Vacation Rentals By Owner In Summerland Key, FL

Breathtaking sunset views! Fully stocked kitchen with all appliances you need for at home cooking. Spacious rooms with dreamy tempur-pedic beds and big California style closets. Waterfront Pool with private beach access. Dock up to a 29 ft boat. Walking distance to the “Square Grouper” restaurant. Near by Market, boat and water sports rentals. 30 min drive from Key West. You wont want to leave!

Waterfront House in the heart of Cudjoe Key.

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$225.78

Our Cudjoe key home is only 23 miles from Key West. The swimmable canal has direct access to Cudjoe bay which is only 200 yards away. You can boat into the Atlantic or Gulf of Mexico within minutes. Our home has a new kitchen (fully stocked for large families), new floors, and a large outdoor patio upstairs. Our home also includes a walk around deck. Downstairs there is a chest freezer, commercial ice machine, bait freezer and extra fridge. Two hole putting green next to dock (putters and balls included). Two (2 person kayaks) and 3 bikes. After a day of boating/swimming rinse off in our outdoor shower with hot and cold water. Great restaurants are just minutes away or drive a few miles into Key West. The location is absolutely perfect.

Special Rate Available September 2026 book now

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$240.19

Summary:brbrDog-friendly canalfront boating home on Cudjoe KeybrbrbrbrThe Space:brbrAll the comforts of home, with none of the cold weather! Dog-friendly 2 bed/2 bath monthly vacation rental on a boating canal on Cudjoe Key!brbrbrbrOpen main living area with large dining table, small bar and plenty of seating. Roomy kitchen features a breakfast bar with room for four, tile counters, stainless steel appliances and a pantry. Master bedroom has king bed, TV, walk-in closet and en-suite bath. Second bedroom has queen bed, TV and easy access to main bath. WiFi and Apple TV. Room for your boat along the concrete seawall. Please note: The owner's boat will be parked in the yard during your stay. Covered outdoor seating and dining downstairs. Plenty of parking. For anglers and snorkelers or divers, it's a 5-minute ride down the canal to Cudjoe Bay, a 20-minute run out to the reef and a short run through Bow or Kemp channels to the backcountry.brbrbrbrThis 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 5 people, and all guests need to be registered with the property manager. No smoking. Up to 2 dogs permitted with manager approval and nonrefundable pet fee of $250 per pet. Absolutely no cats due to allergies. There's a cap on electric ($300) and water/sewer ($150).brbrbrbrGuest Access:brbrGuests have the house to themselves.brbrbrbrThe Neighborhood:brbrCutthroat Harbor Estates, a residential neighborhood of mostly single-family homes, is on the ocean side of Cudjoe Key, an island 23 miles from Key West. The famous Square Grouper restaurant is nearby. There is a convenience store and two seafood markets on the island. The closest boat ramp is Cudjoe Marina in the Cudjoe Gardens neighborhood nearby.brbrbrbrGetting Around:brbrA car is recommended. There is a city bus that runs from Key West to Marathon several times a day. The Lower Keys have limited taxi service and Uber/Lyft.brbrbrbrInteraction with Guests:brbrContact-free checkin and checkout are available. We value our guests’ privacy but are always available if needed.

