Vacation Home Rentals By Owner In Cudjoe Key, FL

This is a beautiful newly built 4 bedroom, 3 bathroom house located on a cul-de-sac in quiet Cudjoe Gardens. The house includes a heated pool/jacuzzi, large 110 ft. dock with fish cleaning station and is equipped with water and electric, laundry room, and even an ice machine! The spacious Master Bedroom includes a walk-in shower, jacuzzi tub and easy access to the pool. Bedroom #2 has a queen bed and private bathroom. Guest bedroom #3 includes two twin beds. Guest Bedroom #4 has a king bed, spacious closet and direct access to the pool. brThe kitchen is fully equipped with a walk-in pantry and plenty of room for you to cook up the fresh catch of the day. For all you wine lovers there is a wine fridge/bar located adjacent to the kitchen. There is plenty of parking for boat trailers and extra vehicles. Just down the street is a marina with a boat ramp for your convenience. Whether you relax by the pool with a tropical drink in hand or venture out on the water from your boat lift for some fishing or sunset cruise, you are sure to enjoy your stay here. Not to mention, the location of this beautiful property is great…it’s only 20 miles to Key West!

Gorgeous New 4/3 With Heated Pool/Spa And Large Deep Water Boat Dock

Cudjoe Key, Florida, United States

4

Bed

3

Bath

8

Sleeps

$264.42

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.

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

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$214.13

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.

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

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$492.47

***NEVER RENTED BEFORE!!brBe one of the first to stay in our newly renovated home! With a 35' Seawall for docking your boat or water toys, this can be your 2 bedroom 2 bath waterfront getaway in Cudjoe Key!! Ocean views from every room in the house. Located in the lower Florida Keys at MM# 23 only 19 minutes to Key West. Our home is in the gated community of Venture Out. *Sleeps 6 guests*2 Full Bath* WiFi* * TV * A/C & heat *Fully equipped kitchen*Dishwasher*Stove & self clean oven* Refrigerator/freezer with ice maker*Microwave* Blender* Toaster oven* Service for 12* All eating utensils, bake & cookware*Keurig & 12 cup coffee maker* New King, queen & queen sofa sleeper*Brand New Amenities including propane grill, 4 Bikes & 2 two-person Kayaks **COMMUNITY AMENITIES: Olympic size heated Pool, kiddie pool, HotTub, Marina, Boat Ramp, fuel docks, fish filet station, boat wash down station, Children's playground, Convenience Store, Recreation hall with darts, pool table & ping pong. Daily activities-- pick up monthly schedule at the guard booth.Tennis, Pickleball, basketball, Bocce ball, library, church services, post office. Too much to list!br**FREE PARKING FOR 1 VEHICLE IN OUR DRIVEWAY br***WE ARE SMOKE FREE AND PET FREE***br***ONE TIME ENTRANCE FEE $125. PAID UPON ARRIVAL AT GUARD BOOTH OR REGISTRATION OFFICE. ***br*Parking for 1 additional car and/or 1 boat trailer in the overflow parking lot for an additional fee. Overflow parking is on a first come first served basis & is not guaranteed. There are 2 outdoor cameras. 1 facing the driveway and 1 facing the dock.

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

Cudjoe Key, Florida, United States

Bed

Bath

6

Sleeps

$945.0

Welcome to The Grand Tiki Estate — your private slice of paradise in the heart of the Florida Keys! This stunning waterfront retreat on Cudjoe Key offers the perfect blend of tropical island charm, modern luxury, and breathtaking open-water views that will make you want to book the moment you arrive.brbrFrom the moment you step onto the spacious property, you’ll be surrounded by swaying palms, sparkling turquoise waters, and panoramic vistas stretching across Cudjoe Bay to the Atlantic Ocean. Whether you’re sipping coffee on one of several breezy balconies, lounging poolside under the sun, or relaxing in the tiki hut with a cool drink, every corner of this home is designed for island living at its finest.brbrOutdoor Paradise - brThis waterfront oasis truly shines outdoors. Enjoy a large coral-shaped in-ground pool with spa, fully fenced for privacy and safety, plus a sandy beach area perfect for soaking in the Keys vibe. The private dock extends into crystal-clear water—ideal for boating access, fishing, or launching a paddleboard for a sunset glide. Lush tropical landscaping surrounds the spacious lot, creating a secluded, resort-like feel.brbrBright, Spacious Island Living -brInside, the home features an open-concept layout with plenty of space for gathering and relaxing.brThe updated kitchen boasts high-end appliances, a gas cooking stove, and a large island with seating—perfect for entertaining. The living and dining areas offer comfortable furnishings, a fireplace, dining for six, and open directly to a balcony where you can enjoy sweeping water views and gentle ocean breezes.brbrLuxurious Bedroom Retreats -brThe spacious primary suite is a true sanctuary, featuring a king bed, fireplace, seating area overlooking the water, private balcony access, walk-in closet, and a spa-like bathroom with double sinks, a large shower, and a jetted garden tub.brThree additional bedrooms provide comfort and flexibility for guests, including multiple balcony access points, sitting areas, and a bonus trundle bed space—perfect for families or groups.brbrIdeal Location -brYou’ll enjoy peaceful island seclusion while still being just a short drive from the world-famous dining, nightlife, and entertainment of Key West.brbrWhether you’re planning a relaxing getaway, boating adventure, or unforgettable family vacation, The Grand Tiki Estate delivers the ultimate tropical escape with space, luxury, and unbeatable waterfront views.

