Vacation Home Rentals By Owner In Summerland Key, FL

Unique Waterfront Dome Home with Dock and Pool – Little Torch KeybrbrWelcome to your one-of-a-kind Florida Keys escape. This geodesic dome home is unlike anything else you’ll find in the islands. Nestled on the quiet and charming Little Torch Key, this waterfront property combines Keys character with modern comfort, giving you a vacation experience that’s both unique and unforgettable.brbrWhether you’re here to relax by the water, take the boat out fishing, or explore nearby Key West, our dome house is the perfect place to call home.brbr⸻brbrThe Dome ExperiencebrbrThe house itself is part of the adventure. With its rare geodesic dome architecture, the interior feels open, airy, and full of natural light.br • 2 bedrooms and 1.5 bathrooms on the main levelbr • Additional downstairs space with a full bath and laundry area — ideal for extra guests or hobbiesbr • A spacious living area for gathering after a day on the waterbrbrThis isn’t a brand-new luxury build. It’s a true Keys original with charm, personality, and a casual atmosphere you won’t find anywhere else.brbr⸻brbrOutdoor Living – Waterfront ParadisebrbrThe outdoor spaces are what make this property truly shine:br • Private dock for tying up your boat, fishing, or watching the sunsetbr • 7,000 lb boat lift available by arrangementbr • Above-ground pool for cooling off under the Florida sunbr • Patio and outdoor areas for grilling, dining, and relaxingbrbr⸻brbrLocation – Little Torch KeybrbrThe dome is located in the heart of the Lower Keys, offering a peaceful island setting while still being close to all the action.br • 30 minutes from Key West’s world-class dining and nightlifebr • A short drive to Big Pine Key for groceries, restaurants, and shopsbr • Convenient access to both backcountry and open ocean waters for boating and fishingbr • Near Looe Key Reef, one of the best snorkeling and diving spots in the Keysbrbr⸻brbrPerfect Forbr • Families and groups looking for an affordable waterfront rental with plenty of spacebr • Boaters and fishermen who want direct water access and a private dockbr • Couples and friends seeking a quirky, memorable place to staybr • Adventurers who love snorkeling, diving, and exploring the natural beauty of the Keysbrbr⸻brbrAmenitiesbr • 2 bedrooms plus bonus downstairs spacebr • 2.5 bathrooms (1.5 upstairs, 1 full bath downstairs)br • Private dock and boat lift (negotiable)br • Above-ground poolbr • Laundry areabr • Fully equipped kitchenbr • Outdoor living and dining spacesbr • Wi-Fi, A/C, and essentialsbrbr⸻brbrRental Detailsbr • Monthly rent: $5,000br • Longer stays may be eligible for discountsbr • Flexible terms for the right guestsbrbr⸻brbrWhy You’ll Love ItbrbrThis dome house isn’t just a rental — it’s an experience. From the unique architecture to the waterfront setting, you’ll find yourself relaxing into the rhythm of the Keys in no time. Guests spend their days outdoors, soaking in the views, fishing off the dock, snorkeling nearby, or cooling off in the pool.brbrCome ready for adventure, bring your love for the water, and enjoy a stay that you’ll remember long after you’ve gone home.

Unique Waterfront Dome Home with Dock & Pool – Little Torch Key

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$2295.81

Welcome to your tropical paradise on Ramrod Key! This stunning 6,888 square foot home showcases exceptional quality in both construction and finishes, ensuring a luxurious experience from the moment you arrive. With six spacious bedrooms with 6 ensuite bathrooms plus 2 additional half bath, this massive property comfortably accommodates up to 21 guests. The spacious living area features tons of seating arrangements, custom bar, huge dining table with seating up to 14 and another 6 at the eat in counter bar. There is a hotel quality elevator that services each floor. As well as 2 laundry rooms one upstairs and downstairs for your convenience. The expansive master suite features a large bedroom with a private porch, both offering breathtaking views, and endless sunsets. The indulgent master bath complete with a huge soaking tub that invites you to unwind while soaking in the scenery. Step outside to the infinity edge pool, perfect for relaxing under the sun. For boating enthusiasts, the property includes a heavy-duty boat lift on the dock, providing easy access to the Niles Channel and excellent boating opportunities to both the Gulf of Mexico and the Atlantic Ocean. Designed with entertaining in mind, this exquisite retreat is ideal for executive retreats or large gatherings. No detail has been overlooked including, ensuring that your stay will be nothing short of extraordinary. Book your stay today and immerse yourself in luxury, comfort, and stunning natural beauty!

