Home Vacation Rentals By Owner In Cudjoe Key, FL

Showing 240 Of 287 Vacation Rentals
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Exceptional(142)

$245.18

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Private Vacation Home

Enjoy Caribbean weather in the USA. Openings June 2026 forward!

Cudjoe Key, Florida, United States

We have a big bright eat in fully stocked kitchen. Kitchen has many pots and pans, keurig, blender, glassware and most things that you’ll be looking for while relaxing in the beautiful Keys!! The main bedroom has a KING size bed, lots of storage space and TV with YouTube Live TV & Roku. brbrThe second bedroom has a twin trundle, when the two twin beds are side by side it's like another King Size Bed and TV with Roku & streaming YouTube Live TV. brbrWe're provided lots of fluffy cotton towels in the bathroom. We have a grill in our backyard along with cement patio furniture for you to enjoy the beautiful keys weather. The front porch has a large deck, seating for 6. You can enjoy the sunrise and your morning coffee, family dinners and evening cocktails!brbrBring your boat! We are on a dry lot but there is no charge for launching in at the Venture Out Marina, your boat can be stored in the 'overflow' lot for a small fee ($5-10 day subject to first come first serve availability). Conveniently located near the marina, picnic area, pool, tennis and rec hall. The Florida Keys have some of the best fishing in the world! (Boat and trailer parking is an additional daily charge by the park.) It is also a great spot for Kayaks. Take your choice to relax in the heated Olympic size salt water pool, hot tub or open Atlantic swimming area all nearby. You can fish from our open water areas. There is a big TIKI HUT on the open water where picnicking is perfect!brbrUnfortunately due to some bad experiences pets are no longer allowed. brbrOUR HOME IS NO SMOKING. Smoking outside is obviously permitted.brbrThe GATED COMMUNITY we own in is AWESOME & a very friendly place to stay & enjoy. The amenities include: 24 hour security, Lighted tennis courts (2 rackets available at the house) Olympic-sized heated pool, kiddie pool, spa Jacuzzi, ping pong, bocce ball courts (set of bocce balls in the closet), pickle ball, lighted basketball court, children's playground, pool table, darts, Marina complete with 2 ramps, gas, store, ATM and fish cleaning station, boat trailer parking onsite, open water picnic areas, ocean front tiki hut, lending library, post office - and MORE - ALL IN A GATED COMMUNITY with a mixture of RV sites and manufactured homes where you can feel safe and secure.brbrWe're only 19 miles from Key West, but do not think you HAVE to go anywhere - lay by the HUGE POOL right on the OPEN WATER and watch the elegant seagulls float overhead as the palms sway. Sun yourself and read a good book and simply relax! Plunge into the BIG JACUZZI and soak your troubles away. Or spend some time with someone you love - holding hands and watching the herons fishing along the waterside! And you do not even have to get in your car to do any of these!brbrAdventure 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! What are You waiting for Send an email and we'll fill you in on any of your questions to make certain your family and friends are going to have a great vacation getaway in the Keys! brbrMake sure you check our availability calendar as it is updated after each reservation is placed. Plan it now, before someone else gets YOUR Place!brbrOur home has parking for one vehicle but extra may be able to be stored in the nearby overflow lot for an additional fee of $5-10/night subject to availability. FYI a full size pick up will not fit in the driveway (we fit a Titan) and will need to go in the overflow lot with a nightly charge. There is an additional one time fee of $125 payable to the community at the time of entrance which is separate from anything paid to me through Vrbo. Would be willing to book direct if asked for discounted rate. Contact me at five zero eight 826-six two seven one. My phone number is also on rental agreement. brbrArrival time is 3:00 PM, Departure is 10:00 AMbrbrKeywords: House, home, bungalow, cottage
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Exceptional(51)

