Home Vacation Home Rentals By Owner In Cudjoe Key, FL

Showing 40 Of 199 Vacation Rentals
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Exceptional(16)

$391.56

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Private Vacation Home

Moana Hale Paradise #164 at Venture Out in Cudjoe Key

Cudjoe Key, Florida, United States

Welcome to Moana Hale Paradise #164 at Venture Out in Cudjoe Key! This ocean-view canal-front midrise house is a perfect spot for couples or up to a family of six. The home is located near the canal entrance and protected in a 60 ft wide canal. Access to the Gulf to Mexico or the Atlantic is a breeze. Step onto the porch for breathtaking sunrise views, then head inside to discover a well-equipped kitchen that s seriously decked out - we are talking Keurig, Air Fryer, Ninja Blender, rice cooker, and more! Pull up a bar chair at the kitchen island, or kick back in the living room for some board games, or challenge others to a game of starfish and seashell tic-tac-toe. The couch also pulls out into a Queen sleeper sofa.brThe master bedroom has a Queen bed and boasts an ensuite bathroom . There is also a desk for work or makeup sessions in this bedroom.brThe guest bedroom has a Queen bed and the Guest bathroom is just a skip away.brForget packing shampoo and soap - we've got you covered!brThere are TVs in each room to satisfy all guests and family member s choices.brOutside, there's a 35' dock which can accommodate up to a 32' boat, 16' boat whips, mooring balls, tie downs, a fish cleaning station, hoses to clean your boat, and a dock ladder to help get in out of the canal after you kayak or paddleboard.brGrab one of the 4 bicycles from under the house for a park ride or a spin down the bike trail. There s a beach cart to take your supplies to the pool or fishing areas.brThe downstairs storage room also has a BBQ gas grill, a bait freezer, and lots of storage for your gear. Please note: the bait freezer will need to be plugged in upon arrival.brVenture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts.brAdventure beyond the gates for a bite to eat at some of Florida Key's favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away!brWhether you re a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key.brSorry, no pets allowed at this home.brLocated inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 22.5' L x 12'W. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay.brMain guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance.brTo ensure that you are protected, as well as the owner, we offer a $55 Damage Waiver Insurance. If you chose to opt out of the Damage Waiver a refundable $1,500 Security Deposit will be collected. Main guest must email a copy of your driver's license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee. brSocial Media - br@bluescaperealestatebrYouTube Videos @bluescapevacationsbrBook your stay today and experience the beauty of waterfront living!
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Exceptional(2)

$518.81

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Private Vacation Home

Sea La Vie - Your Oceanfront Escape - 3BD/3Bath - Cudjoe Key

Cudjoe Key, Florida, United States

Sea La Vie: Oceanfront Vacation Rental in Cudjoe Key, FloridabrbrLooking for the perfect oceanfront getaway in the Florida Keys brWelcome to Sea La Vie, a 3-bedroom, 3-bathroom elevated home in Cudjoe Key, offering stunning Atlantic Ocean views, modern amenities, and a relaxing atmosphere. brbrPlease note: A 29 night minimum stay is required due to local ordinances.brbrWhy Choose Sea La Vie br* Prime Location: Nestled in the serene Cudjoe Bay, steps from crystal-clear waters and endless ocean adventures.br* Spacious Layout: Features 3 bedrooms and 3 bathrooms, including a master suite with a king-size bed and en suite bathroom.br* Open-Concept Design: Bright, airy living space with ocean views and a fully equipped kitchen for easy meal prep.brbrOutdoor Highlightsbr* Screened Veranda: Perfect for morning coffee, sunset dinners, or simply enjoying the sea breeze.br* Dock Access: Swim, fish, or dock your boat (up to 40 feet with in-water docking).br* Relaxation Spaces: Lounge in the hammock, grill your fresh catch, or stargaze after a day of adventure.brbrKey Amenitiesbr* High-speed WiFi to stay connected.br* Linens and essentials provided for a hassle-free stay.br* Dedicated parking space with additional trailer parking in the large front yard.br* Fully equipped kitchen with counter seating and a cozy dining area.brbrPerfect for Extended StaysbrSea La Vie is designed for month-long rentals, making it ideal for extended vacations in the Florida Keys. Whether you’re boating, fishing, or simply unwinding, this home offers the perfect blend of comfort and adventure.brbrBook Your Stay Today!brEscape to Sea La Vie and experience oceanfront living at its finest. Secure your dates now and start planning your dream vacation!brbrImportant Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check.
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Bath 3

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$332.04

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Private Vacation Home

Lime in the coconut

Cudjoe Key, Florida, United States

You put the LIME IN THE COCONUT and add a little fun! Great times to be had in this very nice 3 bedroom 2 bath custom home located on the ocean side of Cudjoe Key. The home is beautifully decorated with deep colors and teak floors, giving a very tropical feel. The kitchen is modern and has everything for your cooking needs, including a built-in eating bar. The living room is comfortable with premium leather seating and features a large flat-screen TV. The master bedroom has a king bed, the second bedroom features a queen bed and the third has a pair of full-sized beds. From the living room, there is access to the huge deck/porch area for relaxing in the sun or shade. Amenities include 2 TVs, central A/C, wireless Internet, gas barbecue and anything else you may need. Outside there is a full-length concrete dock with excellent boating access to the Atlantic and coral reefs for snorkeling and diving or Gulfstream for fishing. You might choose the backcountry and Gulf for fishing or exploring as an option. There is also a large open backyard area with tropical plantings. The world-class beach at Bahia Honda State Park is about 20 minutes north by auto. Nearby you will find groceries, fuel, marinas, boat rentals, post office banks, restaurants, and much more. Unique Key West and all it offers is 23 miles south. The international airport in Miami is about a 3-hour drive. THIS HOME IS A 28-DAY MINIMUM RENTAL PER MONROE COUNTY CODE.
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Exceptional(108)