Luxury 6 Bedroom Open Water Estate on Ramrod Key

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$361.45

Beautiful Ocean/Canal Views 21' Dockage br2Bd/2Ba with Double Porches, Large Landscaped Yard!brIsland Breeze is a fabulous location for this 2Bd/2Ba stilt home in the desirable Venture Out Community on Cudjoe Key. Features a 21' Concrete Seawall with breathtaking views of the Atlantic Ocean and located on a 60' wide canal. Situated on an oversized lot with a patio surrounded by tropical gardens creating lots of privacy between neighbors, it's like living on an Island away from it all! Covered parking and 12 x 12 storage room plus two upper decks facing east and west for great orientation and open air breezes. brbrVenture Out charges a registration fee upon entry of $125.00, payable at the gate upon arrival. When you arrive at Venture Out , you will go to the Venture Out Office (or the Guard Gate if it is after hours) to pay the fee and to receive your parking pass. Cash or CC only is accepted for this fee.brOVERFLOW PARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.

Ocean/Canal Views 21ft Dock - Venture Out #357

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$549.29

Experience the Ultimate Florida Keys Escape at Reel Escape — Your Spacious 4-Bedroom Summerland Key RetreatbrbrNestled in the serene beauty of Summerland Key, just a quick 5-minute drive from pristine Florida Keys beaches, Reel Escape offers everything you need for the perfect vacation — whether you crave relaxation, family fun, or thrilling outdoor adventure.brbrLuxurious Comfort and Space for Family & FriendsbrbrThis expansive home comfortably sleeps up to 7 guests with four generously sized bedrooms spread over two floors, designed for privacy and comfort:brbrMain Floor:brbrThree bedrooms — two with queen beds and one with two twin beds, perfect for kids or friends.brbrA full-size, well-appointed bathroom for easy access.brbrA massive screened-in lanai ideal for year-round outdoor dining and evening relaxation, protected from bugs and weather.brbrTop Floor Primary Suite:brbrThe entire upstairs level is dedicated to the primary suite, offering ultimate privacy.brbrA luxurious king-size bed with high-quality linens.brbrA spacious walk-in closet to store your vacation wardrobe.brbrPrivate patio access with tranquil views — perfect for morning coffee or sunset unwinding.brbrEn suite full bathroom featuring modern fixtures and plenty of space.brbrChef’s Dream Kitchen & Dining ExperiencebrbrCalling all food lovers! The kitchen is fully stocked and thoughtfully equipped to inspire your culinary creativity:brbrModern appliances including stove, oven, refrigerator, and microwave.brbrSpecialty items like a lobster pot and grill for fresh seafood feasts.brbrBlender, coffee maker, toaster, and dishwasher to make your stay effortless.brbrAmple counter space with a large kitchen island, perfect for prep and socializing.brbrAll dishes, utensils, pots, pans, and serving ware included so you can cook and dine with ease.brbrAdjacent spacious dining room to gather around for memorable meals with family and friends.brbrRelax & Play: Indoor & Outdoor LivingbrbrLiving Room: Comfortable seating with a smart TV and streaming capabilities for your favorite shows and movies.brbrOutdoor Pool: Dive into your private heated pool (optional heating in winter months), a refreshing oasis to beat the Florida sun.brbrScreened Lanai: Dine al fresco or simply relax without worrying about bugs — perfect for morning breakfasts or evening cocktails.brbrOutdoor Play Area: A safe, fenced yard where kids can play and adults can unwind in the covered seating area.brbrGrill: Fire up the outdoor grill for fresh seafood, steaks, or veggies as the sun sets over the Keys.brbrBoating & Fishing ParadisebrbrFor boating and fishing enthusiasts, Reel Escape is a dream come true:brbrOwner’s personal watercraft occupies the lift but does not interfere with guest boat access.brbrThe property boasts quick, direct access to both the Gulf of Mexico and the Atlantic Ocean via a deep water canal, offering some of the best fishing, snorkeling, and lobster hunting in the Florida Keys.brbrDedicated storage room for fishing gear, plus a bait and ice freezer for your convenience.brbrAdditional Amenities for a Carefree StaybrbrHigh-speed, free WiFi to stay connected or work remotely.brbrIn-unit washer and dryer for laundry convenience during your extended stay.brbrAir conditioning and heating to keep the climate comfortable year-round.brbrFresh linens, towels, and toiletries provided for all bedrooms and bathrooms.brbrFully fenced grounds ensuring privacy and security.brbrPlenty of parking space for multiple vehicles.brbrImportant Rental Policies & DisclosuresbrbrMinimum Stay: 28 days minimum, as per Monroe County rental restrictions.brbrPets: Pre-approval required for 1 dog up to 50 lbs. Pet fee of $20/day applies and reduces total occupancy by one person. Fees must be paid prior to check-in.brbrPool Heating: Available November 15 – May 15 at $20/day, arranged before arrival. Pool heat not included in base rental rate.brbrBoat Lift Use: No lift usebrbrYour Florida Keys Adventure Starts HerebrbrWhether you’re planning a family reunion, a fishing expedition, or simply seeking a relaxing retreat surrounded by natural beauty, Reel Escape in Summerland Key delivers an exceptional experience. From luxurious indoor comforts to unparalleled outdoor amenities, this home is the perfect base for exploring all the Florida Keys have to offer.brbrWe look forward to hosting you and making your stay truly unforgettable!

