Vacation Home Rentals By Owner In Cudjoe Key, FL

Tarpon Alley - VO509brCanal Front35' DockagebrbrCasually elegant, beautifully decorated, and fully stocked for your convenience and enjoyment, this 35-foot canal-front 2-Bedroom 2-Bath home comfortably sleeps six. Interior includes all tile flooring, transom windows, two queen beds, double sleeper sofa, 3 flat-screen TVs, internet/cable, and full line of appliances including washer, dryer, coffee maker, air fryer, Insta pot, crock pot, and George Foreman grill. Dock amenities include posts, cleats and fish table with running water. Downstairs includes covered parking, full size gas grill, outdoor shower, bicycles, inside storage space, bait freezer, and outdoor seating with tables upstairs and downstairs. Conveniently located just minutes from the on-property marina, pool, convenience store and recreation center.brNo Pets / No SmokingbrbrSECURITY DEPOSIT REQUIRED, 7 DAY MINIMUM LOBSTER SEASON,brFREE WI-FI IN THE 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-brGUEST MUST VERIFY PRIOR TO RESERVING****

Tarpon Alley - Venture Out 509

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$311.57

Canal Front 2BR/2BA in Venture Out with Ocean Views, 35' Seawall, Golf Cart Option & Pet-Friendly Island LivingbrWelcome to Island Time #110, a beautifully positioned canal-front retreat located inside the private, gated community of Venture Out on Cudjoe Key in the Lower Florida Keys. Situated at the end of a peaceful canal with breathtaking blue water views, this 2-bedroom, 2-bath home offers the perfect blend of boating, relaxation, and laid-back island charm.brWake up to stunning sunrises, enjoy your coffee while pelicans glide overhead, and settle into the true Florida Keys lifestyle.brThe SpacebrIsland Time #110 comfortably accommodates up to 6 guests and is thoughtfully designed for families, couples, anglers, and boating enthusiasts looking for a relaxing waterfront escape.brThe spacious living room offers comfortable seating and includes a queen-size pull-out sleeper sofa, providing additional sleeping accommodations when needed. Large windows bring in natural light and showcase the beautiful canal and ocean views that make this home so special.brThe fully equipped kitchen provides everything needed for preparing meals during your stay and includes both a Keurig single-cup coffee maker and a Mr. Coffee drip coffee maker so guests can enjoy their preferred morning brew.brCentral A/C, Wi-Fi, and an in-home washer and dryer are provided for added comfort and convenience throughout your stay.brBedrooms & Sleeping ArrangementsbrPrimary Bedroom: King-size bed and private ensuite bathroom with stand-up showerbrGuest Bedroom: Twin-over-queen bunk bedbrLiving Room: Queen-size sleeper sofabrMaximum Occupancy: 6 GuestsbrBathroomsbrPrimary Bathroom: Ensuite full bathroom with stand-up showerbrGuest Bathroom: Full bathroom with stand-up showerbrOutdoor Living & Waterfront ViewsbrIsland Time #110 is all about enjoying the outdoors and taking in the beautiful waterfront setting. The backyard offers stunning open blue water views at the end of the canal, creating the perfect spot for morning coffee, sunset cocktails, or simply relaxing and enjoying the ocean breeze.brBoaters and anglers will love the private 35' seawall, which can accommodate boats up to approximately 30 feet. The property also features a dedicated fish cleaning station, making it easy to prepare your catch after a day on the water.brAdditional outdoor amenities include:br2 bicycles for exploring Venture Out and nearby local spotsbrOptional golf cart rental available for an additional fee:br$40/day - $200/week - $550/monthbrGuests interested in reserving the golf cart should notify the rental manager prior to arrivalbrCommunity Amenities at Venture OutbrVenture Out is one of the most amenity-rich waterfront communities in the Lower Florida Keys and offers guests access to: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 oceanfront common areasbrGated security and electric golf cart-friendly streets throughout the communitybrLocationbrConveniently located on Cudjoe Key, Island Time #110 places you close to many of the Lower Keys' favorite restaurants, bars, and attractions including Square Grouper, Morning Joint, The Bent Prop, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House & Miniature Golf.brThe property is also located near world-class boating, fishing, snorkeling, diving, and the famous Looe Key Reef.brFor additional nightlife, shopping, dining, and entertainment, Key West is only about 25 minutes away.brPet-Friendly DetailsbrThis property is pet-friendly for up to 2 dogs with a paid pet fee of $250 per pet. Guests must notify the rental manager at the time of booking if bringing pets.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. Driveway measures approximately 19' long x 10' wide and vehicles must fit fully within the driveway without extending into the roadwaybrOverflow parking may be available through Venture Out for an additional 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 boating the backcountry, fishing the flats, enjoying sunset cruises, or simply relaxing beside the water, Island Time #110 delivers the perfect Florida Keys vacation experience with unbeatable waterfront views and true island-style living.