$457.32

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Private Vacation Home

SAVE BIG $$$ JUNE!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key, Florida, United States

ALL NEW RENOVATIONS COMPLETED JUST FOR YOU!brA perfect oasis with beautiful views all day, every day. Come enjoy your time with your choice of a tranquil pool, relaxing hot tub, or a refreshing dip in the Atlantic. A short drive to Key West means you are close to all the action but far enough away to enjoy your own private piece of paradise. Fill your days with everything from fishing to tennis and your nights with beautiful sunsets and long-lasting memories. The Keys are calling, are you ready to answer brbrMagnificent newly renovated 2 bedroom 2 bathroom cottage with 35 ft of seawall in Cudjoe Key. Located in the lower Florida Keys at MM#23 only 20 minutes to Key West. Our cottage is in the gated community of Venture Out.brbr*Sleeps up to 6:brMaster bedroom with king bed and en-suite br2nd bedroom with queen bedbr*Living room with queen sleeper sofabr*2 full Bathrooms. One with shower/tub combination, the other with showerbr*Living room with 55 flat screen LED TV and DVD Player.br*Central A/C & Heatbr*New kitchen appliance package in stainless steelbr*New tinted windows & sliding doorsbr*Fully equipped kitchen with stove/oven, refrigerator/ freezer with ice maker, toaster oven, microwave, dishwasher, blender and pantrybr*Both Keurig and 12 cup Mr. Coffee makerbr*Seating for sixbr*New extra large washer & dryerbr* New outdoor propane grillbr*35-foot concrete seawall with swim ladder and fish filet station.br*Covered porch with table and chairs overlooking the canalbr*BRAND NEW BICYCLES FOR 4!br* 2 Brand New two-seater kayaks! Universal life vests includedbr*HIGH SPEED Wi-Fibr* Keyless entry so you have no worries about losing keys!br*All new furniture and the comforts of homebr**VENTURE OUT AMENITIES SUCH AS:brHeated Pool, Hot Tub, Basketball Courts, Pickleball Courts, Marina with fuel, 2 Boat Ramps, Private Convenience Store, Children's Pool, Bath Houses, Laundry Facilities, Fish Cleaning Station, Horseshoes, Ping Pong, Children's Play Area, Bocce Ball, 24 Hour Gated Security, Salt Water Swimming Area, Recreation Hall with Free WIFI, Library, Pool Tables, Table Tennis, and Board Games. Sunday church services. Weekly activities for everyone in the community to enjoy! br*One car is allowed to park in the driveway.for free.br**Overflow parking for 1 extra car, 1 boat trailer for an additional fee for 14 days max. OVERFLOW PARKING IS ON A FIRST COME FIRST SERVED BASIS & IS NOT GUARANTEED. br*Maximum occupancy 6 guests - strictly enforced. br***ONE TIME ENTRANCE FEE $125. PAID UPON ARRIVAL AT GUARD BOOTH. (credit cards or cash accepted).br*ALWAYS SMOKE AND PET FREE brThere are 2 outdoor cameras. 1 facing the driveway and 1 facing the dock.
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Bath 2

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$354.54

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Private Vacation Home

Spectacular Sunsets, 3 bed, 2 bath with pool

Cudjoe Key, Florida, United States

Escape completely in this open and airy 3 bedroom 2 bath oceanfront pool home. Situated on the northern shore of Sarcarma Bay on Cudjoe Key, this home offers tropical living and real southern exposure. The living area, the modern kitchen, and the master suite all open onto a full-length screened and covered porch overlooking the water. The house is fully equipped for your every need, and there are 2 king beds and 2 twin beds for your convenience. Two large-screen smart TVs, broadband internet, and barbecue grill, and a downstairs weight room with boxing bags are just a few of the extras. For the boater or fisherman, there is excellent access from the wood pier/dock to the coral reefs of the Atlantic, the backcountry, and the Gulf. The world-class diving and snorkeling at Looe Key Reef National Marine Sanctuary is just offshore. There are also 4 Canoes and bikes for your use. To the north by auto, the beautiful beach at Bahia Honda State Park is within a 20-minute drive. Nearby you will find most needed items with groceries, fuel, banks, post office, and many other stores. Key West with its history, unique shopping, and fine dining/nightlife is 23 miles to the south. The Miami International Airport is about 3 hours away. This is a designated NON-SMOKING home. Ask about our pet policies. THIS HOME IS A 28-DAY MINIMUM RENTAL PER MONROE COUNTY CODE. br
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$481.87