REEL ESCAPE - 4 Bedroom / 2 Bathroom w/ Pool, Boat Dock & Sleeps 8!

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$449.68

Welcome to Sunset Serenity – Your Open Water Escape in the Lower Keys! brbr brbrUnwind in paradise at Sunset Serenity, a stunning 3-bedroom open water home on Summerland Key offering incredible views, tropical breezes, and the ultimate in relaxation. Perfectly positioned between Key West (35 minutes) and Marathon (30 minutes), this peaceful retreat puts you within easy reach of all the excitement while offering a serene setting to recharge. brbr brbrStep outside to your own slice of the Keys with sweeping open water views that greet you from the moment you arrive. Whether you're sipping morning coffee on the waterfront deck or catching breathtaking sunsets in the evening, the beauty of the surroundings never gets old. Enjoy the gentle sea breeze, watch passing boats, and let your worries drift away. brbr brbrBoaters will love the convenience of private dockage, giving you quick access to world-class fishing, snorkeling, and diving in the surrounding waters. brbr brbrWith two separate living areas, this beautiful home is ideal for families traveling together or multi-generational guests who want to enjoy time together while still having their own space. Best of all, your well-behaved dogs are welcome, so no need to leave your furry family member behind! brbr brbrWhether you’re boating, relaxing, or gathering with loved ones, Sunset Serenity is the perfect home base for your Florida Keys adventure. brbr brbrSLEEPS MAXIMUM OF 8 GUESTS (there are no interior stairs between levels, only access is via exterior stairs): brbr brbrBedroom 1 (Upstairs): King Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 2 (Upstairs): Queen Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 3 (Downstairs): Two Twin Beds brbr brbrLiving Room (Upstairs): Chaise Sofa, Chair, Smart TV (no cable/satellite TV) brbr brbrLiving Room (Downstairs): Chaise Sofa, Sofa with Pull Out Full Bed, Chair, Smart TV (no cable/satellite TV) brbr brbrKitchen (Upstairs): Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- 60' of Waterfront, ~30' of dockage (boat lift not available for guest use) brbr brbr- Saltwater Pool (heated to ~85 degrees Nov-Apr) brbr brbr- Fish Cleaning Station w/ Water brbr brbr- Outdoor Seating brbr brbr- Two Propane BBQ Grills brbr brbr- Bait Freezer brbr brbr- Ice Machine 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 brbrPet Policy: Up to two friendly and well-behaved dogs 50 LBS or less each 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. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

Sunset Serenity – 3BR Open Water Oasis On Summerland Key Boat Dockage, Stunning Views & Pet Friendly