The Grand Tiki Estate - Private Dock, Pool & Endless Ocean Views

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$544.46

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #111 and I also rent adjacent homes 107 and 109 in case you need more than one. We are 80 feet from the water`s edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can boat, get sun, fish or fish from the docks. Key West is 17 miles away.brbrThis casually elegant home has: br* high ceilings with crown molding and four ceiling fans.br* a gourmet kitchen with stainless appliances and granite countertops.br* two master suites with king beds and full private baths.br* a sleeper sofa in living room downstairs with a third full bathroom.br* 3 flat screen HDTV’s with cable and WIFI.br* covered parking for 2 vehicles.br* cooler, beach toys, fishing poles, kayaks, bicycles, and paddleboards.brbrThis is the perfect stand-alone vacation home for families or couples looking for relaxing ambiance in tropical setting. And for those who want it all – history, nightlife, beach, pool, boat dock, kayaks and views.brbrYour boat, up to 25 feet, can be kept at the dock for your entire stay in the calm waters directly behind the house. I pay for you to store your trailer off-site.brbrGated Community of 11 homes, which are all used exclusively as vacation rentals.brbrLooe Key and American Shoal Reef can be seen from the house where you’ll find the most beautiful snorkeling and diving reefs in the keys along with excellent fishing. Fish or kayak right off the dock or you can venture out to experience the history and action in Key West located only 17 miles away. In the immediate area you’ll find several very good fine dining and casual restaurants, grocery, liquor store, and Cudjoe Garden’s Marina, a full-service marina offering boat rentals.brThe $250 cleaning fee is not collected with your reservation but is required. You are asked to leave it inside the home upon departure for the housekeeper. To be clear, this $250 is in addition to the other rental costs and taxes that are collected from you upon booking.brbrDuring high seasons, guests must typically check in or out on a Saturday or Sunday, unless stay is more than 10 nights. Exceptions are possible upon request. brbrTRAILER AND VEHICLE PARKING: There is space under home for two standard vehicles. Campers, travel trailers, recreational vehicles, trucks with dual rear wheels and trucks larger than one ton are prohibited from the community. Please park under home and not to the side where it will block your neighbor. I pay for my guests to store their boat or boat on trailer at nearby facilities during their stay. If you will be bringing your boat, or PWC you must tell me now along with your boat description including length. brBoats, PWC and trailers are not permitted to be stored on premises except for day of arrival until noon the next day, and for last 24 hours before departure. Vehicles and trailers may not park on grass or hinder emergency personnel or block any guest’s vehicular access to their home. brbrCONDITION AND USE OF PROPERTY: The Property is provided in “as is” condition. Owner shall use its best efforts to ensure the operation of all amenities in the Property, such as internet access, cable TV access, pool, recreational equipment as applicable. Owner shall not be held responsible for such items failure to work, but will make every effort to correct any issues as reported as quickly as possible. Guest shall use the Property for residential purposes only and in a careful manner to prevent any damage or loss to the Property and keep the Property in clean and sanitary condition at all times. Guests shall refrain from loud noise and shall not disturb, annoy, endanger, or inconvenience neighbors. Guests shall not use the Property for any offensive or unlawful purposes and shall abide by association rules, and not commit waste or nuisance about the Property. brbrExtra fees up to $100 may be charged for excessive cleaning. This fee may apply for failure to follow checkout rules including emptying all trash, damaged or missing items including towels and furniture left out of place.brbrRISK OF LOSS AND INDEMNIFICATION: Guest agrees that all personal property, personal effects and other items brought into the Property by Guest or their permitted guests shall be at the sole risk of Guest with regard to any theft, damage, destruction or other loss and Rental Agent shall not be responsible or liable for any reason. Guest agrees to indemnify and hold harmless Rental Agent and their agents, owners, successors, employees and contractors from and against any costs, damages, liabilities, claims, legal fees and other actions incurred by Guest, their permitted guests, or agents, representatives or successors of Guest due to any claims relating to destruction of property or injury to persons or loss of life sustained by Guest or family and visitors of Guest in or about the Property.brbrRELEASE: Guest acknowledges that use of amenities may be dangerous, particularly with regard to children, and such use is at the Guest’s own risk. Guest waives and releases any claims against Rental Agent, the Property owner and their successors, assigns, employees or representatives for any injuries or death that may be sustained by Guest or their permitted guests or invitees on or near or adjacent to the Property, including any common facilities, activities or amenities including but not limited to pools, decks, kayaks, paddleboards, bicycles, snorkeling equipment and floats. Guest agrees to use any such facilities or amenities entirely at the Guest’s own risk and responsibility. brbrREFUNDS: If evacuation, or delayed arrival, due to a named storm is necessary, the unused portion of Guest payments will be refunded.brbrSMOKING AND PET POLICIES: Home is pet free and non-smoking both inside the home and on balconies. brA minimum fee of $250 will be charged for violation of either policy.brbrSUNRISE BEACH COMMON AREA RULES:br1. Use of common area including pool, beach, dock and TIKI hutbra. Limit noise to conversation level after 10PM brb. No loud music or boisterous noise at any timebrc. No glass containers permitted brd. Children must be supervised at all timesbre. No running, rough play or divingbrf. Animals are not allowed in the poolbrg. No smoking unless downwind from other guests and homesbr2. Trash and Recycling:bra. All trash should be disposed of from homes and common areas in closed 13-gallon bags and placed inside the dumpster. brb. All recycled goods (cans, bottles, cardboard) should be placed loose inside the blue recycle cans WITHOUT bagging. br3. Use of marina and boat docksbra. Drive on docks and all mooring positions are on a first come first serve basis. There is no reserving of dock space. Drive on docks for boats 17 feet and smaller.brb. One motorized watercraft up to 25 feet in length is permitted per home with beam under 9 feet. Exceptions can be made for additional personal water craft based on available space.brc. Please be mindful of depth and stay inside of marker buoys.brd. Fish cleaning station is provided. Please hose any fish remains into bay and do not place into trash.br4. There are no common area spaces for parking. brContact for Questions or Issues: Please see home info notebook inside the home.