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$607.43

Our oceanfront oasis with a private heated saltwater pool, private dock for a boat up to 30`, kayaks and bikes! brbrOur 4 bed, 3 bath home has 2 king master suites, queen room, and a bunk room. brbrKitchen is stocked with essentials: laundry & dishwasher soap, paper towels, and toilet paper. Keurig or a traditional coffee pot. Free high-speed WiFi to keep you connected.brbrLounge poolside, fish off the dock, or explore nearby reefs. Tucked on a quiet street in Cudjoe Key, just 30 mins to Key West.br2 cars permitted. Private dock space for a 30` boat.

Gorgeous Newer Oceanfront Home! Private heated pool, dock and great views!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$647.98

Oceanfront Island Escape | 2BR/2BA Home in Venture Out with 35' Seawall & Sunrise ViewsbrWelcome to your tropical escape here at Casa Tartaruga #56 in Venture Out on Cudjoe Key — a brand new 2-bedroom, 2-bath oceanfront gem with uninterrupted turquoise water views and all the charm of island living.brPerched directly on the Atlantic Ocean with a 35' seawall perfect for boats up to 32', this vibrant coastal retreat offers the best of Keys life—whether you're boating, grilling, or simply swaying in a rocking chair at sunrise. Sip your morning coffee on the oceanfront balcony, where manatees drift past the canal and egrets and pelicans glide overhead, adding to the tranquil rhythm of the island.brInside, this home is a breezy blend of comfort and coastal elegance. The open-concept living area is flooded with natural light from oversized windows and sliding glass doors that frame the endless sea. The fully equipped kitchen features stainless steel appliances, a kitchen island, a Hamilton Duo - Drip and Single Cup Coffee Maker for you to enjoy your favorite brew, and fridge with ice maker & water dispenser—everything you need to whip up fresh-caught seafood feasts.brThe primary suite boasts a plush king bed, ensuite bathroom with tiled glass shower, and its own TV for cozy evenings. The guest bedroom features two twin beds that convert to a king, its own private balcony, and another full bathroom is just steps away with a stand-up shower. The living room has a queen pull-out sleeper sofa for additional sleeping accommodations.brOutside, unwind on the lower level with an outdoor dining table for six, a Weber grill, comfortable lounge seating, and a fish cleaning station ready for your daily catch.brWhether you're here to explore the reefs, fish from your backyard, or simply soak up the sun with a salty breeze in your hair, this home is the perfect base for your next Florida Keys getaway.brHighlights:br*Direct oceanfront with unobstructed water viewsbr*35' seawall with dock posts – bring your boat!br*Sunrise-facing open balcony with double rocking chairbr*Manatees & seabird sightingsbr*2BR/2BA (King + Twins that convert to King)br*Fully equipped kitchen with island & coastal décor throughoutbr*TVs in both bedrooms + ceiling fans in each roombr*Downstairs living space with grill, sofa, & dining table for 6brSoak in the sun. Savor the sea. Stay awhile in your own slice of oceanfront paradise.brWhether you are 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 a paid pet fee of $250 per pet. Rental Manager must be notified at time of booking.brThis home has a ring camera at the front door. A 4-seater electric golf cart is available for an additional fee: $50 per day, $250 per week, or $750 per month. Perfect for cruising around Venture Out and exploring the community with ease. Please contact the rental manager to add this to your reservation.brWelcome to Venture Out on Cudjoe Key – A Private, Gated Coastal CommunitybrExperience the charm of Venture Out, a golf cart-friendly, oceanfront neighborhood in the Lower Keys offering one of the most amenity-rich settings in the Florida Keys. Whether you're seeking adventure or relaxation, this private community has something for everyone:br*Full-Service onsite ship store with Fuel, Bait & Convenience Storebr*Boat Wash-Down Stationbr*Olympic-Style Heated 80' Pool + Jacuzzibr*Kiddie Pool & Saltwater Swimming Lagoonbr*Lighted Tennis Courts, Pickleball Courts, Bocce, & Basketball Courtsbr*Onsite Post Office & Market for Daily EssentialsbrHungry You're just minutes away from local favorites like Square Grouper, The Bent Prop, Morning Joint, Mangrove Mama's, Kiki's Sandbar, and Boondocks Draft House with Mini Golf — all within a 10-minute drive. If you're craving the buzz of Duval Street, Key West is just 20 minutes away.brWhether you're an avid boater, a fishing enthusiast, or simply ready to unwind by the water, your oceanfront stay in Venture Out promises the perfect blend of comfort, convenience, and coastal living.brNeed-to-Know Information Before You Book:brCommunity Registration Fee: A $125 fee (subject to change) is required by the Venture Out HOA. This must be paid at the guard gate upon arrival (cash or credit card; 4% credit card fee applies).brParking: 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 91/2'W x 12'H. 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.brOccupancy Limit: Strictly limited to 6 guests total, including infants and children.brMinimum Age Requirement: The primary guest must be 25 years or older and must email a copy of their valid driver's license to the rental manager within 24 hours of booking acceptance.brRental Agreement: Must be signed and returned within 24 hours of booking confirmation.brPayment Details: A 4% fee applies to credit card payments. brCommunity Rules: Guests are required to follow all Neighborhood Association rules and regulations. Violations may result in fines or immediate removal from the property without refund.brNo Smoking allowed in the home.