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Private Vacation Home

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Cudjoe Key, Florida, United States

Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water views. Located on the open water, with a 52' concrete dock/seawall complete with dock posts, swim ladder. Beautiful views of the open water from the living room, dining room and kitchen.- perfect location for your boat or you can rent one nearby.This is a fully furnished 2 bedroom/2 bath stilt home with parking and covered living space below. The master bedroom has a king sized bed, the second bedroom has a queen bed, gorgeous ocean views, second-floor deck, direct access to the Atlantic and the Gulf. Central A/C and heat, overhead ceiling fans, full kitchen with microwave, full sized washer/dryer, 42' high def flat screened TV, Wi-Fi, cable,ceiling fans, linens, dishes, glasses and wine glasses etc Recreation center with darts, and ping pong. Post Office and a Library 24 Hour Gated Security. Gated private community with 80 foot heated shared pool, large kiddie pool, salt water swimming area, marina, convenience market, small post office, 2 lighted tennis court, basketball, bocce courts, ping pong, and two large boat ramps, marina, ship's store. Our very cute little low key fishing community is friendly and has little houses as well as some campers. brLocated just 15 minutes to either Key West to the west or Bahia Honda State Park (voted one of the top 10 beaches in the U.S.) to the east, a water-lover's dream. This 69 acre resort was created to put the ocean at your back door. Amenities: Central Air Conditioning/Heating, 42'HD TV, Full Kitchen, Microwave, Dishwasher, Refrigerator, Ice Maker, Cooking utensils, Linens provided, Washer, Dryer and Gas Grill (BBQ) Community - 80 foot heated pool, 2 lighted tennis courts, bocce courts, basketball, ping pong, full service marina, boat ramps, salt water swimming area, small playground. Activities: Swimming, boating, skiing, sailing, biking, fishing, tennis, bocci, ping pong, basketball, scuba diving, parasailing, airplane rides, golf in Key West, snorkeling Looe Key. Area: We are located on accessible deep water boating channels to both the beautiful back country (bayside)as well as a quick ten-minute run to the open Atlantic (oceanside) and it's Coral Reefs. Looe Key National Marine Sanctuary is a nearby must for snorkeling and diving in the crystal blue Atlantic. On the gulf side, Cudjoe Key offers the Great White Heron National Wildlife Refuge...A kayak or small boaters paradise.brFor Divers and Fisherman: The retired 523 foot WWII U.S. missile tracking ship Gen. Hoyt S. Vandenberg that once tracked space launches off Cape Canaveral, and also monitored Soviet missile launches during the Cold War, has been intentionally sunkoff Key West in late May to become an artificial reef in the Florida Keys National Marine Sanctuary. Trip Interruption/Cancellation Insurance is paramount to protect yourselves from all manner of life's situations including hurricanes, death, loss of job, illness etc etc. Make absolutely sure you take it out. Venture Out charges a fee of $125.00 due at check in, payable to Venture Out, this is for use of the amenities. Parking for one car, one golf cart and one motorcycle, additional vehicles will park in overflow parking. If you are bringing a boat, we have trailer storage for you just down the street. Please let me know.
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Bath 2

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Sleep 6

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Exceptional(7)

$223.45

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Private Vacation Home

Nice home on Atlantic side of Cudjoe Key!

Cudjoe Key, Florida, United States

This home would be the perfect vacation spot for a small family or a group of friends. There are plenty of fun restaurants, tiki bars and even the southern most point of the United States, within a short drive from our home. Bring your own kayaks or motor boat for some fun in the water (this home has a sea wall that you can dock at, but you must bring your own bumpers and mooring)brbrThere are 3 beds and a sleeper sofa in the Livingroom to accommodate 6 guests. There is an outdoor shower by the picnic table and an another restroom in the garage.brbrNo Parties or eventsbrNeighbors value the serenity of a quiet neighborhood. Please follow all Parking, pet restrictions and property boundaries as well as monitor occupancy and noise levels to ensure consistency.br **Do not set the temps below 70 degrees. This will cause the ac to freeze up as they will not be able to cycle on and off. In Florida weather all ac’s can only cool so far with doors constantly being open and closed.**br• Smoking is strictly prohibited inside the home including vaping of any kind and the use of medical marijuana. If smoking outside, please dispose of butts in appropriate containers and do not litter gardens or the yards.br• Garbage and recycling Day is Monday and Thursday. Please place garbage containers curbside on Wednesday night.br• The Sewage System of our home will be damaged if products other than toilet paper are flushed. The following are a few examples of items that cannot be flushed: diapers, bones, sanitary products, coffee grounds, band aids and dental floss.brTV is Wi-Fi streaming only using apps such as Netflix. Please bring your log in information for those apps as you will need them. There is no cable. It is a Roku device which does have the Roku channel for some free tv.br Quiet time is from 9 pm until 7am. Visitors who remain in the home after 9 pm will be considered extra guests and you will be charged as such. Visitors are any persons not listed in the reservation. br• We allow up to 2 pets for an additional fee of $150.00. You can add a third animal for another $50 fee. Our homes will only accommodate up to 3 pets, per reservation. If pets are brought in without our knowledge then a $500 daily fee will be applied or result in immediate eviction with no refunds for remainder of your stay. Please keep pets on leash and please clean up after your pet and dispose of pet waste properly.br• The Barbeque grill has propane. Please clean and turn off tank after each use. br• Please wear shoes at all times when walking on shells in side yard as they are sharp and can cut your feet.br• Please note that Lawn maintenance will be done between the hrs of 7am and Sunset dependent on weather any day of the week. brDisclaimer: there is a security camera at the top of the stairs and the back porch ceiling which are also the porch lights and will be running during your entire stay and result in a fee or immediate eviction if turned off.br To help prevent the spread of Covid-19, we have enhanced our cleaning procedures by blocking off 24 hours before and after a guest has stayed in the home. br PLEASE NOTE: we cannot offer refunds for issues related to insects or weather conditions including but not limited to no wifi, power outages or issues out of our control. Our property is located in a natural environment where insects and changing weather are part of the experience. We appreciate your understanding and hope you enjoy your stay. br No Electric vehicle charging. Please google and use nearest chargers.br**** Owner or manager may stop by ANYTIME to verify number of guests Or maintain Property****brbr• Check out is 10am.
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Bath 1