Oceanside home, dock,kayaks,bikes,pool,fishing,111

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$456.98

Upscale Ocean Vue Retreat with breathtaking views from Sunrise to Sunset! This waterfront gem offers amazing views and is the perfect getaway for your next vacation in Paradise. Quick access to the Gulf of Mexico and the Atlantic Ocean from your seawall. This 2 bedroom, 2 bathroom vacation home is equipped with everything you need to unwind and relax. Offering a high end kitchen, full line of appliances, three smart tv's and a 35-foot seawall to dock your boat. Gated community with Oceanfront Heated Saltwater Pool, Marina with Convenient Store, Fuel Dock and Boat Launch. Pickleball, tennis, basketball and bocce courts and so much more. VO COMMUNITY REGISTRATION FEE OF $125.00 IS DUE UPON ARRIVAL IN CASH OR CREDIT CARD ONLY.

Ocean Vue in Cudjoe Key 469

Cudjoe Key, Florida, United States

Bed

Bath

4

Sleeps

$182.91

2 Bedrooms/2 Bathroom home ready for move in May 2026. Property has an open concept living space with tiling throughout, shower and soaking tub. No pets preferred, possible on approval of breed with non-refundable $250 pet fee. (Small pets only, call please) Utilities (water and electric) are tenant responsibility. First and last months rent and security deposit to move in. Prefer 6 month rental, but negotiable. Serious inquiries only - br2 good size bedrooms both with queen beds and one with an on suite. 2nd bath has a tub with a shower. Fully furnished including fully equipped kitchen flowing into a nice dining nook, large, furnished screened in porch and gas grill. Tommy Bahama furnished living room with TV and nice natural lighting. Downstairs has a nice deck walkway leading to dock. Dock has ladder for swimming in the canal.br This is located Waterfront on a clean boating canal with direct access to Cudjoe Bay. It is in a nice neighborhood with good neighbors. I love the sunny frontage and sitting on the screened in porch with fans on low and the sun filtering through the sun shades; paradise! Under the home is a Tiki Bar and seating area. 2 Kayaks, a paddle board and cornhole game included with no extra charge !brBoat Lift requires a separate rental contract