$238.14

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Private Vacation Home

Looking for a place to stay

Cudjoe Key, Florida, United States

Relax in our traditional keys style stilt home. The home is located on a channel with immediate access to the Atlantic Ocean. The concrete dock allows for easy access and quick drive to the open water. With the ocean at your whim, finding your favorite spots for fishing, lobstering, diving, and snorkeling has never been easier. Easy access to Content Islands.brbrThe home is conveniently located on Cudjoe Key, MM23, allowing for a 25 minute drive to famous Duval Street in Key West, or Marathon Key to the North. Our home is located far enough to relax and enjoy the serenity of the island life while close enough to take a night on the town.brbrThis three bedroom, two bath home features, one king bed, one queen bed, and two twin beds. The home has a beautiful back porch over looking the water where you can enjoy a good book, a glass of wine, or dinner with your loved ones. A spacious, fully equipped kitchen provides the perfect setting to create your favorite dishes or show off your grilling skills by cooking up some of the keys freshest seafood. brbrOur home is equipped with towels, ceiling fans, DVD player, radio, games, washer/dryer, iron/ ironing board, hair dryer, patio furniture, hammock and a gas BBQ grill. Now a pool.brbrRestaurants: brCudjoe Key has some of the best seafood restaurants in the Florida Keys including the Square Grouper, Mangrove Mamas, Boondocks (Live Music). These restaurants are within 2 to 4 miles from the home.brbrSports: brFor the active vacationers there are many activities: Snorkeling, scuba diving, fishing, water skiing. You can rent a boat or kayak, even swim with the dolphins. Bikes for rental at Big Pine Bicycle, delivery and pick up services to your location. There is also jets ski and kayaks renting nearby. They also deliver and pick up.brbrBooking starts in the beginning on the month and ends by the 30th. Flexibility is possible during slow season.brbrPets larger than 40 pounds are not accepted. Contact owner for any questions 5617140139.
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Exceptional(218)

$358.43

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Cottage

**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

Cudjoe Key, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrTIDEWATER VIEWS is a cozy 820 square foot cottage that has everything you want for the perfect tropical vacation: open water views from a covered porch, a private 35-foot boat slip, kayaks, bikes and access to the wonderful amenities at Venture Out, a residential community with a heated 80-foot pool with large Jacuzzi and Kiddie Pool, tennis courts, basketball court, bocce courts, swimming lagoon, marina and convenience market with fuel on site and two double wide boat ramps, Recreation Center with billiards, darts, and ping pong, post office and a library. Venture Out has 24 Hour Patrolled Security.brbrTHE COTTAGE...brbrTIDEWATER VIEWS has been recently remodeled to a high standard, with Smart TV’s in every room. You’ll enjoy all of the amenities you would expect back home: Dishwasher, Washer/Dryer, Microwave, Range, Refrigerator, Blender and other small appliances. This home accommodates up to 6 people in 2 bedrooms with queen beds and a queen sized sleep sofa with Tempurpedic mattress. You’ll be able to bring your boat to dock on the 35' concrete seawall equipped with dock posts, cleats, fish cleaning table & swim ladder. brbrTHE AREA...brbrThere are some wonderful places to explore, from Bahia Honda Beach (voted one of the top 10 beaches in the U.S.) and the American Shoal Lighthouse to snorkeling off Looe Key. For dinner out, consider the Square Grouper, Mangrove Mama’s and Tonio’s Seafood Shack just up the road. Last but not least, TIDEWATER VIEWS is just a 25-minute drive to either Key West or Marathon, with all their attractions.brbrALL LAST KEY VACATION HOMES INCLUDE: brbr** Washer and Dryer br** Central Heat and A/C br** Ceiling Fans Throughoutbr** Flat Screen Cable TVs in Living Room & Bedrooms br** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels provided br** Wireless high-speed Internet access and full cable is included br** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list: brbr** Patio Chairsbr** Fish Cleaning Stationbr** Seawall / Boat Dockagebr** Propane BBQ Grillbr** Queen Sleeper Sofa br** Community Pool Accessbr** Community Jacuzzi Spabr** Marina Store with Fuel onsitebr** Bait and Convenience Marketbr** Boat Wash Stationbr** Salt Water Swimming Lagoonbr** Post Officebr** Lighted Tennis, Basketball, and Bocce Courtsbr** Ping Pongbr** 4 Bikesbr** Off-Street Parking for 1 vehicle. Vehicles must be under ten feet (10’) in width and must not exceed forty feet (40’) total length.brbrOther notes: brbr** Interim housekeeping provided upon request br** This property will accommodate up to 6 adultsbr** Pets Allowed (dogs are not allowed to be walked in the neighborhood) - Max of 2 pets allowed and an additional fee of $200 per pet will applybr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.brbrIMPORTANT NOTE: Venture Out charges a one-time Registration/Resort Fee due upon arrival: $116.28 + $8.72 Tax = $125 for up to 6 people (Credit card or cash) PAID DIRECTLY TO VENTURE OUT. If you arrive with more than 6 people which is the maximum allowed in the home, you will not be permitted in the park. Venture Out guests are required to submit additional paperwork in advance of arrival, which Last Key will collect and coordinate within the week of your arrival. Guests should be prepared to submit all guest information to comply with HOA requirements.
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Exceptional(99)