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Sleep 6

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$386.52

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Private Vacation Home

JUNE & JULY SPECIAL! 3 Bedroom/2 Bath Canal Home w/ Private Pool in Cudjoe Key

Cudjoe Key, Florida, United States

Welcome to Reel Life, a beautiful Cudjoe Gardens oasis! Located on the ocean side of Cudjoe Key, this home has everything you need to enjoy a true Florida Keys vacation! It features an in-ground heated pool, a large Tiki hut/bar for hanging out by the pool, an expansive dock to accommodate your boat, a sandy beach area overlooking the canal, a screened lanai and a top of the line outdoor kitchen...and it's all located on a deep, wide, clear, flow-through canal with no bridges to the open ocean! It's truly an outdoor oasis and a boater's dream! Spend the afternoon out on the boat and/or exploring the canals with your snorkel gear then cook up your fresh catch and hang pool-side for the evening! Cudjoe Marina is right around the corner with a ramp and fuel and you are only 30 minutes to Key West or 15 minutes to Big Pine for all your shopping and conveniences.brbrThe home itself is ground-level and is super spacious with an open floor plan, 3 bedrooms that sleeps 6 adults, a bonus room with bunks for kids, 2 bathrooms, a large updated kitchen, separate dining and plenty of essentials. It's clean, comfortable and fully equipped with everything you need to enjoy your vacation!brbrCome stay at your very own tropical paradise!brbr*For a complete viewing of this home, check out the posted video*brbr***PETS ALLOWED BY APPROVAL ONLY***brbrPLEASE NOTE: This is a monthly rental. During season (Winter and Summer), we only rent full months at a time, ie. all of January, all of February, all of March. We do not split months, ie. Jan 15 - Feb 15.brbrbrNOTE: All images used are for illustrative purposes only. Individual features such as bed sizes/configuration, bedding, décor, appliances, colors, extra amenities, etc. may vary since these are private homes and owners redecorate often. Please also note that pictures are taken in different light conditions and computer screens have different individual settings that moderate colors. Please read the written description and ask questions if you have any specific needs and/or concerns. All furnishings and décor are subject to change at any time.
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Exceptional(8)

$334.57

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Private Vacation Home

Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West

Cudjoe Key, Florida, United States

Relax! Swim! Boat! Bike! Kayak! Hike! Pickle Ball, yes even that. Just a short distance to Key West with quick and easy access to the Gulf or open water, a perfect location for family chill days, fishing & boating. Spacious living areas with 3 oversized bedrooms and 2 full bathrooms. Store your boat on site or tie up to the dock. Beautiful pool, tiki hut, bikes, kayaks, pickle ball court, grill, fruit trees and even a hiking trail across the street to keep everyone happy and entertained.brbrWinter, work or just typical life got you stressed and wore out. Well come rejuvenate at Lobster Nirvana! brWelcome to our dream! A large lot with grass in the Keys Yes and totally fenced to sprawl out with the privacy your looking for. The first eye catcher is the refreshing pool the kids will actually have room to play in and the tiki bar right there so you can relax poolside. 150' dock so you have plenty of room to tie up a boat or two. Dock has a step down area with a ladder for easy in and out, also has a fish cleaning station. Throughout the yard there are several fruit trees, star fruit, mangos, and avocados. There are several patios and decks to hang out on. Sit out back and look over the canal or out front and watch the sunrise or sit in the screened in deck, sip coffee while you gaze at the canal (my favorite morning spot).brUpstairs you have an open kitchen, dining and living room. All of the bedrooms are spacious, one has a king size bed and workspace in case you need to take care of some business. All of the bedrooms are spacious. One has a king size bed and a workspace in case you need to get some work done. The other has a queen bed. The master bedroom is huge and has a king bed with on suite. Everything you need to relax and recharge. All this with some interesting lobster house history, if you stay you'll learn the insights of the past for the Lobster Nirvana
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$368.54

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2 Bedroom Canal Home in Cudjoe Key, FL w/ Private Pool & Extra Loft Space