Sunshine 23 | Dog-friendly canalfront home

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$349.13

This is an oceanfront vacation rental in the world-famous Florida Keys on secluded southern end of Summerland Key, mile marker 25; if you know, you know it freatures location, location, location! brbrThe house is an open floor plan with panoramic Atlantic Ocean views and a large wrap-around deck. It includes the best of both worlds: an oceanfront private sand beach and protected canal dockage with instant access to open water. Enjoy sunrises, the glow of the southern sky at sunset, and the night sky. When was the last time you saw the Milkyway brbrThe Key-ver beach house offers you a home base for fishing, diving, and adventures by sea, quick trips to Key West for tours, shopping, or happy hour and a quiet place to kick back and enjoy island life with a spectacular view. brbrIncluded with the house are:br-Protected canal dockage for one private vessel up to 36'br we will consider 2 boats (size for dockage will be considered)br-Private oceanfront sand beachbr-Hot tub with/ocean view in the shade under upperlevel deckbr-High-speed wifibr-bate fridgebr-ice makerbr-outside showerbr-Kayaks (2)br-Bicycles (2)br- & much more! brbrThe south end of Summerland Key is quiet and exclusive. No long canal rides to figure out the wind and conditions, look out the window and choose when to go, 600' ride to Niles Channel then easy access to the gulf side or ocean side. brbrAlso, see amenity details.brbrAbout the Living Space: The house is a 2 bedroom/2 bathroom elevated living space with an open floor plan. Off the main living area are two bedrooms: the ocean view bedroom with a king-size bed, and the palm room has a queen bed, with a canal view and south side window ocean view; the palm room also has its own bathroom. The sunroom offers a panaramic ocean view with a day bed that folds out to a queen size bed as well. Central air, ceiling fans, and tile floors throughout the upper level living area. Enjoy the large upper-level open air deck under which sits an infinity view hot tub and area for shade seekers. A laundry room in which outdoor gear may be stored is located on the lower level, as is a bate fridge and icemachine. There is also a secluded outside shower (with an ocean view) for your enjoyment.brbrPlease check available months on the calender.

Fishermens' dream B.Y.O. boat ocean front with protected canal 600' to bluewater

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$235.92

Enjoy the view from the large porch overlooking a deep, wide, crystal blue, clear canal with quick boating access to both the Atlantic Ocean and Gulf of Mexico. Looe Key Coral Reef is a short distance away by boat for some of the best diving & fishing the keys has to offer. If you prefer to stay home, enjoy the canal loaded with marine life, and catch fish from our 60 ft. concrete dock where you can anchor your boat. The lovely 3 Bedroom 3 Bath Summerland Key home features an open floor plan with brand new 2023 quartz kitchen countertops & backsplash and dining room set. Centrally located between Key West and Marathon at Mile Marker 24. Large permitted bonus area downstairs. *Living room furniture backs up to an open staircase, not suitable for young children. Separate addendum will follow and be made part of lease agreement.*Tenant will be given an allowance of $500 total for electric and water & sewer. Anything above $500 will be the tenants responsibility.br

LIVING IN BEAUTIFUL PARADISE

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$327.0

Consider this house your home away from home while you visit Sugarloaf Key. This beautiful property is a 2 story canal front home perfect for a family or group of friends. Guests can unwind in style. Kickback, relax, and enjoy everything Sugarloaf Key and our house has to offer.brbrThe home is an open concept, includes 3 bedrooms and 3 full bathrooms with 2 large outdoor porches overlooking the canal and over the trees to the ocean. The home is fully equipped with everything you need including televisions, games, linens, kitchen appliances and extras.brThe first floor includes the open concept modern kitchen with quartzite counters and large island with six seats, dining room, living room with reclining sectional, full bathroom with walk in in shower, guest bedroom, and laundry room. In addition to a large outdoor balcony with patio set and grill. brThe second floor includes a guest bedroom and guest bath. In addition to the master suite which is fully equipped with a king size bed, flat screen tv, walk in closet, spacious private bathroom including a double vanity, walk in shower, jetted tub, mini bar, and a private balcony overlooking the canal. brbrThe backyard has an 80 x 10 ft dock with boat cleats and ladder into the canal. The canal can accommodate up to a 28 ft boat.brbrEnjoy the ground floor with a converstaion patio set, television, yard games, bicycles, canal fishing, and paddle boards.brbrThe home has parking for at least 4 vehicles and a trailer. brbrInquire for multi-month discounted rates for extended stays. brbrbr