$285.94

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Cottage

Fishermen’s Paradise

Cudjoe Key, Florida, United States

This is a water lover or a Fisherman’s Paradise. brThis waterfront home can sleep 6. The house is fully furnished with a colorful island vibe Modern 2 bedroom & 1 bathroombr.There is a queen bed in the master bedroom along with AC & a flat screen TV. Along side that is a connected/shared bathroom.brA full bed in second bedroom with AC & flat screen Tv. brThere is also A full pull out couch in the Florida room(living room area) with 2 AC units and a flat screen TV. br4 ACs units total I house.brbrbrThe decoration in all the rooms make it known your home but the feel of paradise.br The Florida room has a 4 person dining area. brThe kitchen has a Microwave,Stove/Oven, Keurig/ Coffee Maker,Fridge,Toaster. Unfortunately there is NO dishwasher or washer and dryer.brbrWe have Two bikes. There is a picnic table out front to enjoy your morning coffee. brThe back yard is waterfront with easy access to cut your fish and wash your boat off, outside lighting,power washer,Along with a gas grill to enjoying spending extra time outside while making your catch of the day. There is a 35 ft sea wall you are able to keep your boat at,it is one of the biggest in the neighborhood. This unit is also located a 3 minute walk to the nearest bath house to use your Coin laundry area and if needed for extra bathrooms and showers.brbrThe house is in a secured gated community called Venture Out,which is a 64 acre property with 24 hour security.brbrbr ***Please note, a additional one time charge (not included in your total and is not charged by the owner) of $125 is paid at gate time of arrival.***br brThat charge is to use all the amenities that Venture out has to offer which are all walking distance from the house. It includes Two boat ramps,fueling station,a convenient store(open 7 days a week)- the store alone has all last minute things you need from beer,food,snacks, toiletries,bait & ice, 80 ft heated pool(with ocean views) a children’s swimming area,hot tub,tied off saltwater swimming(next to the pool) with tiki huts to picnic under,washer & dryer units, and extra bathhouses & bathrooms. brbrIf your into certain sports or activities V.O has you covered also with a tennis court, basket ball court and pickle ball court. Along with the recreation building that has a library, pool tables,dart boards & ping pong and also WiFi! brbr***WiFi is ONLY located at recreation station and poolside***brbr** Will do 2 or 3 payment options for you upon request,just send me a message and let me know** brbrOnce booked I have a property manager that lives on site that can help with any questions or needs you may have. I will also be available for any questions during your whole stay! brbrPARKING- Each unit is only a one car driveway.brAdditional vehicles may be parked in the over flow parking lot (5 minutes away from your home) for $5 a night. Parking for Boats and/or trailers Must be parked outside of park -Accommodations of places will be giving after reservation. brbrDepending on the time of year the Pavilion has all different activities also from pancake breakfast,church,movies,Musicals,Swimming yoga,line dancing etc! brbrCudjoe Key is 20 miles from Key west. It is between Sugarloaf Key and Summerland Key and not far from Big Pine Key or Marathon. All year long there are different events, holidays,festivals,fishing tournaments, lobster season,boat races,fantasy fest etc.brbrBook with us today to enjoy the Beautiful Florida Keys!!
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Exceptional(6)