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Cudjoe Key, Florida, United States

Bed

Bath

4

Sleeps

$394.76

House A - You're in the tropics... listen to the waves, rest, relax or fish, kayak and snorkel, if you wish to lose a few pounds. Three bedroom, two bath home, with direct ocean access, boat parking at the back door. Sunrise view, ocean breezes. Fully furnished, linens, cable/internet. This home is on a compound, we also have several one bedroom units as well as 2 bedroom. The perfect spot for weddings, reunions, or large groups! Broil Restaurant is just across the street, Square Grouper restaurant and bar in the is down the street. Shuttle to Key West just steps from the home. Come and stay with us, you're sure to have a wonderful vacation.

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$485.99

Wastin' Away Again #468 is your perfect Florida Keys escape - a beautifully appointed 2 bedroom, 2 bathroom waterfront retreat with open water views, a 35' seawall, and everything you need for a relaxed island stay. Designed with comfort and functionality in mind, this home blends coastal charm with modern conveniences, making it ideal for boaters, anglers, remote workers, and families alike.brStep outside and enjoy true Keys living. The 35' seawall accommodates boats up to 32', and the private fish-cleaning station makes prepping your fresh catch easy after a day on the water. Fire up the Charbroil propane grill or gather around the outdoor dining area with seating for six to enjoy sunsets, ocean breezes, and laid-back evenings.brInside, the bright open-concept living space features central A/C, high-speed WiFi, and comfortable seating centered around a 50'' Smart TV - perfect for relaxing after a day exploring the Keys. The fully equipped kitchen includes stainless steel appliances, plenty of cookware, and a Hamilton Beach FlexBrew 14-cup coffee maker so you can enjoy your favorite brew each morning. The dining area offers a table with four chairs plus two additional seats at the kitchen bar.brBoth bedrooms feature king beds for a restful night's sleep. The primary suite includes a 32'' Smart TV and a private ensuite bathroom with a walk-in shower. The guest bedroom also offers a 32'' smart tv. The guest bathroom is located in the hall and features a convenient shower/tub combination.brNeed extra sleeping space The living room sofa pulls out to a full-size bed for additional guests. An in-unit washer and dryer adds convenience for longer stays, and the open water views create the perfect backdrop for your Florida Keys getaway.brWhether you're here for boating, fishing, or simply unwinding by the water, Wastin' Away Again #468 delivers the classic island lifestyle with the comforts of home.No pets are allowed at this home. There is one security camera underneath the house facing the canal. Venture 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, saltwater swimming lagoon, post office, and lighted tennis, basketball, and bocce courts. Adventure beyond the gates for a bite to eat at some of the Florida Keys' favorite restaurants such as Square Grouper, The Morning Joint, The Bent Prop, Mangrove Mama's, Kiki's Sandbar, or Boondocks Draft House and Miniature Golf—each just a short 10-minute drive away. Or head a little further south to Key West for even more island fun, only 20 minutes away. Whether you're a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the water's edge, this Florida Keys getaway promises an unforgettable vacation experience. Located 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 applies). Parking for 1 vehicle per unit. The vehicle must fit on the driveway and not extend out to the road. The driveway measurements are 18'Lx8;10''Wx7'2''H. If your vehicle does not fit when you arrive, please see the guard gate for an additional parking pass for the overflow lot, which costs $5 per day. Extra parking permits may be available for a maximum of 14 days depending on availability. Guests must follow all Venture Out rules and regulations during their stay. The main guest must be 25 years of age or older and will need to email a copy of their 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. Follow us on social media: YouTube: @bluescapevacations Book your stay today and experience the beauty of waterfront living in the Florida Keys!

Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$331.88

Please see our other property if you do not see your dates available! Property # 2092236brhttps://www.vrbo.com/2092236 adultsCount=2&arrival=2020-10-27&departure=2020-10-31&unitId=2656769brbrSparkling clean and beautifully remodeled 2Bd/2Ba vacation home that features OPEN WATER views with great boating access to the ocean or gulf! This home is fully furnished will all the amenities for an over the top vacation experience. This waterfront paradise features a 35' concrete seawall with cleats, dock posts, fish table and BBQ grill to cook your catch! Main living room offers high ceilings with awesome views of the water and leads to a spacious covered porch overlooking the water. This home is designer decorated with lovely accents and decor throughout. Kitchen features clean and white kitchen cabinets with full line of appliances and granite countertops. Living room features lots of comfortable seating with queen sleeper sofa, love seat and 2 comfortable chairs with a large flat screen television with full expanded cable and you will enjoy splendid water views. Master bedroom features a king size bed with lots of closet storage and full size private bathroom. Guest bedroom features a queen bed with closet storage and access to the hallway full bathroom. Additional amenities include central air conditioning, heat, dishwasher, microwave, washer, dryer, tile floor, BBQ grill, fish table, expanded cable, ceiling fans, patio furniture and covered porch. You'll set your mind at ease when you stay at this beautiful home in the Florida Keys!br7 day minimum during lobster season. No Smoking, No Pets. There is a resort usage fee of $125 payable upon arrival at entrance at security gate to Venture Out.brbrRental agreement is agreed upon at booking and pre-registration form of guests must be completed prior to stay or when checking in at the security gate.brbrThe community will be limiting overflow parking lot spaces (which is at a nightly fee to guest). They will only be able to accommodate for one spot for an extra car or boat trailer if available; do know there's a driveway at the home to park a car, this is only in regards to extra cars or boat trailers.brIf no spots are available guest will need to find a spot outside of the park. We understand this is a great inconvenience so we have negotiated a spot for a trailer at a nearby marina at a rate of $20 a day, if interested please let us know so we notify the marina. Thank you

Tropical Island Paradise W / Open Water Views!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$274.15

COASTAL OASIS is just for you. This three-bedroom two-bath canal-front home offers a comfortable base for your Keys adventures. The living room, dining room, and kitchen are all found in a large open area adjacent to the large screened porch. The kitchen is fully equipped. Amenities include a washer/dryer, TV, central A/C, dishwasher, and barbecue grill. For sleeping, there is a Queen in 2 bedrooms and 2 full beds in the 3rd one. For the boaters and fishermen, there is a concrete dock on the canal. Access to the Atlantic, coral reefs, Gulf Stream, Gulf, and backcountry is easy. Located nearby are restaurants, groceries, fuel and bait, convenience stores, banks, post offices, and more. Within an easy drive, there is much more to be found, Key West with all it offers, dining, shopping, history, and the like, is 23 miles to the south. Big Pine Key with its natural attractions is 7 miles north. Just a bit further north is the world-class beach at Bahia Honda State Park. The Miami airport is a three-hour drive. This is a nonsmoking home. THIS HOME IS A 28 DAY RENTAL PER MONROE COUNTY CODE. This home is a 28 day rental per Monroe county code.br

Coastal Oasis, Canal front

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$487.3

Oceanfront Dream Home - VO048br2Bd/2Ba OCEANFRONT 45' SEAWALL! br This BEAUTIFUL 2Bd/2Ba OCEANFRONT with endless ocean views features a 45' SEAWALL! Wake up to beautiful sunrises and the Atlantic Ocean every morning. heavy duty padded dock posts, cleats and extension swim ladder with over 4' controlling depth at the seawall, so a larger boat is welcome. A bright and spacious living area features oversized windows to bring the outdoors. The dining room offers seating for 4, kitchen features a full line of appliances with white kitchen custom cabinets and Corian countertops. A large island countertop makes the perfect place to serve or entertain your family and friends. The living room leads to a covered porch overlooking the ocean. This welcoming property features 2 queen bedrooms, perfect for guests to unwind after a day of exploring. With amenities like WiFi, a washing machine, and AC, your stay will be nothing short of enjoyable. Make your holiday one for the books with a stay at our place.SECURITY 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**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****