Canal Front 3-bedroom house in Sugarloaf Key

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$336.14

Private 3 bdrm, 2 bath, home in exclusive Cudjoe Gardens @ MM20 on Cudjoe Key. This is a very comfortable home in a nice neighbourhood. If you are looking to rent a beautiful home in one of the most prestigious neighborhoods, (Cudjoe Gardens) you won't be disappointed. Great area to ride bikes and go for walks. Property backs onto deep water canal with easy access to Back Country and Atlantic Ocean for excellent fishing. Canal is clean and suitable for swimming with ladder. We just installed a Pool and renovated our Kitchen. Minimum 28 day rental required.brLarge screened in lanai, with love seat, 2 chairs and dining set. Fully outfitted kitchen with fridge, stove, ice maker, microwave, dishwasher and more. Laundry Facilities. New fridge in the garage for beer and bait Large flat screen TV with full cable, unlimited highspeed internet and wifi. brLarge Master Bedroom with en-suite bathroom. 2nd bedroom with new queen bed . 3rd bedroom, queen, is private off the lanai.brThere are 4 bikes and a canoe for your use.br20 min to Key West, located @ MM20 . Property is in an excellent location. This is a beautiful vacation property. The whole house has been renovated and is like brand new. The deep water canal is clean and you can swim in it. If you are into fishing you can dock your boat (max size allowed is 24 ft) and have easy access to the best fishing in the keys. Cudjoe Marina is down the street and easily accessible by boat for bait and fuel. There is a large supermarket on Big Pine Key, 10 minutes away.brClose to looe key dive shop. Fresh fish market around the corner and Mangrove Mamas is within walking distance. brFlying into Key West and renting a car is a breeze. Downtown Key West is only a 20 minute drive.

Cudjoe Key 3bdr,2 bath Pool, 20 min from Key West, Ocean Access, Bikes, Canoe

Summerland Key, Florida, United States

Bed

Bath

6

Sleeps

$787.5

The Roost in Summerland Cove Isles affectionately know as 'The Castle' is truly a gem nestled in a highly desirable neighborhood with excellent deep-water access to the Gulf Atlantic near some of the best fishing spots in the Florida Keys. This concrete constructed retreat offers not only roof top Ocean views, but also meticulous attention to detail, quality workmanship and an array of desirable amenities including RV parking with 50 AMP electric service, a heated pool and spa, and a concrete rooftop deck with water and electric service that provides 360-degree panoramic views of the surrounding landscape offering the perfect vantage point from which to watch the Sun rise and set over the glistening Ocean. Inside, the home boasts 4 bedrooms and 3 baths, including a permitted guest quarters with its own entrance and screened patio. The open concept kitchen and living area seamlessly flow into the expansive screened patio, creating an ideal space for entertaining while enjoying the picturesque outdoor views. Each bedroom has its own private entrance and the master suite, occupying the entire third level, is a true retreat with an open bonus room and private veranda. The rooftop balcony is the best view from the neighborhood for sunrise and sunsets. 550 pound commercial icemaker deep freezer and extra fridge in garage .10,000 lb. davits, an outdoor shower, and a convenient fish cleaning station. hang out in the pool and watch the game or your favorite show on the 100 inch flatscreen .The impressive outdoor space also includes covered patio, tropical landscaping, parking for multiple vehicles, and a built-in SWAT mosquito and no-see-um control system ensuring a comfortable and enjoyable environment year-round. 'The Roost' offers a perfect blend of luxury, comfort, convenience, and outdoor living, making it an ideal retreat for those seeking the ultimate waterfront lifestyle in the Florida Keys.

The Roost in Summerland Cove Isles

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$444.87

Enjoy boating, swimming or just the ocean view in the greatest of privacy. Dinner and entertainment in Key West is a short drive or 7-minute walk to the county bus ride away. Enjoy walking or bicycle riding in a quiet peaceful neighborhood and even walk to lunch or dinner at the nearby local restaurant Square Grouper. 31 ft dock for your boat with water and electric at dock. See our other VRBO properties listing numbers 2784733 and our newest one 3023197 !

Oceanfront Home With Large Private Deck with boat dockage

Summerland Key, Florida, United States

Bed

Bath

6

Sleeps

$671.55

Beach Bliss has everything you need for a spectacular vacation. The views inside and outside the home are mesmerizing. The exterior area of the home features lush tropical landscaping, a sparkling pool overlooking the ocean, and a large boat dock with some of the best boating in this area. You can relax in the pool or go for a swim in the ocean in your own private beach area. There is a large deck overlooking the pool and ocean for morning coffee or evening cocktails. The interior of the home features a large kitchen with the most amazing views. Right off the kitchen is a big open living room with a TV for evenings after fishing where you want to wind down and relax. Two of the bedrooms each have a queen bed. The master bedroom features a large open space with a king bed and a large master bathroom with a separate shower and bathtub. The fisherman, diver, or explorer will never lack things to do. Nearby you will find grocery stores, post office, banks, restaurants, fuel, marinas, and sightseeing. The remarkable beaches at Bahia Honda State Park are a few miles north, while Key West and its unique attractions are a half-hour drive south.This is a non-smoking home. No pets. THIS HOME IS A 28-DAY MINIMUM RENTAL PER MONROE COUNTY CODE. br