SHORT TERM RENT WITH 10k BOAT LIFT Avail from 5/1/2026 for 5-6 months

Cudjoe Key, Florida, United States

Bed

Bath

10

Sleeps

$269.36

Casa Mojito – Your Slice of Paradise in the Lower Keys. Escape to this beautifully landscaped 3-bedroom, 2-bath canalfront retreat in Cudjoe Key, where boating, island living, and relaxation come together perfectly. With room for up to six guests, Casa Mojito is ideal for families, couples, or friends looking for an unforgettable Florida Keys getaway.brLocated on a quiet canal, the property features 30 feet of wooden dock frontage with six secure dock posts—perfect for boats up to 30 feet. After a day on the water, rinse off in the private outdoor shower, clean your catch at the dockside fish cleaning station, and store bait in the dedicated freezer. Unwind with a drink in the covered hammock, fire up the Everdure grill, or enjoy island breezes from the screened-in porch with outdoor dining for four and cooling ceiling fans overhead.brInside, you'll find a bright, modern coastal design adorned with local Key West art, creating a true island vibe. The home offers a fully equipped kitchen and dining for six, plus a two-seat breakfast bar, smart TVs in the living room and all bedrooms for easy streaming, a king bed in the primary suite, a queen bed in one guest room, and two twin beds in the other. The updated en-suite bathroom in the primary suite adds comfort, and additional conveniences include a private downstairs renter's closet with a beverage fridge, bicycles and two kayaks (available with signed waiver), and keyless entry. This 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. brThere is a Mr Coffee 12 cup drip Coffee Maker at this home for you to enjoy your favorite brew.brWhen you're ready to explore, you'll be just minutes from Key West and close to beloved local favorites like 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 here to fish, snorkel, boat, or simply soak up the sunshine, Casa Mojito delivers the perfect blend of comfort, style, and adventure.brThis is a 27-night minimum rental per county ordinance. Proper county and state taxes are collected regardless of booking platform. The renter must be 25 years of age or older, and overnight occupancy is limited to a maximum of six people, with all guests registered with the Rental Manager. There is a security camera at the outdoor front entrance and one in the owner's secure storage space. Smoking is not permitted. This home is pet friendly, allowing up to two dogs with a non-refundable pet fee of $250. Utilities are included within reason, but any water usage over $250 will be billed to the guest. A $55 Damage Waiver Insurance is required to protect both guest and owner. All reservations are subject to final approval by the local Rental Manager, and online bookings are accepted with Rental Manager approval 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.