Oceanfront Dream Home - VO048

Cudjoe Key, Florida, United States

Bed

Bath

4

Sleeps

$504.28

This luxurious Cudjoe Key vacation rental home, located directly on a sandy beach overlooking the crystalline Atlantic Ocean, is part of Sunrise Beach Resort, an exclusive gated community with only 10 other homes. In addition to high end furnishings in the living area, it features two tastefully decorated master suites, each with a full private marble bathroom. You can soak up the sun on the beach, on the pool deck, or enjoy the shade under the tiki hut by the sparkling, heated/cooled swimming pool located directly beside the house, also overlooking the ocean. Lounge in your private hammock or enjoy a drink in the double swing underneath our home which overlooks the beach. Or, you can soak in the gorgeous tropical landscaping and cool breezes on the comfortable, luxurious furniture located on the home’s deep shaded lanai, which includes a flat screen TV adjacent to the beach. Breathtaking views of the blue green ocean, Cudjoe Bay, and the sunrise and sunset can be seen from every room and from the two decks accessible from both bedrooms, the dining room and the living room. brbrIf you are looking for a lower keys short or long term rental, Cudjoe Key has a reputation as the best place to stay on the water in the keys. Your boat, up to 25 feet, can be kept for free at the stationary or floating docks in the calm waters directly behind our house, while your boat trailer can be stored close by, at no cost to you. Or you can rent a boat and have it delivered to the dock behind our home. Looe Key and American Shoal Reef can be seen from the house where you’ll find the most beautiful snorkeling and diving reef in the keys, along with the best fishing. Their off-the-beaten path location guarantees a thriving ecosystem. You can fish right off the end of the dock or kayak in the crystal clear, calm waters in Cudjoe Bay directly behind our house (kayaks are included). Venture out to experience the history and action in Key West located only 20 miles away, or explore dozens of nearby islands and a trove of nature preserves by land or sea. Ours is the perfect Cudjoe Key vacation house rental located near Big Pine Key, Summerland Key, Sugarloaf Key and Key West, Fl. brbrIn the immediate area you’ll find several good restaurants. For example, you can take your boat or catch a free ferry to Little Palm Island where you can enjoy lunch or dinner at a top ranked best restaurant in the world. Several other excellent restaurants in the keys are located on or close to Cudjoe Key. A gym/wellness center and Cudjoe Garden’s Marina, a full service marina, are located one mile away. Fishing, snorkel, dive or sightseeing trips can be arranged through Nothing Better Boat Rentals on Cudjoe Key, and they can either captain a rental boat for you or have one delivered to our docks. The only 18 hole miniature golf course in the keys is located five miles away. Pack a lunch and spend the day at Bahai Honda State Park, voted the #1 beach in the U.S., which is only a 20 minute drive away. The Dolphin Research Center, which offers dolphin encounters, is another area attraction. brbrWe provide bikes, kayaks, a corn hole game, beach chairs, a beach umbrella, beach toys and towels, bocce ball, and a cooler for your enjoyment. We are always adding extra toys and oftentimes have a clear see-through kayak and stand up paddle boards available as well. Relax on our hammock or on our swing overlooking the beach. Four bikes are available for you to enjoy a leisurely bike ride down the scenic tree lined bike path, accessible directly across the street from Sunrise Beach, which traverses Cudjoe Key and continues all the way to Key West. Cudjoe Bay is the perfect calm place to kayak and enjoy the clear water. Our home has something for those who want to relax and enjoy the views off the beaten path, and as well as for those who wish to explore all the keys have to offer!brbrThis casually elegant home provides:br* High ceilings with crown moldingbr* Gourmet kitchen with stainless appliances, granite countertopsbr* Keurig for individual pods or full pots of hot beverages br* Kitchen stocked with a blender, spices and staplesbr* Private full marble bathrooms in each bedroom, plus a full marble bathroom next to the living roombr* Shampoo, conditioner, and body wash provided in all 3 bathroomsbr* Jacuzzi tub in one master bathroom, walk in showers in the other two bathrooms.br* Plantation shutters in bedrooms and bathrooms.br* 4 flat screen HD TV’s br* SMART TV with DVRbr* Wi Fi Internet br* Private hammock br* Large selection of books, including local guides, and gamesbr* Luxurious decor and furnishingsbr* Covered parking for 2 vehicles br* Large walk in closets with round windowsbr* Pack 'N Play Crib, baby linens and bedrailsbr* Gas grill br* Bikes (4), with helmetsbr* Beach chairs, umbrella, cooler, corn hole, bocce ball, beach toys br* Fishing poles, tackle box, snorkeling finsbr* Kayaks (2 singles, 1 double), with life vests, and paddlesbr* Flat screen TV overlooks the luxurious outdoor furniture on the shaded lanai underneath the house overlooking the beachbr* Private swing overlooking beach br* Pool, beach, and dock are shared with only 10 other homes in our small gated community. brbrThis is the perfect vacation home for families or couples looking for relaxing ambiance in an opulent tropical hideaway and for those who want it all – beach, pool, boat dock, and stunning views in order to experience the 'real' Florida keys. brbrbrbrbrbrbrbrbrbrbrKeywords: Oceanfront, Beachfront, Gated Community, Boat Dockage, Heated Pool, Kayaks, Bikes, Cudjoe Key Cottages, Fishing, Corn Hole, Hammock, Snorkeling, Views