$329.65

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Private Vacation Home

Sailfish Haven #390 - Ocean Views, 35' seawall

Cudjoe Key, Florida, United States

Florida Keys Waterfront Retreat with Stunning Ocean ViewsbrWelcome to your perfect getaway at Sailfish Haven #390! This beautiful 2-bedroom, 2-bath home offers everything you need for a relaxing and enjoyable Florida Keys vacation. Situated on a quiet canal, you'll be captivated by breathtaking ocean views from your private back patio, where you can unwind and soak in the scenery.brKey Features:br*Spacious Bedrooms: Two cozy bedrooms designed for comfort, ensuring restful nights after your adventures.brThere is a Queen size bed in the primary bedroom and a Queen size bed in the guest bedroom.brThere is also a Queen size air mattress located in the Guest bedroom closet for additional sleeping options.br*Two full Bathrooms, one is located in the primary bedroom, both have standup showers.br*Roku TVs are located in the Living Room and Primary Bedroom.br*Outdoor Oasis: Enjoy the expansive 35' concrete seawall that can accommodate up to a 32' boat—ideal for fishing, swimming (a new swim ladder just installed!), sunbathing, or simply enjoying the gentle ocean breeze. Under the house is a fisherman's paradise equipped deep freeze/bait freezer, room for your fishing gear and mini fridge for your beverage of choice.br*Fish Cleaning Station: For the anglers among you, our dedicated fish cleaning station makes it easy to prepare your catch of the day.br*Outdoor BBQ Char Broil Patio Bistro - an electric grill perfect to cook up your fresh catch! br*Open Kitchen & Dining: The fully equipped kitchen opens to a welcoming dining area that comfortably seats up to 4, perfect for family meals or entertaining friends. Equipped with slow cooker, wine chiller and extra bar top seating for 4. There is a Mr. Coffee coffee maker and a single cup Keurig at this home for you to enjoy your favorite brew. br*In the dining area you will enjoy dining with a view with 4 seats at the dining table.br*Laundry Facilities: A washer and dryer are available within the home, so you can pack light and keep your clothes fresh throughout your stay.br*Two bicycles are provided for guest use, along with one single and one tandem kayak. A signed waiver is required prior to use.brWhether you're here for a weekend getaway or an extended vacation, our waterfront retreat promises a unique blend of relaxation and adventure. Explore the local attractions, enjoy the water activities, or simply kick back and enjoy the stunning views from your patio.brThis is a pet friendly home! Up to 2 dogs allowed with an additional pet fee of $250 per pet. If you are bringing dogs, please inform us at time of booking.brbrVenture 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 all of the onsite 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 12.5'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 or you may pay with an e-check with no additional charges. **PLEASE NOTE IF YOU ARE PAYING WITH AN E-CHECK, THIS PAYMENT OPTION IS THE SAME AS PAYING WITH A PAPER CHECK. IF YOUR E-CHECK IS RETURNED FOR ANY REASON, YOU WILL BE CHARGED A $25 RETURNED CHECK FEE AND BE REQUIRED TO PAY VIA CREDIT CARD WITH 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(18)

$325.94

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Condo

Sirena Key Cottage in Venture Out

Cudjoe Key, Florida, United States

VO365brSirena Key Cottagebr​​​​​​​ 35' SeawallbrIt's a wonderful time to enjoy Paradise! Quick ocean side access to gulf and ocean, near Looe Key Reef. Main living room overlooking water with two sliders off open porch to bring the outdoors in. Master suite with queen size bed with full bathroom and lots of closet storage and stack washer/dryer. Guest bedroom full bed and bathroom with stand up shower. Amenities include central air conditioning, ceiling fans, tile floor, outdoor patio furniture. Unit includes 2 bikes, kayaks and a Golf Cart available for a fee per day. Waiver must be signed at office. brbrWe are located in a spotlessly clean gated community with 24 hr. security, marina, ship store, boat ramps, picnic garden, heated pool, hot tub, tennis, basketball, playground, pickle ball, bocce ball and tennis, pavilion and club house for activities, over 4 miles of paved streets. brIt's a wonderful community with full time residents and vacation renters alike! brSECURITY DEPOSIT REQUIRED, NO SMOKING, br7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL,brOVERFLOW PARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brVO REGISTRATION FEE $125.00- DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.br****VEHICLE MAY NOT HANG INTO STREET- GUEST MUST VERIFY PRIOR TO RESERVING****
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Exceptional(9)