Beach Bliss, Oceanfront with pool

Summerland Key, Florida, United States

Bed

Bath

8

Sleeps

$285.74

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to Keys Breeze, a beautifully updated 3-bedroom, 2-bath home on Ramrod Key that perfectly captures the relaxed luxury of the Florida Keys. Thoughtfully refreshed with an updated kitchen and stylishly renovated bathrooms, this home offers a bright, modern coastal feel designed for comfort after long days on the water. brbr brbrBoaters and anglers will appreciate approximately 25 feet of dockage and quick access to both the Atlantic Ocean and the Gulf of Mexico. Spend your mornings fishing offshore in the Atlantic and your afternoons cruising the calm Gulf waters to nearby sandbars. Please note, the boat lift and owner’s boat are not available for guest use. brbr brbrThe heated saltwater pool creates a private outdoor oasis perfect for soaking up the Keys sunshine, cooling off after a day on the water, or relaxing under the stars in the evening. brbr brbrInside, the home is designed for easy, comfortable living with an elevated yet welcoming feel, making it ideal for families, couples, or friends traveling together. One dog up to 60 pounds is welcome, so your four-legged companion can join in on the adventure. brbr brbrConveniently located, Keys Breeze offers a peaceful island setting while still being close to everything. You’re just about 40 minutes from Key West’s dining, nightlife, and attractions, and approximately 25 minutes from Marathon for additional restaurants, shops, and activities. brbr brbrWhether you're here for world-class fishing, boating, or simply unwinding in a beautiful waterfront setting, Keys Breeze delivers the perfect Florida Keys escape. brbr brbrSLEEPS MAXIMUM OF 8 GUESTS: brbr brbrBedroom 1: King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2: Queen Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 3: Full Bed brbr brbrLiving Room: Sectional Sofa w/ Pull-Out Full Bed, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- Saltwater Pool (21'x11', depth 3.5' to 5.5', heated to ~85 degrees Nov-Apr) brbr brbr- 25' of Dockage (Owners boat will be on the boat lift and boat and lift are not for guest use) brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Drip Coffee Maker, Keurig, Toaster, Blender brbr brbr- Parking for a maximum of 4 vehicles (including boat trailers) on the property. RVs may not be parked on the property. brbr brbr- Linen's and towels provided 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 brbrNo Smoking: Smoking is strictly prohibited within the property. For the comfort and safety of all guests, please refrain from smoking indoors. brbr brbrPet Policy: Up to one friendly and well-behaved dog 60 LBS or less 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 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 door and driveway. These cameras are for security purposes only and do not monitor any private interior or exterior s

Keys Breeze: 3BR Ramrod Retreat w/ Pool, Dockage, Atlantic & Gulf Access, Parking & Dog-Friendly

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$193.53

Amazing canal front 3 bed conch style house located in prestigious community of Summerland Key Cove. It is the first canal from open water and one of just a few flow-through canals providing excellent water quality. The canal is deep and wide. Expect to see lobsters, crabs and other sea life on the sea wall. You will be surrounded by million dollar homes and just a few minutes boat ride from open water in the Gulf and Atlantic.brProperty is close enough to Key West to matter (20 miles) but far enough away for R&R (rest and relaxation). Being on the end of the Key, prevents the irritating noise of Hwy 1 traffic, which is rare to find. brFeatures include:brSeawall with step down to waterbrHandicap accessiblebrLarge downstairs storage brGreat access to gulf and Atlantic. brRV & Motor Coach Storage/Parking AllowedbrLarge yard brHigh speed internetbrSmart TVbrLarge outdoor porch of main living areabrTile flooring throughout homebr42 Flat Screen TV in Living RoombrSwim canalbrLadder on seawall to get in and out of swim canalbrFull size washer & dryerbrDeep/wide/flow-through canal brFishing & scuba paradisebrGrillbrCocktail Table On Canal SidebrFish cleaning tablebrBait freezerbrbrL17000140687