Tropical 3BR on Canal – Dock for 30' Boat, Outdoor Shower, Bikes, Sleeps 6

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$520.85

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #109 and I also rent adjacent homes 111 and 107 in case you need more than one. We are 80 feet from the water`s edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can boat, get sun, fish or fish from the docks. Key West is 17 miles away.brbrThis casually elegant home has: br* high ceilings with crown molding and four ceiling fans.br* a gourmet kitchen with stainless appliances and granite countertops.br* two master suites with king beds and full private baths.br* a sleeper sofa in living room downstairs with a third full bathroom.br* 3 flat screen HDTV’s with cable and WIFI.br* covered parking for 2 vehicles.br* cooler, beach toys, fishing poles, kayaks, bicycles, and paddleboards.brbrThis is the perfect stand-alone vacation home for families or couples looking for relaxing ambiance in tropical setting. And for those who want it all – history, nightlife, beach, pool, boat dock, kayaks and views.brbrYour boat, up to 25 feet, can be kept at the dock for your entire stay in the calm waters directly behind the house. I pay for you to store your trailer off-site.brbrGated Community of 11 homes, which are all used exclusively as vacation rentals.brbrLooe Key and American Shoal Reef can be seen from the house where you’ll find the most beautiful snorkeling and diving reefs in the keys along with excellent fishing. Fish or kayak right off the dock or you can venture out to experience the history and action in Key West located only 17 miles away. In the immediate area you’ll find several very good fine dining and casual restaurants, grocery, liquor store, and Cudjoe Garden’s Marina, a full-service marina offering boat rentals.brThe $250 cleaning fee is not collected with your reservation but is required. You are asked to leave it inside the home upon departure for the housekeeper. To be clear, this $250 is in addition to the other rental costs and taxes that are collected from you upon booking.brbrDuring high seasons, guests must typically check in or out on a Saturday or Sunday, unless stay is more than 14 nights. Exceptions are possible upon request. brbrTRAILER AND VEHICLE PARKING: There is space under home for two standard vehicles. Campers, travel trailers, recreational vehicles, trucks with dual rear wheels and trucks larger than one ton are prohibited from the community. Please park under home and not to the side where it will block your neighbor. I pay for my guests to store their boat or boat on trailer at nearby facilities during their stay. If you will be bringing your boat, or PWC you must tell me now along with your boat description including length. brBoats, PWC and trailers are not permitted to be stored on premises except for day of arrival until noon the next day, and for last 24 hours before departure. Vehicles and trailers may not park on grass or hinder emergency personnel or block any guest’s vehicular access to their home. brbrCONDITION AND USE OF PROPERTY: The Property is provided in “as is” condition. Owner shall use its best efforts to ensure the operation of all amenities in the Property, such as internet access, cable TV access, pool, recreational equipment as applicable. Owner shall not be held responsible for such items failure to work, but will make every effort to correct any issues as reported as quickly as possible. Guest shall use the Property for residential purposes only and in a careful manner to prevent any damage or loss to the Property and keep the Property in clean and sanitary condition at all times. Guests shall refrain from loud noise and shall not disturb, annoy, endanger, or inconvenience neighbors. Guests shall not use the Property for any offensive or unlawful purposes and shall abide by association rules, and not commit waste or nuisance about the Property. brbrExtra fees up to $100 may be charged for excessive cleaning. This fee may apply for failure to follow checkout rules including emptying all trash, damaged or missing items including towels and furniture left out of place.brbrRISK OF LOSS AND INDEMNIFICATION: Guest agrees that all personal property, personal effects and other items brought into the Property by Guest or their permitted guests shall be at the sole risk of Guest with regard to any theft, damage, destruction or other loss and Rental Agent shall not be responsible or liable for any reason. Guest agrees to indemnify and hold harmless Rental Agent and their agents, owners, successors, employees and contractors from and against any costs, damages, liabilities, claims, legal fees and other actions incurred by Guest, their permitted guests, or agents, representatives or successors of Guest due to any claims relating to destruction of property or injury to persons or loss of life sustained by Guest or family and visitors of Guest in or about the Property.brbrRELEASE: Guest acknowledges that use of amenities may be dangerous, particularly with regard to children, and such use is at the Guest’s own risk. Guest waives and releases any claims against Rental Agent, the Property owner and their successors, assigns, employees or representatives for any injuries or death that may be sustained by Guest or their permitted guests or invitees on or near or adjacent to the Property, including any common facilities, activities or amenities including but not limited to pools, decks, kayaks, paddleboards, bicycles, snorkeling equipment and floats. Guest agrees to use any such facilities or amenities entirely at the Guest’s own risk and responsibility. brbrREFUNDS: If evacuation, or delayed arrival, due to a named storm is necessary, the unused portion of Guest payments will be refunded.brbrSMOKING AND PET POLICIES: Home is pet free and non-smoking both inside the home and on balconies. brA minimum fee of $250 will be charged for violation of either policy.brbrSUNRISE BEACH COMMON AREA RULES:br1. Use of common area including pool, beach, dock and TIKI hutbra. Limit noise to conversation level after 10PM brb. No loud music or boisterous noise at any timebrc. No glass containers permitted brd. Children must be supervised at all timesbre. No running, rough play or divingbrf. Animals are not allowed in the poolbrg. No smoking unless downwind from other guests and homesbr2. Trash and Recycling:bra. All trash should be disposed of from homes and common areas in closed 13-gallon bags and placed inside the dumpster. brb. All recycled goods (cans, bottles, cardboard) should be placed loose inside the blue recycle cans WITHOUT bagging. br3. Use of marina and boat docksbra. Drive on docks and all mooring positions are on a first come first serve basis. There is no reserving of dock space. Drive on docks for boats 17 feet and smaller.brb. One motorized watercraft up to 25 feet in length is permitted per home with beam under 9 feet. Exceptions can be made for additional personal water craft based on available space.brc. Please be mindful of depth and stay inside of marker buoys.brd. Fish cleaning station is provided. Please hose any fish remains into bay and do not place into trash.br4. There are no common area spaces for parking. brContact for Questions or Issues: See home info inside unit.