Cudjoe Key, Florida, United States

Welcome to Gecko House! This canal-front 2 bedroom, 2 bath house is located in a great boating area with easy access to the ocean. It has a beautiful pool area under the house with seating for cocktail hour and a deck for viewing the sunrise while you sip your morning coffee.brbrThis home has a two bedrooms, one with a King size bed with an en-suite bathroom with a full size tub and shower. The second bedroom has a Queen bed. The second bathroom has a walk-in shower. There is a loft with a futon.brbrThe living room has lots of comfy seating to relax and watch the flat screen TV.brbrOutside under the house is a table with 4 chairs and a swing to relax in the shade while sipping your favorite cocktail. In the morning, you can sit on the deck upstairs drinking your coffee while watching the sun rise.brbrThere are two kayaks for your use and of course a concrete dock for your boat.brbrEnjoy all the unlimited water activities like swimming, fishing, and diving the Keys has to offer. Discover an assortment of Florida Keys wildlife. Big Pine Key is located a few miles up where you’ll find a shopping plaza hosting Winn-Dixie, Artists in Paradise, Beall’s Outlet, Radio Shack and branch of the Monroe County Library with Wi-Fi internet access.brbrTake a trip down to Key West for the daily sunset celebration or a romantic sunset cruise. Or visit one of the many venues offering the finest in live entertainment and great food. Be sure to take a stroll up and down Duval Street and visit the art galleries, shops, and more! Take the family for a sunset cruise or go snorkeling, kayaking, or whatever water sport the beautiful Florida Keys has to offer.brbr***PETS ALLOWED BY APPROVAL ONLY***brbrNOTE: All images used are for illustrative purposes only. Individual features such as bed sizes/configuration, bedding, décor, appliances, colors, extra amenities, etc. may vary since these are private homes and owners redecorate often. Please also note that pictures are taken in different light conditions and computer screens have different individual settings that moderate colors. Please read the written description and ask questions if you have any specific needs and/or concerns. All furnishings and décor are subject to change at any time.
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$268.84

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Private Vacation Home

Island Home in Paradise #624 - OCEANFRONT Community!

Cudjoe Key, Florida, United States

Island Cottage Retreat in Venture Out - Pet-Friendly 2BR, Lots of Amenities & Private PatiobrWelcome to Island Home in Paradise #624, a charming 2-bedroom, 1-bath vacation retreat located inside the private, gated community of Venture Out on Cudjoe Key in the beautiful Lower Florida Keys. Tucked away on a peaceful lot with tropical landscaping and multiple outdoor living spaces, this cozy island getaway is perfect for couples, small families, remote workers, or anyone looking to relax and experience true Keys living.brThe SpacebrIsland Home in Paradise #624 offers a comfortable and inviting layout designed for easy vacation living. Inside, you'll find a bright living area with comfortable seating, smart coastal décor, and a dedicated desk workspace for guests needing to work remotely during their stay.brThe fully equipped kitchen makes it easy to prepare meals at home and includes everything needed for cooking and dining in. Enjoy your morning coffee with the Black & Decker 12-cup drip coffee maker before heading out for a day on the water.brCentral A/C and Wi-Fi are provided throughout the home for added comfort and convenience.brBedrooms & Sleeping ArrangementsbrPrimary Bedroom: Queen-size bed with cozy bedding and ample storagebrGuest Bedroom: Queen-size bed with comfortable furnishingsbrMaximum Occupancy: 4 GuestsbrBathroombrFull bathroom with walk-in showerbrOutdoor LivingbrOne of the highlights of this home is the private outdoor space. Guests can enjoy two separate patios designed for relaxing and entertaining.brThe rear patio offers a peaceful and secluded setting surrounded by tropical landscaping, perfect for morning coffee, reading, or unwinding after a day exploring the Keys.brThe front patio is tucked beside lush palms and includes outdoor seating and a barbecue grill, creating the ideal space for outdoor dining and enjoying warm island evenings.brPet-Friendly DetailsbrThis property is pet-friendly for up to 1 dog with a maximum weight of 25 pounds. A paid pet fee of $250 applies. Guests must notify the rental manager at the time of booking if bringing a pet.brCommunity Amenities at Venture OutbrVenture Out is one of the most popular waterfront communities in the Lower Florida Keys and offers guests access to outstanding amenities including:br80' heated saltwater swimming pool, hot tub, kiddie pool, and saltwater swimming lagoonbrMarina store with fuel, bait, and convenience itemsbrBoat ramp and boat wash-down stationbrLighted tennis courts, pickleball, basketball, bocce courts, and playgroundbrPost office and community common areasbrGated security and electric golf cart-friendly streets throughout the communitybrLocationbrConveniently located on Cudjoe Key, you'll be just minutes from some of the Lower Keys' favorite restaurants and attractions including Square Grouper, The Bent Prop, Morning Joint, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House & Miniature Golf.brThe home is also located near the world-famous Looe Key Reef, known for exceptional snorkeling, diving, and fishing opportunities.brFor additional dining, nightlife, shopping, and entertainment, Key West is only about 25 minutes away.brGood to KnowbrVenture Out registration fee: $125 (subject to change), paid directly to the community at arrival (cash or credit card; processing fees may apply)brParking: 1 vehicle only. The driveway measures approximately 18' long x 13' wide and vehicles must fit fully within the driveway without extending into the roadwaybrOverflow parking may be available through Venture Out for an additional daily fee depending on availabilitybrQuiet hours: 10:00 PM to 6:00 AMbrStarter supplies provided: A starter supply of essentials is included to get you started. These supplies are generally enough for a 1-night staybrWi-Fi provided throughout the homebrPrimary guest must be 25 years of age or olderbrPayment & Booking RequirementsbrSigned rental agreement and government-issued ID are required after booking. Please reply to the email you receive from us after signing your rental agreement with a photo of your ID.brA 4% credit card processing fee applies to credit card payments.brWhether you're spending your days boating, fishing, snorkeling, relaxing poolside, or simply soaking in the laid-back atmosphere of the Florida Keys, Island Home in Paradise #624 offers the perfect tropical escape in one of the Keys' most amenity-rich waterfront communities.
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Exceptional(8)

