterbr- Cooking essentials, dishware & flatwarebrbrGENERALbr- Free WiFibrModem and router are neatly tucked away in the laundry room and garage for a clutter-free living spacebr-Charging station for all of your devicesbr- Central A/C + ALL NEW ceiling fans with remotesbr- Towels & linens, complimentary toiletries, hair dryerbr- Indoor laundry room with Samsung washer & dryerbr- Keyless entrybrbrACCESSIBILITYbr- Single-story home, step-free accessbrbrPARKINGbr- Drivewaybr- No overnight street parking (per HOA)brbrGUEST ACCESSbrGuests will have access to the entire property via keyless entrybrbrOTHER THINGS TO NOTEbr- No smoking or vapingbr- No petsbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Photo ID may be required upon check-inbr- While the home does not have a BBQ grill due to safety policies, you’ll find many amazing restaurants, seafood spots, and outdoor dining options nearby.brbrADDITIONAL INFORMATIONbr- Crown Pointe HOA requires guests to complete application for their stay. (Details available upon booking.).br- Your safety matters. This home features 2 exterior security cameras on the front and back of the house. The cameras do not look into any interior spaces.
Bed 3

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Bath 2

Bath

Sleep 6

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