Oceanside home, dock,kayaks,bikes,pool,fishing,109

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$362.02

Summary:brbrBeautiful 3 bedroom, 2 bathroom canalfront home on Cudjoe KeybrbrbrbrThe Space:brbrWelcome to your perfect waterfront retreat on Cudjoe Key! This like-new 3 bedroom/2 bathroom monthly rental is situated on a boating canal with a short run to open water, offering you a slice of paradise with endless opportunities for relaxation and adventure.brbrbrbrAs you step into the spacious living area, you'll immediately feel at home with a huge leather reclining sectional. The well-stocked kitchen and dining area, with seating for 4 at the table and 4 at the breakfast bar, make mealtime a breeze.brbrbrbrThe three large bedrooms provide comfort and privacy in the following setup:brbrbrbr- King bed in the primary, with en-suite bath with soaking tub, separate shower and walk-in closet.brbrbrbr- Queen bed in the 2nd bedroom (shared full bath off hallway)brbrbrbr- 2 twin beds in the 3rd bedroom (shared full bath off hallway)brbrbrbrStep outside onto the covered porch to soak in the tropical atmosphere. Stay connected with high-speed Internet and WiFi. Bring your own streaming services or enjoy the offerings on the flat-screen smart TVs in the living area and each bedroom.brbrbrbrA ride down the canal from the concrete dock takes you to Cudjoe Bay and a 20-minute run to the reef, or take a short journey through Bow or Kemp channels, which open up the backcountry for your exploration. Cook your catch on the gas grill and dine al fresco in the shade. The boat lift (not pictured) and downstairs storage are for owner use only. There's room for a 25-foot boat at the dock.brbrbrbrWhether you're an angler or just looking for a serene waterfront escape, this monthly rental on Cudjoe Key is your gateway to the ultimate Florida Keys experience. Book now and create lasting memories in this waterfront paradise!brbrbrbrCudjoe Key is a laid-back island just 22 miles away from the excitement of downtown Key West. Some of the best restaurants in the Lower Keys are found here, including the famous Square Grouper and island steakhouse Broil. There are public and private boat ramps nearby. A large grocery store is just a few miles away.brbrbrbrPlease note: The primary guest must sign a rental agreement regardless of booking platform. This home requires a minimum 28-day stay per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. Overnight occupancy is limited to a maximum of 6 people, and all guests need to be registered with the property manager. No smoking. One small dog permitted with $250 pet fee and manager approval. There's a cap on electric ($250) and water/sewer ($150).

Sailfish Retreat | Cudjoe Key canalfront getaway

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$328.13

Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities include central air conditioning, new tile floor, new furnishing and decorations throughout, wireless internet, flat screen television, washer, dryer, dishwasher, microwave and covered porch. Master bedroom has a queen bed with lots of closet storage, flat screen television and private full bathroom. Guest bedroom has a queen bed with full length closet storage, private full bathroom entrance. Living room features a queen sleeper sofa with flat screen television and access to covered porch. Beautiful open water views and quick access to the ocean or gulf from this property. 7 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.brbrPlease e-mail with any questionsbrbrRental agreement is agreed upon once you book 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

Island Therapy

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$415.25

CASA KEY LIME - VO291 BRING YOUR BOATbr35' Dockage Open Water Views!brStilt 2Bd/2Ba, Free WiFi! Walk to Pool!Beautiful 2Bd/2Ba stilt vacation home features fabulous open water views only 4 lots in from open water for great tropical breezes and spectacular turquoise blue waters! Great for the avid boater, with 35' concrete protected dockage equipped with dock posts, cleats and swim ladder. Living room offers double slider doors that lead to the covered porch and offers additional sleeping with sleeper sofa. Master bedroom features a queen bed with flat screen television and private full bathroom. Guest bedroom features a queen size bed with access to the balcony and flat screen television. Additional amenities include central air conditioning, full size washer and dryer, dishwasher, free WiFi, 3 flat screen televisions, ceiling fans, patio furniture and covered parking. SECURITY DEPOSIT REQUIRED, NO SMOKING, NO PETS,br7 DAY MINIMUM LOBSTER SEASON, WIFI IN REC HALL, OVERFLOWbrPARKING ADDITIONAL FEE 14 DAYS MAX,brVO REGISTRATION FEE $125 DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY.