Ground Level Home With Deepwater Canal

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$473.19

Get ready to relax in this beautiful 3-bedroom house in Summerland Key Cove. This property features three large bedrooms perfect for a family or friends. With 4 bathrooms everyone will have their own space to freshen up. Enjoy amenities like 70 feet of seawall of a deep-water canal. Canoeing, paddle boards, bike riding and of course fishing. FIVE minutes to ocean. There are so many nearby sandbars and snorkeling reefs. The hammock and pool is perfect for the days you just want to relax.

Sea Glass House of Summerland Key! Pool, 70 feet of Seawall, deep water canal!

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$481.97

This Summerland Key house has 3 fully furnish bedrooms, including a king bed, a queen bed, and a Murphy bed. Guests enjoy 2 bathrooms, making it easy to relax and refresh. The space stays comfortable year-round with air conditioning and heating. A boat lift for a max 25ft boat is also available for your convenience. Bright ambiance and beach smells At your welcome entrance it also offers a nice blend of comfort and practicality. We think our place will help you experience everything Summerland Key has to offer.

Warm and relax 3-bed 2 bath home in charming Summerland Key minutes from K.West

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$107.38

Our private studio is located on beautiful Cudjoe Key. It has a private entrance with no accessibility to the main house. We are located at 22.5 mm from Key West. It’s a great room to stay in while visiting the Florida Keys. The space is great for single travelers. brbrGreat studio apartment with kitchenette that has a full size refrigerator, coffee maker, Nuwave oven, microwave, and hot eye for cooking. TV is located in the main living area. There is 1 Queen bed. There is a full bath inside with shower and outside shower. There are also 2 chairs for relaxing in to watch tv. It is approximately 400 sq ft. brbrThere is a bar for 2 and an outside table with seating for 4, swing and a couple of other chairs around the property for your use. There is parking for one vehicle.brbrFree WIFIbrbrThere are 2 paddle boards and 2 kayaks for your use during your stay. brbrWe live here full time and have 2 dogs.brbrIt is a very quiet neighborhood and close to Big Pine for getting groceries or essentials. We are about 10 miles from Bahia Honda State Park and about 20 miles from Smathers Beach and the Southern Most Point in Key West.

Apartment

Lower Keys Escape

Summerland Key, Florida, United States

1

Bath

Sleeps

Exceptional(1)