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$246.3

Summary:brbr4 bed/2 bath canalfront getaway on Ramrod KeybrbrbrbrThe Space:brbrWelcome to Casa Playa, your spacious 4-bedroom, 2-bathroom retreat nestled in the serene beauty of Ramrod Key. This inviting vacation home is perfectly suited for families or friends traveling together, offering separate living areas for added comfort and privacy.brbrbrbrStep inside to discover a thoughtfully designed layout, featuring two bedrooms upstairs and two bedrooms downstairs. Upstairs, you'll find a cozy queen bed and a set of full bunk beds, providing ample sleeping arrangements for guests of all ages. Downstairs, enjoy the comfort of a king bed and a queen bed, one with a trundle, ensuring a restful night's sleep after days of adventure in the Florida Keys. There is high-speed Internet/WiFi and smart TVs in the living areas. Bring your own streaming services.brbrbrbrRelax and unwind on the large deck along the canal at ground level, where you can soak in the tranquil surroundings and perhaps even catch glimpses of local wildlife. For elevated views, head upstairs to another deck, offering a perfect spot to sip your morning coffee or enjoy evening cocktails under the stars.brbrbrbrPlease note that boat length is limited to approximately 18 feet, as the owner's boat will be on the lift throughout your stay. However, this restriction doesn't detract from the enjoyment of the waterfront lifestyle. Fire up the charcoal grill for a delightful outdoor cooking experience, perfect for grilling up the catch of the day or enjoying a leisurely barbecue with loved ones.brbrbrbrCasa Playa invites you to experience the laid-back charm and natural beauty of Ramrod Key. Book your stay today and create unforgettable memories in this cozy vacation rental on the Florida Keys.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. Occupancy is limited to a maximum of 8 people, and all overnight guests need to be registered with the property manager. No smoking. There's a cap on electric ($300) and water/sewer ($200).

Casa Playa | 4 bed/2 bath canalfront getaway

Summerland Key, Florida, United States

4

Bed

Bath

8

Sleeps

$195.32

Discover this delightful 2-bedroom house in Summerland Key. Guests will find a comfortable king bed and queen bed, plus a sofa bed in the living room for extra sleeping space. Two bathrooms offer convenience, each featuring a refreshing shower and a handy hair dryer. The living room provides a cozy spot to relax after a day of exploring. With excellent climate control, guests stay comfortable no matter the season. This fabulous home invites you to unwind and enjoy a peaceful retreat. We think our place will help you experience everything Summerland Key has to offer.

Waterfront Escape Near Key West

Summerland Key, Florida, United States

Bed

Bath

7

Sleeps

$254.76

Summary:brbrCanalfront 2 bedroom retreat on Ramrod Key with brand new dock!brbrbrbrThe Space:brbrWelcome to L’archipel, a charming, newly remodeled monthly rental that offers an ideal retreat for those seeking a relaxing getaway in the Florida Keys. Nestled on a serene canal, this property is a haven for water enthusiasts and nature lovers alike. With 2 bedrooms, 1 1/2 baths, and a host of modern amenities, this home promises a comfortable and enjoyable stay.brbrbrbrAs you step inside, you'll immediately notice the newly updated interior and furnishings. The living area is bright and airy, providing the perfect space to unwind after a day of exploring the Lower Keys or enjoying water activities. The fully equipped kitchen is a delight, featuring stainless steel appliances, granite countertops and ample cabinet space. Prepare delicious meals and savor them at the bar with seating for 4 or outside on the screened porch.brbrbrbrThe two bedrooms are thoughtfully appointed to ensure a restful night's sleep. The primary bedroom boasts a comfortable queen-sized bed, while the second bedroom features a queen bed and a twin-bed bunk set — perfect for small families or friends traveling together. Both bedrooms are tastefully decorated and offer plenty of storage for your belongings.brbrbrbrPower boaters will love the brand new dock! Bring your own boat or rent one locally to explore the surrounding waters at your leisure. Spend your days fishing, paddling or simply basking in the warm Florida Keys sun.brbrbrbrWhen you're not out on the water, take advantage of the covered screened porch. Enjoy alfresco dining or simply unwind while admiring the views of the canal. The property also offers ample parking space for your convenience.brbrbrbrThis monthly rental offers a tranquil and secluded setting while still being within easy reach of local attractions. Explore nearby Bahia Honda State Park, known for its pristine beaches and excellent snorkeling opportunities. Key West, with its vibrant nightlife, shopping, and dining scene, is just a short drive away, allowing you to experience the best of both worlds.brbrbrbrBreezeswept Beach Estates is a quiet neighborhood on the ocean side halfway between Key West and Marathon. Ramrod Key has a small commercial district to make your stay even more convenient: Boondocks Grille & Draft House and Miniature Golf, Looe Key Reef Resort's tiki bar and restaurant, Five Brothers Grocery Two, and a gas station/convenience store. The Key West city bus stops on the island on its way between the Southernmost City and Marathon and offers several stops along the way.brbrbrbrWhether you're seeking relaxation or adventure, L’archipel provides the perfect base for your Lower Keys vacation. Book your stay today and create lasting memories in this newly remodeled canalfront retreat.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 overnight guests need to be registered with the property manager. No smoking. There's a cap on electric ($250) and water/sewer ($150).