$313.85

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Private Vacation Home

Reel Island Retreat #273 at Venture Out in the Florida Keys

Cudjoe Key, Florida, United States

Take that vacation you have been dreaming of in the Florida Keys! Reel Island Retreat #273 is waiting for you!brPerfect for Boaters and Families - Welcome to your dream vacation rental on this serene boating canal with stunning ocean views from the patio.brThis charming 2 Bedroom, 1.5 Bath home offers breathtaking open water views from the back porch, making it an ideal escape for avid boaters, fishermen, or families and couples looking to unwind.brHighlights of Your Stay:br*Spacious Accommodations: - The front bedroom features a king sized bed with the popular green tea cooling mattress!br- The back bedroom boasts a cozy full-size bed and includes a convenient half bath for your privacy and ease.br*Living Space: - Relax in the inviting living room equipped with a pull-out sofa bed, perfect for accommodating extra guests. Enjoy your favorite shows on the ROKU TV, available in the living room and both bedrooms.br*Outdoor Bliss: - Step outside to your private dock with 35' of concrete seawall that can accommodate up to a 32' boat, where you can grill up a delicious BBQ feast while enjoying the tranquil ocean views. You may even spot a manatee swimming by in the canals!br*Tiki Bar Vibes: - Unwind at your very own indoor “Tiki Bar,” the perfect spot to sip cocktails and share stories after a sun-soaked day on the water.br*Location: Nestled in a prime location for boating adventures, you'll have easy access to fishing spots and scenic waterways. Whether you're casting a line or soaking up the sun, this home is designed for relaxation and enjoyment. There is a Keurig & Mr. Coffee Drip coffee maker at this home for you to enjoy your favorite brew. brBook your stay today and create unforgettable memories in this picturesque canal retreat!brThis is a pet friendly home. Up to 2 dogs maximum are allowed with a paid $250 pet fee per pet. Rental Manager must be notified at time of booking. 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, Kikis 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 20'L x 11'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 @bluescapevacationsbrBook your stay today and experience the beauty of waterfront living!
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Exceptional(88)

$828.85

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Private Vacation Home

Fandango - private pool
This is a pet friendly home. A pet fee and approval of your pet is required.

Cudjoe Key, Florida, United States

This house includes all the elements you need for an amazing vacation. Outside the house there are kayaks for adventures, a swimming pool, Hot tub, private beach area with loungers and Beach chairs for relaxation, a floating dock for fishing and docking a boat up to 24’, tropical foliage including coconut palms and bananas, a screened in porch for dining al fresco and so much more.brbrYour property manager lives nearby and is available if you have any requests during your staybrbrQuiet neighborhood – Quiet hours are 10 pm to 8 ambrbrYou will be provided with check in instructions prior to your arrival.brbrThis house includes all the elements you need for an amazing vacation. Outside the house there are kayaks for adventures, a swimming pool, Hot tub, private beach area with loungers and Beach chairs for relaxation, a floating dock for fishing and docking a boat up to 24’, tropical foliage including coconut palms and bananas, a screened in porch for dining al fresco and so much more. Inside the house there are 4 king bedrooms and a 5th bedroom with a queen bed and a single bed, 3 baths, open floor plan with plenty of living space, smart TV’s and updated appliances. Bed linens, bath and beach towels are provided. The kitchen is fully stocked for a home cooked meal with pots, pans, utensils, blender, toaster and Coffee Maker (auto drip and Keurig). This home has everything you need to provide you with an ultimate vacation experience. Welcome to your home away from home. brFandango is centrally located in the Lower Florida Keys at MM21.5. It is 20 minutes from Key West, 10 minutes from Big Pine Key and 15 minutes from Bahia Honda State Park. There is a 5 star restaurant within a mile and tiki bars and other restaurants within 10 miles. There is a bus stop within walking distance that goes into Key West. You do need a vehicle for grocery shopping and getting around. brbrbrCancellation: 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 for weather related or other emergencies for your arrival date, you will be given the opportunity to re-schedule 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.brbrUber, Lyft and Taxis area available as well as Public Bus transportation. It is recommended that you have a carbrbrPrior to your stay, we require you to complete a pre-arrival form and sign & agree to our rental conditions.brThis 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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Exceptional(10)