$686.28

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Private Vacation Home

Oceanfront w/stunning open water views and private seawall! 30 mins to Key West!

Cudjoe Key, Florida, United States

Oceanfront with stunning open water views and deep water access! Oceanview Serenity offers stunning Atlantic views, and a private seawall for your boat. Kayaks, paddle boards, and more. This renovated 2BR cottage sleeps 4 with one King and one Queen size bedrooms, and one with an ensuite bathroom. Both bedrooms are equipped with JW Marriott mattresses for your ultimate comfort and relaxation. ALL new appliances! Enjoy resort amenities like a pool, hot tub, tennis, pickle ball, and marina store. Just 30 minutes from Duval Street, Key West. $125 resort fee due at check-in (per stay). One (1) parking spot. brbrWe can't wait to host you at this beautiful oceanfront cottage!brbrThe spacebrOceanview Serenity – True Oceanfront Cottage with open water views!brWake Up to Endless Atlantic Views – Just 30 Minutes from Key West!brbrAbout this spacebrUnlike canal-front properties, Oceanview Serenity sits directly on the Atlantic Ocean, offering stunning, uninterrupted water views and a true seaside experience. Located in the secure, amenity-rich Venture Out Resort, this recently renovated 2-bedroom cottage includes a private seawall, perfect for boating enthusiasts. Enjoy complimentary kayak/paddle boards and many board games, and more! Relax knowing you're only 30 minutes from the heart of Old Town Key West and the world famous Duval Street!brbrThe SpacebrWatch the sun rise over the ocean from your living room in this beautifully updated cottage with an open floor plan and expansive ocean views. Perfect for families or groups, the home comfortably sleeps up to 4 guests.brbrStep outside and launch your kayak or paddle board directly from the seawall. Explore the nearby Venture and Out Keys or lounge in the ocean with provided floats and life jackets.brbrAdditional Amenities Include:brbr* Washer & dryer in the unit (plus coin laundry nearby)br* Access to resort amenities: pool, hot tub, tennis & pickleball courts, playground, picnic areas, boat ramp, and marina store with fuel, groceries, and tacklebr* 24/7 gated security for peace of mindbrbr**Please Note**brUpon arrival, Venture Out Resort collects a *one-time* mandatory $125 resort fee (per stay, not per night), which includes full access to all resort amenities and a parking permit. Overflow parking is available for boats, trailers, or additional vehicles for a nightly fee.brbr**Guest Access**brGuests have full private access to the entire cottage, private seawall, and all the resort amenities.
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$149.41

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Private Vacation Home

Canal-Front Gem w/ Peekaboo Views in Cudjoe Key!

Cudjoe Key, Florida, United States

Spectacular Sunsets & Bay View | Waterfront Lounge Area | 2 Kayaks brbrPlanning a long-term stay in the Florida Keys Book this 2-bedroom, 2-bath Cudjoe Key vacation rental! Enjoy slow mornings with coffee on the spacious deck, then take the provided kayaks out for a spin or beachcomb at Bahia Honda State Park. Later, gather around the fire pit and savor the sunset. No matter who you’re traveling with, this home offers the perfect base for a memorable month in the Sunshine State!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Living Room: 1 queen sleeper sofabr- Additional Sleeping: 1 queen air mattressbrbrOUTDOOR LIVINGbr- Bay & sunset viewsbr- Deck w/ seating & Smart TVbr- Gravel patio, wood-burning fire pit, gas grillbr- 2 kayaksbr- Private dock, canal accessbrbrINDOOR LIVINGbr- 3 Smart TVsbr- Dining table, dry barbrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Dishware/flatware, children’s dinnerware, cooking basicsbr- Keurig coffee maker (starter pods provided)br- Blender, ice makerbr- Microwave, toaster, toaster ovenbrbrGENERALbr- Free WiFibr- Central A/C, ceiling fansbr- Central/electric heatingbr- Linens/towels, iron/boardbr- Washer/dryer (detergent provided)br- Trash bags, paper towelsbr- Hair dryer, complimentary toiletriesbrbrFAQbr- Pet fee (paid pre-trip)br- 4 exterior security cameras (facing out)brbrACCESSIBILITYbr- Single-story home, exterior stairs requiredbrbrPARKINGbr- Carport (2 vehicles)br- Gravel driveway (2 vehicles)brbr-- THE LOCATION --brbr- Walk to grocery store, coffee shop & restaurantbr- Near kayaking areas, boat rentals & fishing chartersbr- 11 miles to Sugarloaf Beach & 14 miles to Bahia Honda State Parkbr- 19 miles to Key West Tropical Forest & Botanical Gardenbr- 22 miles to Key West: Smathers Beach, parks, shops, galleries, cafes, bars, restaurantsbr- 21 miles to Key West International Airport & 138 miles to Miami International Airportbrbr-- 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 or vaping of any kind, including marijuanabr- Pet friendly w/ $90 fee (+ fees & taxes; dogs only, 1 max)br- No events, parties, or large gatheringsbr- Per Florida guidelines, guests must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This property sleeps 4 guests in 2 beds, with room for 6 total by using the queen air mattressbr- This single-story home requires exterior stairs to enterbr- Your safety matters. This property features 4 exterior security cameras: 1 camera is on the side facing the homeowner’s boat, 1 camera is in the carport facing the front yard and street, 1 camera is at the top of the entry stairs facing the staircase and side yard, and 1 camera is on the back facing the backyard and dock area. These cameras are outward facing and do not look into any interior spaces. They record sound and video when activated by motion
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$792.71