Luxurious Oceanfront Home on Beach, Pool, Dock, Kayaks, Bikes, Amazing Views!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$400.0

VO074brCanal Front Open Water 35' Seawall brStilt 2Bd/2Ba Covered Porch brSimply elegant describes this 2 Bedroom / 2 Bath canal front stilt home only 3 lots from open water! This home features a 35' concrete seawall with access to the Gulf and Ocean! Dock amenities include dock posts, cleats and fish cleaning table. The upper porch as comfortable lounging furniture overlooking the water. Interior features tile flooring, living room flat screen TV, full line of appliances, washer, dryer, ceiling fans and central A/C. Sleeping accommodations include a King size bed in the Master bedroom and a private bathroom, Guest bedroom as 2 twin beds that can be pushed together as a king. Master bedroom with sliding glass door provides access to a balcony, flat screen TV and private full bath. Downstairs features outdoor shower, access to storage room and covered parking. Additional amenities include in home FREE WIFI, basic cable, gas grill, bait freezer an assortment of bicycles.br SECURITY DEPOSIT REQUIRED, NO SMOKING, NO PETS,br7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL,brOVERFLOW PARKING S NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brVO REGISTRATION FEE -**EFF 7-1-23 new fee is $125**DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.

Beach house in the Keys - VO074

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$532.58

This 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key private heated salt water swimming pool, shaded hang out area, ping pong table, corn hole game. The pier, gazebo, kayaks and kayak launch area is shared with one other home, Latitudes. You can dock your 24' boat at the pier. The water is shallow getting out to the channel with about a 2' draft.brbrYour property manager lives nearby and is available if you have any requests during your staybrbrQuite/peaceful neighborhoodbrbrYou will be provided with check in instructions prior to your arrivalbrbrThis 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key has a large, heated swimming pool with shaded hang out area, ping pong table and corn hole game. 1 Double and 2 single kayaks provided. This home has a boat Foch that is shared with The Latitudes home Ultimate location only 20 minutes from Key West and 20 minutes to Bahia Honda State Park. This is a vacation experience you will remember.br*Master Bedroom: 1 King bedbr•King Bedroom: 1 King bed br•Queen Bedroom: 1 Queen bed br•Living Room: Queen sleeper sofa, Flat screen Smart TVbr•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. We do not supply laundry soap. br•Outdoor Features: Propane BBQ, Hammock br•Boat Dockage: Tall pier for boats up to 24'. The dock is shared with Latitudes home guests. 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 TV's br•Location: 20 minutes from Key West, 15 minutes from Bahia Honda State Park. br•Pool: 10X30, heated Salt water poolbr Square Footage of House: 1456 sq ftbrbrCancellation: 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. brbrbrNon-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.brbrBus service available. It is recommended that you rent 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.

Blue Palms w/boat dock and saltwater pool.

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$638.79

Oceanfront home with private pool, boat dock, kayaks, and private beach brbrTropical Paradise has been a popular and romantic vacation rental getaway since 2003. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' boat allowed) screened in porch for dining There are 2 king bedrooms, 3rd bedroom has a queen with trundle 2 1/2 bath. This home has an open floor plan and recently remodeled kitchen.brbrOur offices are located about 6 miles from this home. we are available 24 seven for any issues you may have. we respect our guest space and will let you know if we need to be on property for any reasonbrbrbrbrQuiet residential neighborhoodbrbrEntire homebrbrYou will be provided with check in instructions prior to your arrivalbrbrThis adorable home has 3 bedrooms and 2 1/2 baths. A screened in porch with walkout to the dipping pool.brThe pool deck is fully fenced for safety and for your pet. Banana trees and coconut trees give this home that Tropical VibebrbrUber, 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.

Tropical Paradise - Ocean front with swim spa

Cudjoe Key, Florida, United States

3

Bed

Bath

8

Sleeps

$431.25

You're in the tropics... listen to the waves, rest, relax or fish, kayak and snorkel, if you wish to lose a few pounds. Three bedroom, two bath home, with direct ocean access, boat parking at the back door. Sunrise view, ocean breezes. Fully furnished, linens, cable/internet. This home is on a compound, we also have several one bedroom units as well as 2 bedroom. The perfect spot for large groups! Square Grouper restaurant and bar in the is down the street. Lower Keys Shuttle to Key West just steps from the home. Come and stay with us, you're sure to have a wonderful vacation.