Casa Key Lime VO291 Bring your boat

Cudjoe Key, Florida, United States

Bed

Bath

6

Sleeps

$563.66

Welcome to Coconut Telegraph #221 a beautiful 2 bedroom, 2 bathroom waterfront home located inside the private gated community of Venture Out on Cudjoe Key. This inviting retreat is ideal for couples, boaters, and anglers looking to enjoy the Florida Keys with direct water access, resort style amenities, and effortless island living.brThe SpacebrThis elevated coastal retreat offers an open-concept layout and is perfectly positioned along the open ocean, showcasing sweeping water views and endless horizons right from your doorstep. Enjoy front-row sunrises, refreshing sea breezes, and the peaceful rhythm of the Atlantic just beyond your deck.brThe bright and airy living space is designed for comfort after a full day on the water. The dining room table has seating for 5, plus 2 extra seats at the breakfast bar. There is a Black and Decker drip coffee maker as well as a Keurig to enjoy your favorite morning brew. The living room features a 75'' Samsung smart TV and comfortable seating, creating a relaxing place to unwind.brThe home is cooled by central air conditioning and offers high speed Wi-Fi throughout. A washer and dryer are also provided, making longer stays and boating trips easy and convenient.brBedrooms & Sleeping Arrangements:brPrimary Bedroom: King size bed with a 32'' Vizio smart TVbrGuest Bedroom King size bed that can be converted into two twins with a 32'' Vizio smart TVbrMaximum occupancy: 4 guestsbrBathrooms:brThe home features two full bathrooms. brPrimary Bathroom: Walk-in showerbrGuest Bathroom: Walk-in showerbrWaterfront Living, Boating & FishingbrCoconut Telegraph #221 is a dream escape for boaters and anglers alike, set directly on the open ocean and featuring a 35-foot concrete dock that comfortably accommodates boats up to approximately 32 feet. Enjoy effortless access to open water right from your backyard, with unbeatable views to match.brJust a short boat ride away is Looe Key, one of the most famous reef systems in the Florida Keys, offering world class snorkeling, diving, and vibrant marine life in crystal clear waters. Picnic Island is a nearby local sandbar favorite, perfect for relaxing after a morning of fishing.brEnjoy quick access to both:brThe Atlantic Ocean for offshore and reef fishingbrThe Gulf backcountry for exceptional flats and inshore fishingbrAfter a full day in the sun, fire up the NexGrill propane grill and prepare your fresh catch or an easy island-style dinner, then relax and enjoy your meal at the outdoor picnic table while taking in the coastal breeze.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 KnowbrStarter supplies provided: A starter supply of toilet paper and paper towels is provided and typically lasts 1 to 2 daysbrThis home is pet friendly for 2 dogs with a $250 non refundable pet fee per dog.brGolf cart rentals available: $50 per day, subject to availabilitybrVenture Out registration fee: $125 subject to change, paid directly to the community upon arrival. Processing fees may applybrParking: 1 vehicle per unit. Driveway size: 9.5'W x 25'L x 9.9'H. Overflow parking may be available for an additional feebrCommunity 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 after signing your rental agreement with a photo of your ID.brA 4 % credit card processing fee applies to credit card payments.brbrWhether you're watching the sunrise over the Atlantic, heading out for a day of fishing or diving, or simply unwinding on the deck with the ocean breeze and a cold drink in hand, Coconut Telegraph #221 captures the essence of true Florida Keys living. Book your stay today and experience oceanfront living at its finest.

Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$376.29

brbr Located in a great neighborhood at 1032 Spanish Main, this home is perfect for your next vacation. We are at the end of a dead end street so it is very private. This very clean and neat 3 bedroom 2 bath home has a new granite kitchen that has just been enlarged, bar top with 3 bar stools, a table for seating as well, dishwasher, large refrigerator, microwave, Kuerig coffee maker and a regular one, garbage disposal, all the kitchen amenities you can want. The living room is huge with a wrap around leather couch, the large screen TV is on the wall, every bedroom has tvs and fans, the bathrooms are new as well, both with walk in showers and plenty of water pressure. The floors are beautiful large wood tile planks, the full size washer dryer are tucked away in its own laundry room. The living room opens out to a large covered deck overlooking the ocean and canal with comfy large chairs and lights that dim. For your outdoor enjoyment we have a large covered deck overlooking the canal, a large brick patio with a downstairs living room surrounding the pool courtyard, plenty of seating around the pool, refrigerator downstairs with gas grill and sink, large granite bar top, lights that dim for night ambiance, fish cleaning station, hoses for boat cleaning, outdoor shower, we just finished the downstairs bathroom and private storage for you, all is surrounded by very nice landscaping and heated and chilled pool just to name the top highlights! br With a 3.5 foot controlling depth you have open water within 100 feet to get to the ocean or bay fast for fishing, to your favorite spots for diving, snorkeling or lobstering. br At Mile Marker 23, you are close to Key West for all the shopping and entertainment you can handle and more! Oh don't forget about the best place to dine in the keys, THE SQUARE GROUPER, is just down the street!br We have a new aeration system to keep our canal clean and free of sea grass. The canal is full of fish and other sea life, sometimes we have the occasional manatee.br There are games, we have Netflix on the living room and master bedroom tvs as well.br We love our home and want to share it with you.

Waterfront, Heated-chilled pool, Outdoor kitchen, downstairs bathroom w/ shower!

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$303.75

Two bedroom 1 bathroom house .brNew on market, new furniture, new appliances, new painting. brHave a breakfast with view on Atlantic ocean!brMaster bedroom has queen bed, huge walking closet with lots of shelves, room to put away your luggage. Also storige for sleeper sofa bed sheets, blankets and extra pillows. Kids will enjoy bunk beds with best view in the house walking through the room you will get to nice quiet sitting area outside. brLiving room has two sofas only one of them is pull out with queen mattress. brBathroom has walking shower and entire bathroom is pretty spacious with plenty towels.brNew washer and dryer with additional storage above with beach towels. brKitchen is spacious with full size stove , microwave and dishwasher side by size stainless steel refrigerator with icemaker. Kitchen is fully stock for your comfort.brIn front of the house is an other comfort sitting area with gas grill. brAfter all this house is in very popular gated community Venture out, with 2 heated pools, jacuzzi, playground, tennis and basketball courts. Community center offers pool tables, darts, books and lots of board games.brTwo boat ramps are available with pressure washing machine when u clean off your boat or trailer.brCommunity store offers little bit of everything you need due your stay.brOnly one car can be park by the house, other one as well as a boat trailer is subject to extra charge $5 per night collected by association. brWhen arriving you will need to register in office and pay $125 one time fee per your stay( not per person!) collected by association for all amenities.