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Private Vacation Home

Latitudes - Ocean front with salt water pool.

Cudjoe Key, Florida, United States

This tropical 6 bedroom 4 bath oceanfront home has a private heated salt water pool and huge outdoor living space. There is beach access, shared dock space and outdoor gazebo to watch sunsets. There is a 3rd story balcony that offers spectacular views of the sunrise and sunset. Bring up to a 24' boat or paddle out on one of the shared kayaks onsite. Fully equipped kitchen, linens, beach towels, a propane BBQ grill and 2 washer/dryers.brThis home is priced based on the number of guests. brbrYour property manager lives nearby and is available if you have any requests during your staybrbrOcean front private location!brbrYou will be provided check in instructions prior to your arrival.brbrbrbr• Master Bedroom: 1 King bedbr• King Bedroom: 1 King bed br• King Bedroom: 1 King bedbr• King Bedroom: 1 King bed br• Queen Bedroom: 1 Queen bed br• Queen Bedroom: 1 Queen sleeper Sofabr• Living Room: Queen sleeper sofa, Flat screen TV, br• Kitchen: Fully stocked with blender, toaster, coffee maker, microwave oven. Full supply of; dishes, bowls, silverware, stemware, drinking glasses, pots, pans and utensils. br• Linens: All sheets, towels and beach towels provided. Iron and ironing board. br• Supplies: Dish soap, dishwasher soap, dish sponge, some large trash bags, bar soap and liquid hand soap in bathrooms, propane for grill, one full roll of paper towels, one extra full roll of toilet paper per bath. br• Outdoor Features: Propane BBQ,br• Boat Dockage: Tall pier for boats up to 24. The dock is shared with the Latitudes Home guests. The water is shallow, about a 2' draft getting out to the channel.br• Parking: Contract is for 2 cars and 1 boat trailer. Please let us know if you need additional parking. br• Central A/C: Not to be set below 70 degrees. br• Other: Washer/Dryer, ice maker in refrigerator, wireless internet, Smart TVsbr• Games: Corn Hole Gamebr• The dock, gazebo, kayaks and kayak launch area are shared with Latitudes Home guests. There are a couple kayaks for your use. You may rent additional kayaks locally.br• Location: 20 minutes from Key West, 15 minutes from Bahia Honda State Park. br• Pool: heated salt water pool. This is a private pool - not sharedbrbrbrCudjoe Key is the perfect get away spot...removed from the hassle but close enough to enjoy Key West or Bahia Honda State Park in about 20 minutes!brbrUber, Lyft and Taxis area available as well as Public Bus transportation. It is recommended that you have a carbrbrThis is a pet friendly home. A pet fee and approval of your pet is required.brPrior to your stay we require you to complete a pre-arrival form and sign and agree to our rental conditions.brbrThis home is priced based on the number of guests. The base rate is for up to 6 guests. Additional guests fee is $25 per night per person.brbrbrOur Cancellation policy is:brCancellation: If you cancel your reservation in writing 90 days or more before your arrival, you will receive a full refund, less a cancellation fee of $25.00 and Administrative fee. If you cancel less than 90 days before arrival, your payment and any prepaid rent will be refunded only if we are able to procure another rental for that same period. If no rental is procured, you will lose your payment and any prepaid rent, not to exceed the amount of your rental. If you cancel within 30 days of your arrival, there will be no refund. If The Florida Keys are closed to visitors because of the COVID-19 pandemic for your arrival date, you will be offered the opportunity to reschedule your reservation or receive a refund. brbrNon-Refundable Damage Deposit Waiver: Instead of charging a security deposit, Host charges a non-refundable $74 damage waiver fee that covers up to $3000 for damage to real or personal property of the vacation rental property as a result of your acts or omissions.
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$318.38