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Cudjoe Key, Florida, United States

3

Bed

Bath

6

Sleeps

$206.57

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Endless Summer Retreat, a dog-friendly 3-bedroom, 2-bath canal front home located in the desirable Cudjoe Gardens! brbr brbrPerfect for boating enthusiasts and pet lovers alike, this peaceful getaway offers deep water dockage and easy access to the Atlantic and Gulf via the scenic Bow Channel. The nearby Cudjoe Gardens Marina, with its marina store and boat ramp, adds extra convenience for those looking to make the most of their time on the water. Inside, the home features a modern coastal design with spacious living areas, a fully equipped kitchen, and comfortable bedrooms to ensure a relaxing stay. Step outside to the waterfront patio where you can enjoy alfresco dining, sunbathing, or simply relax by the water. The deep water dock makes it easy to embark on fishing, snorkeling, or boating adventures directly from the house. Located just 30 minutes from both Key West and Marathon, Endless Summer Retreat is close to the vibrant attractions and dining of the Florida Keys, while providing a quiet escape when you want to unwind. Whether you're planning a boating trip, a family getaway, or a vacation with your furry friend, Endless Summer Retreat is the ideal destination for a memorable Florida Keys experience! brbr brbrSLEEPS MAXIMUM OF 8 GUESTS: brbr brbrBedroom 1: King Bed, En-Suite Bathroom, Smart TV (no cable/satellite) brbr brbrBedroom 2: King Bed, Smart TV (no cable/satellite) brbr brbrBedroom 3: King Beds brbr brbrLiving Room: Sofa W/ Pull-Out Queen Bed, Loveseat, Recliner, Smart TV (no cable/satellite) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- 80' of Seawall & 30' of Dockage (boat lift not available for guest use) brbr brbr- Fish Cleaning Station with Water brbr brbr- Bait Freezer brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Parking for a maximum of 4 vehicles (including boat trailers) on the property. (Up to two in the driveway and up to two in the yard). Recreational Vehicles may not be parked on the property. brbr brbr- Linen's and towels provided brbr brbr- Cudjoe Gardens Marina (.3 miles by boat & .2 miles by car) w/ Marina store and boat ramp brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrPet Policy: Up to one friendly and well-behaved dog will be considered with a $10/night pet fee. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit household pet information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrBoating & Dockage Advisory: Due to bridges and varying water depths, it is your responsibility to ensure that your boat can safely navigate local waters, access the canal, and fit the listed dockage before booking. While we are happy to provide general information based on our knowledge of the area, guests must exercise extreme caution when boating and ensure all activities comply with local regulations. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of our guests and property, two exterior security cameras monitor the front and rear of the property. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

Endless Summer Retreat: Dog-Friendly 3BR Canal Front Oasis, Dockage & Easy Atlantic/Gulf Access

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$266.58

Welcome to Unit 28 at Venture Out, your cozy coastal retreat tucked inside the sought-after gated community on Cudjoe Key, FL. This charming two-bedroom, one-bath vacation rental is ideal for families or small groups seeking sunshine, serenity, and a taste of the Keys lifestyle. Step inside and feel right at home in a thoughtfully furnished space designed with comfort in mind. The primary bedroom features a queen bed, while the second bedroom offers a fun and functional twin bunk bed—perfect for kids or extra guests. The bathroom includes a large tiled walk-in shower, providing a comfortable and convenient space to refresh after a day of island adventures. The living area invites you to kick back and relax, complete with a full-sized couch and two cozy recliners—perfect for movie nights or quiet afternoons. A fully stocked kitchen and dining area with seating for four make it easy to prepare and enjoy home-cooked meals after a day of exploring. There is a Mr. Coffee and Keurig coffee maker at this home for you to enjoy your favorite brew. Outside, you'll find a private patio outfitted with outdoor furniture and a gas grill, creating a great spot for evening cookouts and laid-back conversations. Just a short stroll to the community pool, this home offers both privacy and convenience. Additional amenities include an in-unit washer and dryer, free Wi-Fi, and access to all the fantastic features of the Venture Out community. Whether you're here to explore the turquoise waters, fish the backcountry, or simply soak up the sun, Unit 28 is your perfect Keys hideaway.brThis is a pet friendly home that allows up to 2 dogs with a $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 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! Whether 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 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. Main 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.