$353.36

Summary:brbrGorgeous canalfront pool home close to open water on Cudjoe KeybrbrbrbrThe Space:brbrEscape to a slice of paradise on Cudjoe Key, where luxury meets tranquility in this stunning 3-bedroom, 2-bathroom stilted home with pool on a boating canal. This monthly rental offers a perfect blend of upscale comfort and coastal charm, providing an idyllic retreat for your Key West getaway.brbrbrbrStep inside to discover a beautifully appointed interior, where every detail exudes warmth and sophistication. The spacious living area invites you to unwind with plush furnishings and stylish accents, while large windows bathe the space in natural light and offer enchanting views of the surrounding waterfront paradise.brbrbrbrPrepare delicious meals in the gourmet kitchen, equipped with modern appliances, sleek countertops, and ample cabinet space. Adjacent to the kitchen, the dining area sets the stage for memorable gatherings with loved ones, while sliding glass doors seamlessly connect the indoor and outdoor living spaces.brbrbrbrVenture outside to experience the ultimate in outdoor living, where a waterfront pool beckons you to soak up the Florida sunshine and cool off with a refreshing swim. Lounge on the expansive pool deck, furnished with comfortable seating and dining areas, as you savor the gentle sea breeze.brbrbrbrFor a truly unforgettable experience, ascend to the rooftop deck and witness the spectacle of the sun rising and setting over the horizon, casting a mesmerizing palette of colors across the sky.brbrbrbrBoating enthusiasts will delight in the convenience of the 40 feet of dock space, just steps from your door. Launch your own vessel or explore the surrounding waters by kayak or paddleboard, immersing yourself in the natural beauty and serenity of the Florida Keys.brbrbrbrWhether you're seeking adventure on the water or simply seeking solace amidst the beauty of the outdoors, this exquisite vacation rental offers the perfect blend of luxury, comfort, and coastal living for your Florida Keys escape. Indulge in the ultimate vacation experience at this stunning waterfront oasis on Cudjoe Key.brbrbrbrPlease note that during your stay, the owner's boat will be stored on the lift and his vehicle will be parked under the house, but there's still plenty of room for you to park your vehicles and trailer.brbrbrbrThe primary guest must sign a rental agreement. 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. Small dog permitted with manager approval and nonrefundable fee. There's a cap on electric ($300) and water/sewer ($150). Pool heat is an additional $15 per day.brbrbrbrGuest Access:brbrGuests have the house to themselves.brbrbrbrThe Neighborhood:brbrCutthroat Harbor Estates, a residential neighborhood of mostly single-family homes, is on the ocean side of Cudjoe Key, an island 23 miles from Key West. The famous Square Grouper restaurant is nearby. There`s also a convenience store and two seafood markets on the island. The closest boat ramp is at Cudjoe Marina in the Cudjoe Gardens neighborhood nearby.brbrbrbrGetting Around:brbrA car is recommended.brbrbrbrOther Things to Note:brbrA car is recommended. There is a city bus that runs from Key West to Marathon several times a day. The Lower Keys have limited taxi service and Uber/Lyft.brbrbrbrInteraction with Guests:brbrContact-free checkin and checkout are available. We value our guests’ privacy but are always available if needed.

Foster's Folly | Gorgeous canalfront pool home

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$283.3

Summary:brbrOceanside monthly rental in the Lower Florida Keys with 60 feet of concrete dockage, bait freezer, fish-cleaning station, and quick open-water access — ideal for anglers, boaters, and extended Keys stays.brbrbrbrThe Space:brbrWelcome to Bahama Breeze in the Keys, a relaxed oceanside retreat designed for extended stays in the heart of Cudjoe Key. Tucked into a quiet residential neighborhood, this waterfront home blends island comfort with excellent boating access and easygoing coastal living.brbrbrbrInside, the open and airy layout features warm pine floors, vaulted ceilings, and two distinct living areas — perfect for spreading out, entertaining, or unwinding after a day on the water. The updated kitchen is equipped with stainless-steel appliances and quartz countertops, making everything from casual breakfasts to sunset dinners effortless.brbrbrbrThe main level offers two king bedrooms, comfortably furnished for restful nights, along with a shared full bathroom. A spiral staircase leads to a cozy open loft with a full-size bed, ideal for additional guests. The great room also includes a comfortable fold-out sofa, plus a convenient half bath off the living area.brbrbrbrOutdoor living is where Bahama Breeze in the Keys truly shines. A wrap-around covered porch, accessible from every room, invites you to enjoy cooling sea breezes throughout the winter months.brbrbrbrBoaters and anglers will appreciate:brbr- 60 feet of concrete dockagebrbr- Swim ladderbrbr- Fish-cleaning stationbrbr- Bait freezer and ice makerbrbr- Lots of outdoor seatingbrbr- Outdoor shower with hot and cold waterbrbr- Gas grillbrbr- Fully fenced yardbrbrbrbrWhether you’re heading out at sunrise or winding down dockside in the evening, everything is in place for effortless Keys living.brbrbrbrComforts & Amenities:brbr- High-speed internetbrbr- Smart TVs in the living room, both bedrooms and the loftbrbr- Lockable storage shed for personal items or outdoor gearbrbr- Contact-free check-in and check-outbrbrbrbrImportant Notes & Rental Details:brbr- Minimum 28-day stay required by Monroe County ordinancebrbr- Primary guest must sign a rental agreement, regardless of booking platformbrbr- Proper county and state taxes collected, regardless of booking platformbrbr- Primary renter must be 25+ years oldbrbr- Maximum overnight occupancy: 6 guestsbrbr- No smoking on the propertybrbr- One small or medium dog permitted with manager approval and a $250 nonrefundable fee. No cats. brbr- The downstairs storage, davits and kayaks are not available for renter use.brbr- Utilities included with caps on usage of $300 for electric and $150 for waterbrbrbrbrBahama Breeze in the Keys is ideal for guests seeking a true long-term oceanside Keys experience — where boating days, porch evenings and unhurried island living come together effortlessly.brbrbrbrGuest Access:brbrGuests have exclusive use of the entire home.brbrbrbrThe Neighborhood:brbrLocated in Cutthroat Harbor Estates, this oceanside residential neighborhood is known for its laid-back atmosphere and proximity to boating and fishing grounds. The popular Square Grouper Bar & Grill is nearby, along with a convenience store and local seafood markets.brbrThe closest public boat ramp is Cudjoe Marina, just minutes away.brbrKey West is approximately 23 miles west for dining, shopping, and entertainment.brbrbrbrGetting Around:brbrA car is recommended. There is a city bus that runs from Key West to Marathon several times a day. The Lower Keys have ride-share services and limited taxi service.brbrbrbrInteraction with Guests:brbrWe respect our guests’ privacy while remaining available whenever needed. Contact-free check-in and check-out are provided for a seamless arrival and departure.