$313.88

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Private Vacation Home

Pelican's Roost, Waterfront comfort at Venture Out

Cudjoe Key, Florida, United States

About this spacebrPelicans Roost is a waterfront home on the Atlantic side of Cudjoe Key with a 17’ dock. Only 20 miles from historic Key West. Explore the lower keys from this great central location. Big Pine is only 8 miles away, Bahia Honda state park only 16 miles. Also plenty of family friendly activities within the Venture Out Resort like a hot tub, pool, tennis courts, pickle ball, basket ball, a private beach with tikis for beautiful ocean viewing and a community store. A perfect home for your adventurebrThe spacebrComfortable 2 bedroom 2 bathroom, the master bedroom has a comfortable king. The second bedroom has two twins that can convert to a king.brGuest accessbrSomething to note;brThere is a, non refundable, $125 fee to access the Venture Out community and is paid directly to Venture Out upon arrival. This is separate of your booking charges. The fee is collected at the entrance gate and is subject to a convenience fee if you choose to use a credit card. brGuests have access to the entire home along with all of the amenities inside of Venture Out. A key code will be sent along with instructions before arrival once the booking is complete and the rental agreement and $300 security hold have been processed. brJust a few reasons we LOVE the KeysbrbrJohn Pennecamp ParkbrJacobs Aquatic CenterbrHarry Harris ParkbrAfrican Queen Canal CruisebrFounders parkbrRobbiesbrHistory of Dive MuseumbrTheater of the SeabrThe Lagoon & Bongos at Grassy KeybrFlorida Keys Aquarium EncountersbrAir MuseumbrCrane PointebrSombrero BeachbrDolphins Research CenterbrTurtle HospitalbrMarathon Community ParkbrSunset Grillebr7 mile Bridge walkbrPigeon KeybrBahia HondabrVeterans ParkbrThe Horshoe swimming holebrFish the bridges with LandBoat ChartersbrVisit the Key Deer on Big Pine KeybrNo Name PubbrVisit the Blue Hole and Marillo trail on Key Deer Blvd.brBig Pine Key community park (skate and bike)brBig Pine Flea market brKiki'sbrBoondocks and Mini Golf and Saturday marketbrVisit Fat Albert at the end of Blimp RdbrSugarloaf Wednesday Farmer’s Market brSkydive Key WestbrEat lunch and Kayak the mangroves from Geiger Key MarinabrHurricane Hole (play area)brSheriff's Dept Animal FarmbrSmathers BeachbrEast Martello tourbrWest Martello/Key West Garden ClubbrHiggs Beach, Park, piersbrSalute on the BeachbrSNUBA of KW (5+)brRent bikes and EXPLORE!brRent kayaks and EXPLOREbrTrolley tourbrTrain tourbrLighthousebrHemmingway HousebrCurry Mansion (crows nest!)brKW AquariumbrShipwreck museumbrMel Fisher MuseumbrWaterfront brewery (video games)brSunset at Mallory SquarebrButterfly museum brVisit the MANY art galleriesbrTruman Waterfront park &brSplash padbrFt. Zach brPeak ChartersbrSunset cruisesbrSandbar trips…
Bed 2