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$378.41

SEA ESCAPEbrThis two story home with breathtaking full views of the crystalline Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community with only 10 other homes. Just steps from the house is the stunning oceanfront heated swimming pool and charming Tiki hut, or enjoy the gorgeous tropical landscape and Keys breezes from your own private hammock and manicured space. Ocean sunrise and sunsets can be viewed from every room and from two decks. WiFi-enabled, this immaculate home boasts two master suites, both with a master king bed; both have a private bathroom with private full bath, and access to the second floor balcony. Downstairs you’ll find a third full bath with a shower, a 40'' HDTV, a full sleeper sofa, dining table for six, a breakfast bar, a second balcony with lush foliage and views of the Atlantic Ocean, washer/dryer, and a fully equipped gourmet stainless steel kitchen. The ground floor offers parking for 2 cars, an entertaining space with table and chairs, and a grill. br*If you bring a pet without our consent you will Forfeit your FULL security deposit. brbr Your boat, up to 25 feet, can be kept on one of two floating docks directly behind the house. Looe Key and American Shoal Reef are visible from the house where you’ll find the most beautiful snorkeling and diving in the Keys, along with the best fishing; or catch fish right off the end of the dock. Snorkel or kayak in the mirror clear, calm waters of Cudjoe Bay a few yards from the house. Location is everything and Key West is only 17 miles in one direction and world famous fishing and snorkeling destination Marathon Island 25 miles in the other.brbrIn the immediate area, you’ll find several excellent “Keys” restaurants, a gym/wellness center, and Cudjoe Garden’s Marina, a full service marina offering boat rentals, as well as fishing, snorkel, and dive trips. The only 18-hole miniature golf course in the Keys is located five miles away. Smather’s Beach and the Dolphin Research Center, which offers dolphin encounters, are other area attractions. Spend the day at Bahia Honda State Park, voted the #1 beach in the U.S., or catch a free ferry to Little Palm Island where you can enjoy lunch or dinner at the #3 ranked best restaurant in the world, both only minutes away.brbrBeach, pool, dock, privacy, and views - in a tropical setting with quick access to all the fun that the Keys has to offer. This is the perfect home for families or couples looking for more than a vacation: a “real” Florida Keys experience! brbrbrHighlights of this casually elegant home include:brbr* Bamboo wood floorsbr* Gourmet kitchen with stainless appliances, granite countertopsbr* 3 full private bathrooms one in each bedroom, plus a full bathroom downstairs br* washer/dryer/dishwasherbr* 2 king size beds, plus full sleeper sofa in the living room. br* 2 private balconies with furniture and bistro setbr* private shaded hammockbr* 3 flat screen HD TV’s - 32” in each bedroom and 40” in living roombr* Wi Fi Internet br* Covered parking for 2 vehiclesbr* Large walk in closets br* Gas grillbr* patio furniture br* Kayaks (2), life vests, and paddlesbr* Fully stocked linens, bath, and beach towels, beach chairsbrbrbrbr

WEEKLY RENTAL Florida Keys Pool & Waterfront Vacation Rental 108

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$365.63

Dock your boat behind the house and enjoy open water view. Located in Cudjoe Key, this newly renovated house offers 2 bedrooms - one with a king bed, full bed, and twin bed. The property also features 2 full bathrooms and an outdoor shower. In addition, there is an extra living space with a cozy murphy bed. Our home is perfect for your family get away or a couples retreat. Home comes with 2 kayaks and 2 bikes. The gated community offers pool, beach area, hot tub, pickle ball, playground area, basketball and a recreation room.brTHERE IS A $125 RESORT FEE DUE AT THE GATE UPON ENTRY.

35' dock completely remodeled Home

Cudjoe Key, Florida, United States

Bed

Bath

6

Sleeps

$585.17

Open water home on the south side of Cudjoe Key, this home is that special place where you can get away from it all. Sometimes if you are lucky, you might catch a glimpse of dolphins feeding in the emerald waters. The expansive waterfront features an Oceanfront observation deck, tropical gardens, and a very private beach area that is perfect for kayaking and basking in the sun. Adjacent is the open pool, hot tub, and surrounding decks as well as the sheltered Tiki bar and entertainment area. Within the expansive home, you will find a huge open great room with a newly redesigned kitchen featuring high-end appliances and granite counters, all opening onto a full-length screened porch with spectacular open water views. For sleeping, you will find a king bed in the master suite, with a queen and two twins in the other two bedrooms. Amenities include a fully equipped kitchen, 4 TVs, CD, stereo, DVD, wireless high-speed internet access, barbecue grill, hot tub, washer/dryer, 2 kayaks with life-jackets, waterside entertainment area with a large bar, seating areas, and privacy. For boaters and fishermen, there is a boat dock on the adjacent canal and the reef and Gulf Stream are within five miles, with Gulf and backcountry access. You will find all your shopping needs within a short drive, while Key West and all its unique offerings are just 23 miles away. The Miami Airport is about a 2.5-hour drive. This is a designated nonsmoking home. Ask about our pet policies. THIS HOME IS A 28-DAY MINIMUM RENTAL PER MONROE COUNTY CODE.

Oceanfront Seclusion, Oceanfront with pool

Cudjoe Key, Florida, United States

3

Bed