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Private Vacation Home

Ocean View High-Rise in Venture Out | Pool, Boat Ramp & close to Key West

Cudjoe Key, Florida, United States

Welcome to Casa Kiwi #472, your perfect getaway in the heart of the beautiful Florida Keys.brNestled on a serene interior large corner lot, this high-rise home offers stunning privacy surrounded by lush, vibrant vegetation and ocean views. Casa Kiwi is designed for relaxation and fun, making it the ideal spot for your next vacation. Step inside and you'll find an open floor plan that seamlessly connects the kitchen, dining room, and living room, creating a spacious and inviting atmosphere. The modern kitchen is fully equipped, ready for you to whip up delicious meals. The living space is comfortably furnished, providing the perfect setting for cozy evenings or lively gatherings.brThere is a 3 night minimum stay required at this home.brDISCOUNTS AVAILABLE - 10% off the nightly rate for stays of 7 nights or more. 22% off the nightly rate for stays of 30 days or more.brCasa Kiwi boasts two well-appointed bedrooms and two pristine bathrooms, ensuring a comfortable stay for all guests.brThe Primary Bedroom has a King size bed and an ensuite bathroom for privacy and convenience. brThe Guest Bedroom has a comfortable Queen size bed. This charming home comfortably accommodates up to 6 (4 Adults & 2 Children) guests. The covered porch, with its ample seating, is a true highlight. Overlooking the ocean, it's the perfect spot to enjoy your morning coffee, watch the sunrise, or simply relax with a good book while taking in the breathtaking views.brFor those who love outdoor activities, Casa Kiwi offers 4 bikes, perfect for exploring the scenic surroundings. The property also features a gas grill to cook up your fresh catch and a dedicated area for family gatherings, making it easy to enjoy al fresco dining and create lasting memories with loved ones.brStaying connected is a breeze with high-speed Wi-Fi provided here. There is a washer and dryer for your convenience meaning you can pack light and keep your wardrobe fresh throughout your stay.brThere is a Mr. Coffee drip and KCup Single Coffee Maker at this home for you to enjoy your favorite brew.brWhether you're seeking a peaceful retreat or a base for adventure, Casa Kiwi is the perfect choice for your Florida Keys rental. Come and experience the charm and beauty of this exceptional property, and make memories that will last a lifetime.brVenture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts.brAdventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away!brWhether you're a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key.brSorry, no pets allowed at this home.brLocated inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 25'L x 10'W. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay.brMain guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee. brSocial Media -br@bluescaperealestatebrYouTube Videos @bluescapevacations
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Exceptional(3)

$340.88

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Private Vacation Home

The Diving Dolphin #268 - Ocean Views, Kayaks!

Cudjoe Key, Florida, United States

The Diving Dolphin #268 - Waterfront Getaway | 2BR/2BA | Ocean Views, 2 Kayaks, 2 Bicycles, 2 Paddleboards, 35' Seawall & Pet-Friendly!brWelcome to your perfect island escape! This charming and clean two-bedroom, two-bath home sits right on a boating canal with beautiful ocean views and breathtaking sunrise scenes. Ideal for up to six guests, it's the perfect spot for relaxing, adventuring, and making memories.brInside, you'll find two cozy bedrooms, each with a queen-sized bed, TVs and two full bathrooms for your comfort. The Primary bedroom has an ensuite full bathroom and direct access to the back patio. The guest bedroom also has a sliding door for direct access to the back patio.brThere is a Queen size pull out sleeper sofa in the living room for additional sleeping accommodations.brThe fully equipped kitchen makes meal prep easy, featuring a dining table for four and a kitchen island with two barstools. There is a dishwasher for convenience and a Keurig coffee machine ready to brew up your favorite cup of coffee.brA dedicated laundry area with washer and dryer adds to the ease of your stay, and beach towels are provided for your sun-soaked adventures. brAdventure awaits right outside your door! Guests have access to two paddleboards, one kayak, one tandem kayak and two bicycles — perfect for exploring the surrounding islands and waterways. This location is a boater's dream with a 35' seawall, offering quick access to both the backcountry and offshore waters. There is a fish cleaning station and swim ladder on the dock for your convenience. A BBQ grill awaits to cook up your fresh catch of the day. Plenty of outdoor seating including a table and sun loungers to relax and enjoy the sea breezes! brWe're pet-friendly too! Bring along up to 1 small, under 40# dog maximum (with a $250 pet fee) so the whole family can enjoy the trip.brBook your stay today and experience the beauty, adventure, and relaxation that island life has to offer!brVenture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts.brAdventure beyond the gates for a bite to eat at some of Florida Keys favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away!brWhether you're a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the waters edge, our Florida Keys getaway promises an unforgettable vacation experience. Book your stay now and discover the ultimate blend of luxury, convenience, and coastal charm at our oceanfront retreat in Venture Out on Cudjoe Key.brLocated inside Venture Out on Cudjoe Key. A separate Registration Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. This fee must be paid with cash or credit card (4% credit card fee will apply). Parking for 1 vehicle per Unit. This vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 19'L x 10'W. If your vehicle does not fit when you arrive, you will need to see the guard gate for an additional parking pass for the overflow lot which costs $5/day. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay.brMain guest must be 25 years of age or older and will need to email a copy of your drivers license to the Rental Manager after booking has been accepted. The vacation rental agreement must be signed and returned within 24 hours of booking acceptance. There is a 4% credit card processing fee.brBook your stay today and experience the beauty of waterfront living!
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