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Sleep 5

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$152.38

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Caravan Park/Campsite

Private RV Lot w/ 20' Seawall (17' Boat Max) | Pool, Marina & Amenities

Cudjoe Key, Florida, United States

Welcome to your Florida Keys escape at RV Lot #239 inside the gated community of Venture Out on Cudjoe Key. This recreational lot offers a relaxed island setting with beautiful landscaping that adds privacy and a more tucked-away feel.brThe lot measures approximately 64' x 22' x 70' x 20' and features 20 feet of seawall, accommodating a boat up to 17'. It is equipped with water and sewer hookups along with both 30 and 50 amp service to comfortably support your RV.brThe current photos show an RV on the lot- updated photos coming May 1.brPlease note this is for an RV lot only. There is no RV on site.brNo cable or WiFi service is provided at this lot.brEnjoy mornings under the palms and evenings outdoors on your spacious lot, perfect for relaxing after a day on the water. Whether you are boating, fishing, or simply enjoying the laid-back Keys lifestyle, this property provides a comfortable home base inside one of the Lower Keys' most amenity-rich communities.brCommunity Amenities at Venture OutbrVenture Out is one of the most amenity-rich communities in the Lower Florida Keys, offering:brMarina store with fuel, bait, and convenience itemsbrBoat ramp and wash-down stationbrBeautiful stretch of island along the oceanfront with many thatched roof umbrellas and loungers to take in the clean ocean breezes and relaxbrMassive 80' heated saltwater swimming pool, hot tub, kiddie pool, and saltwater swimming lagoonbrTennis courts, basketball, bocce, and pickleballbrOn-site marina store/market and post officebrElectric Golf cart-friendly streets throughout the communitybrLocationbrYou're just minutes from popular local favorites including Square Grouper, Morning Joint, The Bent Prop, Broil, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House with mini golf, all within a 10-minute drive. Key West is only 20 minutes away, offering additional dining, nightlife, and iconic attractions. brGood to KnowbrThis is a pet friendly property- Up to 2 dogs allowed.brGolf cart rentals available: $50 per day, subject to availabilitybrVenture Out registration fee: $125 (subject to change), paid directly to the community at arrival (cash or credit card; processing fees apply)brParking: 1 vehicle per lot. Your RV and vehicle must fit on the lot.brCommunity rules: Guests must follow all Venture Out rules and regulations, including quiet hours from 10:00 PM to 6:00 AMbrAge requirement: Primary guest must be 25 years of age or olderbrPayment & Booking RequirementsbrSigned rental agreement and government-issued ID 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 paymentsbrWhether you're here for world-class Atlantic and Gulf backcountry fishing, boating adventures, or relaxed evenings by the water, RV Lot #239 offers a comfortable, well-equipped spot for your Florida Keys vacation.
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$264.42

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Private Vacation Home

Gasparilla Villa - Your Ocean View Oasis on Cudjoe Key - Sunset Views!

Cudjoe Key, Florida, United States

Gasparilla Villa - Your Ocean View Oasis on Cudjoe Key - Sunset Views!brEscape to paradise in this luxurious 3 bedroom, 2 bath ocean view, canal-front home located in the Lower Florida Keys on Cudjoe Key. Perfect for families, this spacious retreat offers everything you need for an unforgettable vacation experience. Step inside to discover a fully stocked and updated kitchen, where you can prepare delicious meals using fresh local ingredients such as your very own catch of the day! There is a Keurig coffee maker at this home for you to enjoy your favorite brew.brThe open-concept living and dining area provide ample space for relaxing and entertaining, while large windows offer stunning views of the ocean and surrounding tropical landscape. Outside, the expansive outdoor balcony is the perfect spot for enjoying cocktails with friends or dining al fresco.brThe Primary Bedroom is on the main level of the home and features a King size bed and attached balcony to take in the views. There is also a bathroom attached to Primary Bedroom for privacy and comfort.brUpstairs, there are 2 Guest bedrooms and 1 bath. One of the guest bedrooms features a Queen size bed and a private balcony to sit and enjoy the ocean views. The 2nd Guest bedrooms features 1 Queen size bed and a Double size bed.brDownstairs you will find a 36' dock to store your boat and can accommodate up to a 36' boat. There is also fish cleaning station and bait freezer. As a bonus a private outdoor shower is located on the back of the house to rinse off after a full day on the ocean. Plenty of seating areas downstairs and sun loungers for you to enjoy. In the downstairs room, there is an air hockey table to challenge your friends to a game. There are 2 bicycles and 3 kayaks for you to explore around on. The yard is fully fenced for privacy!brPlus, you'll be just a stone's throw away from a variety of local favorite restaurants, including the Square Grouper Bar and Grill, Morning Joint Coffee, the Bent Prop, Boondocks Miniature Golf & Draft House, and Tonio's Seafood Shack & Tiki Bar. Whether you're seeking adventure on the water or simply craving relaxation in a tropical oasis, this canal-front home offers the perfect escape for your next getaway. Book your stay today and experience the ultimate Florida Keys vacation!brThis home accommodates up to 2 cars and 1 trailer. If you require additional parking, please contact us to check if extra vehicles can be accommodated. brThis is a 28-night minimum rental per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 years of age or older. Overnight occupancy is limited to a maximum of 6 people, and all guests need to be registered with the Rental manager. No smoking. This home is pet friendly up to 1 dog that is 30# maximum and payment of a non-refundable pet fee of $250. Utilities are included within reason. All reservations subject to final approval from the local Rental Manager. Online bookings accepted with approval from the Rental Manager within 24 hours. There is a 4% credit card processing fee. The vacation rental contract must be signed and returned after speaking with the Rental Manager for the reservation to be confirmed.
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Exceptional(29)