L' archipel | Brand new dock!

Summerland Key, Florida, United States

Bed

1

Bath

Sleeps

$819.84

Summary:brbrVilla Jekjak- 4 BDR, luxury residence with pool & beachbrbrbrbrThe Space:brbrEnjoy the unobstructed 270-degree ocean view in this newly renovated beachfront residence. Located in the most exclusive part of Cudjoe Gardens this 2- story house is surrounded by the water on 3 sides. Three bedrooms and two bathrooms are impressively decorated in a soft coastal palette and are located on the second main living floor.brbrAmble of natural light emphasizes the open and easy-flowing design of the main floor. Well-equipped chefs kitchen has top-of-the-line appliances and is a perfect retreat for culinary-inspired guests.brbrHighlighted by the walls of glass doors, Family Friendly floorplan combines the living room, dining room and opens to the oceanfront terrace. The vaulted ceiling adds great drama to the space.brbrLight & Airy Master Suite features King Bed, a private Master Bathroom with a stand-up shower, and a large walk-in closet.brbrThe guest wing offers generously scaled 2 bedrooms and a shared bathroom.brbrThe downstairs Guest Quarter enclosure has an additional private queen bedroom, rec room, TV area, and a wet bar and full bathroom.brbrThe private pool is nestled on a sandy beach and surrounded by meticulously maintained grounds. Deep access to world class fishing and free dockage makes this house a boaters paradise!brbrThis house is truly Paradise Found!brbrThe property is PET-friendly with a non-refundable PET fee.brbrbrbrAdditional features:brbrWasher & DryerbrbrCentral AC & ceiling fans throughoutbrbrStarter supply paper productsbrbrStarter set cleaning productsbrbrLinens, bath, and pool towelsbrbrKitchen cookware, dishes, flatware, glasswarebrbrWireless high-speed internetbrbrFully fenced private residencebrbrHousekeeping services availablebrbrOriginal ArtbrbrPrivate dockbrbrPrivate Beach and a hammockbrbrOutdoor ShowerbrbrbrbrBEDROOMSMaster- King BedbrbrGuest Bedroom #1- Queen BedbrbrKids Room- Bunk BedbrbrDownstairs Guest Quarter- 1 Queen Bed

Villa Jekjak

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$308.79

Set on the beautiful Sugarloaf Key, our house will offer you comfortable living in the most friendly of communities. brInside there are three bedrooms. One King with en suite. Two further bedrooms with Queen beds and further bathroom. Each bedroom has a TV. There is a large kitchen with all facilities you would need including a dishwasher, washing machine and dryer. The comfortable lounge has fabulous views down the canal. The Wi Fi is fast and there is a printer if needed. Working from here is easy!brOutside living is what its all about with comfortable seating and dining furniture, grill, fridge freezer and W.C. brThe Wooden Swimming Platform can accommodate a small boat and provides access to our crystal clear swimming canal. brDownstairs is fully lit so enjoy your warm evenings drinking cocktails with a wonderful view.brThe large plot has plenty of room for any vehicle or boat that you travel with. brWith superb bars and restaurants a short drive away, you can mix with the locals or take the 20 min drive into Key West. Sugarloaf Marina is 2 mins away for all your boating needs including a public ramp. Easy access to the Sand Bars brCome and immerse yourself in local life- fabulous neighbours who will make you most welcome!