Bahama Breeze in the Keys

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$520.66

Summary:brbrNewly renovated & expanded, amazing pool, dockage & boating access on Summerland KeybrbrbrbrThe Space:brbrLuxury Waterfront Living on Summerland KeybrbrbrbrEscape to the Florida Keys and indulge in island living at its finest in this spacious 5-bedroom, 3.5-bath pool home on coveted Caribbean Drive East. Designed for both relaxation and adventure, this gated retreat offers direct deep-water boating, open water views and breathtaking sunset hues.brbrbrbrA gorgeous remodel brings modern elegance throughout. The new primary suite is a private sanctuary with a king bed, a spa-inspired en-suite bath featuring a huge walk-in shower, dual vanities, and a soaking tub — plus a private waterfront patio perfect for morning coffee or evening cocktails. Additional guest accommodations include two queen bedrooms on the main level that share an upgraded Jack-and-Jill bathroom, plus thoughtfully designed spaces that balance comfort and style.brbrbrbrGather in the brand-new, top-of-the-line kitchen, enjoy meals in the light-filled dining area with canal views, or relax in the living spaces that open seamlessly to the outdoors. The large screened porch is ideal for al fresco dining, while the open pool deck invites sun-soaked afternoons beside the deep, heated pool. With plenty of dockage, boating enthusiasts will love the easy access to world-class fishing and snorkeling. Ample parking ensures convenience for you and your guests.brbrbrbrHome features:brbrbrbr- Renovated kitchen with new cabinets, appliances and fixturesbrbr- New king primary suite with luxurious ensuitebrbr- 4 queen bedrooms with 2 full bathsbrbr- Canal-view living and dining areasbrbr- Large screened porch and multiple waterfront patiosbrbr- Main-level laundry and half bathbrbr- Pool, heat optional in winterbrbr- 80 feet of deep-water dockage and a kayak/paddle board rampbrbrbrbrRental Information: This home requires a minimum 28-day stay per county ordinance. Proper county and state taxes are collected regardless of booking platform. Primary renter must be 25 years or older. Overnight occupancy is limited to 10 guests, and all guests must be registered with the property manager. No smoking. Well-behaved dogs are considered with manager approval and a $250 nonrefundable fee. Pool heating is available for an additional $500 per month.brbrbrbrDiscover your private slice of paradise on Summerland Key, where luxury, comfort and the Florida Keys lifestyle come together.brbrbrbrGuest Access:brbrGuests have the house to themselves.brbrbrbrGetting Around:brbrA car is recommended. There is a city bus that runs from Key West to Marathon several times a day. The Lower Keys have limited taxi service and Uber/Lyft.brbrbrbrInteraction with Guests:brbrContact-free checkin and checkout are available. We value our guests’ privacy but are always available if needed.

Reel Caribbean Getaway

Summerland Key, Florida, United States

5

Bed

Bath

10

Sleeps

$134.37