$214.13

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Private Vacation Home

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key, Florida, United States

We are offering a nice discount in May of 2023 because we are putting in a new dock.brbrWonderful, pet-friendly, and beautifully decorated 3/2 home on the water that’s perfect for a vacation or simply relaxation. It’s located on beautiful Cudjoe Gardens Key with direct ocean access with no bridges. There’s a marina within walking or rowing distance. Check out the nearby Marvin Key video.brbrSummary:brInternet - IncludedbrKayaks - IncludedbrCanoe - IncludedbrPaddleboards (SUPs) - includedbrLife vest and paddles - IncludedbrFlat-screen TV's in every room and movies - U-Verse, Netflix and Disney+brPets - AllowedbrWater Access - No bridges to Atlantic, easy access to GulfbrDockage - 80 feet availablebrFloating Dock - available for kayaksbrControl depth - 3 to 4 feetbrMarina and boat ramp - just blocks awaybrAppliances - full kitchen and laundry roombrBait and fish freezer - includedbrEasy access digital door - IncludedbrBBQ equipmentbrBeach chairsbr--- Weber Grill - IncludedbrTools of the Trade Non-Stick Cookware and knife Set (Macy's Brand).brbrWhy rent paddle equipment when our vacation rental includes multiple standup paddle-boards (SUPs), kayaks, Canoes, life vests, and paddles. We are constantly updating our paddling gear so check back often. We recently moved a canoe from the other location to this row fleet.brbrThe living room is spacious, and we have installed smart devices in the primary living area to make your stay more enjoyable. You can use Google assistant to check on the weather and even control how bright or dim the lights should be. We offer free high-speed internet and smart TVs in every room.brbrThe kitchen has lovely appliances, and we recently installed a new microwave and air fryer for those looking for healthier alternatives. There's even a freezer outside that can be used for bait and your fresh catch. We offer both a traditional coffee machine and a Keurig K-Compact for those seeking something different ( feel free to bring your favorite flavors).brbrOceanside and Gulf side boating await for those interested in exploring the Keys. If you hire a guide, you can explore offshore beaches on the Gulf side that we consider comparable or better than many of the beaches on Dr. Beach's list. Every once in awhile a seaplane will take someone to these beaches because the locations are just so wonderful (see the video someone posted about Marvin Key which is in the backcountry).brbrWe are really working hard on our BBQ and grilling capabilities. We acquired a Weber grill.brbrLooe Key Reef is an easy trip by boat or charter. The home itself is has a great screened in area that overlooks the swimming canal. Great place to have a cup of coffee in the morning or night. Inside you’ll find a warm, comfortable home that’s completely furnished and ready to go. There is plenty of parking, so you do not have to pay to store your trailer somewhere else. brbrFor relaxation purposes, we have installed wall-mounted 4K Ultra high-definition TVs with Chromecast built-in. These TVs are smartly connected to the wifi provided by AT&T fiber. Netflix, AT&T, and Disney+ are available. Of course, all trademarks and content belong to Google, Disney, AT&T, ESPN, and Netflix.brbrSmart Home:brJust ask Google a question, Hey Google, what's the weather outlook. Or, Hey Google, play some inspirational music on 'inside'. You may also control the temperature, Hey Google, set the temperature to 76 degrees on all devices - there are three devices.brbrIt's also useful to have Google call local services for you. For example, Hey Google, call Cudjoe Gardens marina.brbrSince Google controls the living room lights you can always say things like, Hey Google dim the lights or Hey Google, turn the lights to blue.brbrKeywords: Waterfront, Dock (80 foot of dockage on a deep canal), Oceanside, no bridge, very near Key West. Kayaks).brbrThis home only rents with a minimum of 28 days. Sorry, there are no weekly rentals allowed.
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Bath 2

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Sleep 8

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