Stunning Sugarloaf, 3 bed house on huge plot to accomodate your RV or boat.

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$231.78

28 consecutive day minimum rental. Lower Keys Living at its very best. This This Modern 1,700 sq ft Old Florida Keys Waterfront House is located on Lower Sugarloaf Shores at Mile Marker 17, a half mile off of US 1 in an extremely quiet neighborhood and is available for 28+ day rentals. It is a three bedroom, three baths elevated house. All of the bedrooms are located on the second floor with two full bathrooms. Each bedroom has a queen size bed, closet, dresser, nightstand and TV. The bathroom in the master bedroom has a shower/tub. The second bathroom has a shower only. The third bathroom is conveniently located on the ground floor in the garage. This is a great vacation property, not a party house... This house is completely furnished with everything you will need for your vacation stay. The Full-sized kitchen has a beautiful granite countertop and is complete with a glass top stove, microwave, dishwasher, refrigerator/freezer and garbage disposal. A complete collection of cookware and flatware is provided. All of the essential linens and towels are provided and there is a full-sized washer and dryer available downstairs. TVs and Wi-Fi are provided in every room. Every TV is supported with a fire stick to access your streaming services. There is no Cable TV coming into the house. brbrThere is a spacious 40’ x 15’ screened in lanai overlooking the waterfront with canal and bay views. For your comfort, there is a trestle table and benches for a relaxing morning coffee or outdoor dining any time of the day. There is also a couch and comfortable chairs for conversation or a glass of wine. The walk around balcony surrounding the house provides a view of the entire property without having to leave the second floor.brbrThe house is located on a crystal-clear deep-water canal that's great to swim in with 100’ of dock space and overlooks a beautiful bay. This wonderful location allows access to the Gulf of Mexico with world class back water fishing, as well as the Atlantic Ocean with fantastic patch reefs and deep water fishing in the Gulf Stream. Beautiful reefs in the Lower Keys provide some of the best diving and snorkeling in all of Florida. A word of caution, the waters in Sugarloaf Key can be shallow in areas, so navigational care and a good understanding of the local waterway is required. For your recreational enjoyment there are ocean kayaks and bicycles available for use. There is a gas grill, beach chairs and umbrellas.brbrLocated halfway between historic Key West and Big Pine Key with its endangered Key Deer. Both are good for shopping and restaurants. Grocery shopping is within minutes of the house. Key West is also very popular for its night life, museums, beach, airport as well as many other attractions.brbrThis family friendly, and pet friendly house is used frequently throughout the year by the owners and is being offered for rental to those who are willing to care for it as much as we do.

Sugarloaf Shores Wide Canal 3/3 Waterfront w/ 100 ft Seawall in Quite Community.

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$465.4

Indulge in the ultimate tropical escape at Bayside Beauty, a stunning 3-bedroom home nestled in the exclusive South Point neighborhood on Lower Sugarloaf Key!br brPerched along the shores of Sugarloaf Sound, this luxurious vacation rental offers unrivaled panoramic views that paint an enchanting picture of paradise. Step into your own private oasis, where the allure of the Florida Keys comes alive. The expansive living spaces seamlessly blend with the breathtaking outdoor scenery, creating an ambiance of tranquility and luxury. With a design inspired by the tropics, Bayside Beauty is a true haven for those seeking relaxation and rejuvenation. The highlight of this retreat is the private 60 ft. grotto-style pool, adorned with a magnificent sailfish fountain, offering a unique and refreshing swimming experience. Lounge on the spacious deck, basking in the warm sunshine, or take a dip in the pool to cool off while enjoying the serene surroundings. Located a mere 25 minutes from the vibrant energy of Key West and 45 minutes from the charming town of Marathon, Bayside Beauty is perfectly situated for those seeking both adventure and relaxation. Immerse yourself in the local culture, savor delicious cuisine, and explore the unique attractions of the nearby islands. Escape to Bayside Beauty and experience the perfect blend of luxury, natural beauty, and convenient access to the best that the Keys have to offer!br brSLEEPS A MAXIMUM OF 8 GUESTS:br brBedroom 1: King Bed, En-Suite Full Bathroom, Flat Screen TVbr brBedroom 2: King Bed, En-Suite Full Bathroom, Flat Screen TVbr brBedroom 3: Twin/Full Bunk Bed, Twin Bedbr brLiving Room: Sofa, Loveseat, Two Chairs, Flat Screen TVbr brKitchen: Nicely equipped (all things necessary to prepare and serve a meal)br brAMENITIES:br br- Saltwater Heated Pool (Heated to ~80 degrees Nov-Apr)br br- 60' Waterfront (limited boat dockage, owner's boat stored on boat lift)br br- Fish Cleaning Station with Waterbr br- Outdoor Seatingbr br- Propane BBQ Grillbr br- Parking for a maximum of 4 vehicles (including boat trailers) on the property. Recreational Vehicles may not be parked on the property.br br- Linens and towels providedbr brThis is a non-smoking home. This home is a 28-day minimum rental per Monroe County Code. The security deposit on the quote also includes utilities which consist of electric and water.