Lower Keys paradise

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$393.75

Canal Front 35 Seawall - Simply elegant describes this 2 Bedroom with 2 full Bathrooms, canal front stilt home! This home features a 35 concrete seawall with access to the Gulf & Ocean! Ocean views from the dock and porch! Dock amenities include dock posts, cleats and fish cleaning table. Covered porch with comfortable lounging furniture overlooking the water. Interior features tile flooring, mounted living room flat screen TV, full line of appliances, washer, dryer, ceiling fans and central A/C. Sleeping accommodations include a Queen size bed in the Master bedroom and a private bathroom, a Queen bed in the Guest bedroom. Additional sleeping accommodations include a sleeper sofa in the living room. Downstairs features access to a secure storage room, 2 bikes, bait freezer and covered parking. Additional amenities include in-home free WIFI, basic cable, and gas grill. br***Please Note: Venture Out Charges a Registration Fee of $125.00, this is paid at the time of your arrival, at check in. br** ONLY 40 PARKING SPACES AVAILBLE FOR OVERFLOW - EXTRA PARKING SPOTS ARE *NOT* GUARANTEED BY VENTURE OUT AND ARE FIRST COME FIRST SERVEbrVENTURE OUT IS ONLY ALLOWING 1 additional vehicle OR boat trailer per homebrIf you need Overflow Parking when you arrive: $5.00 under 20 ft. or $10.00 for 20 ft. or over per nightbrbrAdditional Parking/Storage Lots:brPlease take note, some of these businesses are closed on Saturdays and Sundaysbr1. B&B Storage: 850-890-3331 - Corner of US1 & Spanish Main Drbr2. Spindrift: 305-745-3131 - 22885 Cutthroat Dr. Cudjoe Key, FL 33042br3. Cudjoe Boat Rentals & Repairs: 305-745-2352 - 447 Drost Dr. Cudjoe Key, FL 33042br4. Big Pine Sea Center: 305-741-7223 - 29740 Overseas Hwy Big Pine Key FL 33043br5. Big Pine Industrial Park: 305-872-4457 - 100 Industrial Park Big Pine Key 33043br6. Big Pine Storage: 305-872-2590 - 30677 Overseas Hwy Big Pine Key 33043

VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$554.57

Beautiful Waterfront Home with Stunning Ocean Views!brWelcome to this amazing Florida Keys getaway at at Caribbean Blue #517! This beautiful 2-bedroom, 2-bath home offers everything you need for a relaxing and enjoyable Florida Keys vacation. Situated on a beautiful Oceanfront lot, you'll be captivated by breathtaking ocean views from your private back patio as well as the downstairs patio where you can unwind and soak in the scenery. Whether 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.brKey Features:br*Spacious Bedrooms: Two cozy bedrooms designed for comfort, ensuring restful nights after your adventures.brThere is a King size bed in the primary bedroom and two twin beds that can be combined to make an additional king size bed.br*Two full Bathrooms, one is located in the primary bedroom, both have standup showers.br*Open Kitchen & Dining: The fully equipped kitchen opens to a vibrantly appointed dining area with lots of beautiful Lily Pulitzer decor that comfortably seats up to 4 with an additional 2 guests at the kitchen island, perfect for family meals or entertaining friends. There is a Cuisinart dual drip and pod coffee maker at this home for you to enjoy your favorite brew.br*Outdoor Oasis: Enjoy the expansive 32' wrap-around concrete seawall that can accommodate up to a 29' boat. Plenty of room for fishing, sunbathing, or simply enjoying the gentle ocean breeze.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*Laundry Facilities: A washer and dryer are available within the home, so you can pack light and keep your clothes fresh throughout your stay.brThis property #517 rents out quickly, if it isn't available you may want to check out its sister property Unit 319.brNo Pets allowed at this home.brA 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.brVenture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your stay to the next level. Indulge in resort-style amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts.brAdventure beyond the gates for a bite to eat at some of Florida Key s favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki s Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away!brWhether you re a seasoned angler eager to explore the abundant fishing grounds or simply seeking relaxation by the water s 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 25'L x 9'W x 12H'. 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!

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Cudjoe Key, Florida, United States

Bed

Bath

Sleeps

$846.18