Bayside Beauty, 3 bedroom with pool

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$232.76

Located on beautiful Summerland Key, this is the perfect vacation home for any family. Just 20 minutes from Key West and minutes from Looe Key. Enjoy the private pool and large sun deck for BBQing or relaxing. Canal access is perfect for kayaking and there is only a 10 minute boat ride to the ocean. A canoe and Four kayaks are provided for vacationers (2 adult and 2 childrens kayaks) as well as use of kayak dock, fish cleaning table, and bait freezer. The kids are sure to be entertained by the private air strip located on the street side of the home. All linens are provided and other amenities include table tennis, cable television, internet, central A/C and washer & dryer. Please call or email with all your vacation stay requests.

Relax at the flying hogfish

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$322.95

Hello ! My name is Debra and I run our VRBO account for our family. We love our salty slice of paradise and I look forward to sharing it with you!brbrOur oceanside 3/2 home features a large lot, 200ft of concrete dockage, fish cleaning station, & plenty of parking for boats, cars & trailers. You will have a full kitchen, living & dining room, TV, wifi, screened porch, tiki hut & plenty of outdoor space to fish, play, kayak, and Florida Keys sunsets. Quick boat access to both Atlantic & Gulf.brThe spacebrOur house offers seclusion, privacy and plenty of room to play, perfect for you and your family to relax & unwind. We have a large double lot with Tiki Hut and 200' of concrete seawall and dockage for all of your toys. Fish right off our seawall, take a dip in the canal, relax and float, or go kayaking and explore.brbrWe have a fisherman's paradise here. A deep water canal that quickly takes you directly out into the Atlantic and quickly over the reef to experience the world's best fishing ! There is a public boat ramp, fuel, bait and snacks (Cudjoe Gardens Marina) located about 7 minutes away, and about a 10 minute boat ride back to the house. Cudjoe Sales is 2 minutes away for tackle and specialties as well as Low Key Fisheries, the perfect place to buy daily fresh caught fish, lobsters and stone crab.brbrDining out Gotta try Boondocks about a 5 minute car ride. Live entertainment every night, and a Putt-Putt Golf course too. Square Grouper, fine dining at it's best is only 2 minutes away. Winn Dixie, Walgreens and CVS is only 10 minutes away.brbrNo chance of getting bored !! By boat you are about a 20 minute ride to Looe Key reef, and 10 minutes to American Shoal reef. Two of our favorite places to go every time we come down. The grandkids LOVE it.brbrNo boat No problem. Reserve a Looe Key boat tour, You will NOT be disappointed. It is breath taking. And a 15 minute drive to Bahia Honda State Park for a picnic on the beach with gorgeous emerald waters to enjoy snorkeling, fishing and relaxing on the beach, and their nature walk is awesome. You are only 5 minute walk to Kemp Channel bridge to enjoy fishing off the bridge.brbrAnd you can't go to the Florida Keys without a trip to Key West. Just a short and scenic 20 minute drive and you in the world famous Key West. Discover the historic Conch Republic, schedule a tour to visit the Dry Tortugas National Park (one of my favorites), and have a drink on Duval Street while you take in the world famous sunsets.brGuest accessbrThe entire upstairs of house is yours we just ask that you respect and love it (and all the wildlife that you may come across) as if it was you own.brOther things to notebrWhen requesting a booking please specify the following:br1. How many people, names and ages of each.br2. How many (if any) watercrafts you will be bringing with you.br3. No smokingbr4. No pets

Waterfront Oceanside 200' Seawall 3/2 Sleeps 6

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$264.77

Private 1 acre property nestled in Little Torch Key, this unique property offers a pleasant retreat for a couple looking for peace, space and outdoors. This property offers 1 king bedroom 1 full bath, living room, dining room, kitchen, and office with a cozy sofa bed in the main house. 1 queen bedroom 1 full bath under the main house with a screened in florida room TV and sofas. Laundry room with storage and extra refrigerator all under the main house. A detached guest house that makes up the third bedroom and bathroom on this property which consists of 1 queen bed and 1 full bathroom, sofa and TV, with a screen porch upstairs and screened in florida room underneath and commercial ice machine. Guest house and Main house all located on 1 acre property. Every couple or family member will have their own space for comfort. The property offers a fully fenced in yard with gates, screened in porch upstairs out the back door with stairs that lead you to the lower pool deck with table, chairs and loungers just off the above ground pool. Large yard with plenty of parking. Property located on a boatable canal to accommodate up to a 25-foot boat and within 10 minutes to closest grocery store. We hope you will enjoy the peacefulness and relaxing time we have spent on this property. It is truly a very unique property in this area.

Private 1 Acre property outdoor retreat on boatable canal- Monthly Rental!

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$448.63

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrIntroducing Casa Rosada, a delightful canal front haven nestled within the enchanting Cudjoe Gardens on Cudjoe Key! brbr brbrOffering an invitation to tropical relaxation, this charming abode provides a tranquil escape from the everyday. Dock your boat along the seawall and embark on fantastic fishing escapades in the pristine waters of the Atlantic or the Gulf, a mere stone's throw away. Rejuvenate with a refreshing dip in the inviting pool, cocktail in hand, as boats gracefully pass by, adding to the serene ambiance. While Casa Rosada offers a plethora of activities to enjoy, including its own array of offerings, if you're enticed to explore the wonders of the Keys, the vibrant allure of Key West awaits a convenient 30-minute journey, while the captivating charm of Marathon beckons within the same short span. Unveil the essence of island living at Casa Rosada! brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1: King Bed, En-Suite Bathroom, Smart TV brbr brbrBedroom 2: King Bed brbr brbrBedroom 3: Two Twin Beds brbr brbrLiving Room: Sofa, Chair, Flat Screen TV brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- Private Heated Pool (heated to ~85 degrees Nov-Apr) brbr brbr- 85' of Seawall (Davits are not for guest use) brbr brbr- Fish Cleaning Station with Water brbr brbr- Tiki brbr brbr- Outdoor Seating brbr brbr- Electric BBQ Grill brbr brbr- Hamilton FlexBrew (drip & single serve), Toaster, Blender brbr brbr- Parking for a maximum of 4 vehicles (including boat trailers) on the property. Recreational Vehicles 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 brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. 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.

Casa Rosada: Cudjoe Gardens Canal Front Retreat, Pool, Tiki, Deep Dockage & Rapid Open Water Access!

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$326.83

Atlantic Chateau, is a beautiful 3 bedroom 2 bath house on Cruikshank Island. Cruikshank Island is a peaceful private island off East Caribbean Drive, Summerland Key Florida only a 20 minute drive to Key West for a night on the town.brEnjoy the gorgeous sunsets in the evening while relaxing on the porch where the tropical breezes flow through or relax by the new pool & spa. The house is tastefully furnished for your comfort. Spacious kitchen to cook your lobsters and fish. brbrKeywords: Beautiful Sunsets from this property located on private island only 25 miles from Key West. Excellent boating,20 foot deep canal,150 foot dock, 5 mins by boat to open waterbrRent Rate Per Month inc utilities pool/spa heating not includedbrbr** This is a 28 day rental ** Must Rent from the 1- 30/31. Can not separate months, unless prior arrangements have been made.brPool Heater fee for the month is $250.00

Summer Month's Just Opened Up!!! Canal Front Pool Home in Summerland Key

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$334.17

MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Booking from the 1st of the month. Waterfront house with heated pool. Located on the canal of Summerland Key, has a 60 ft dock. Short access to Atlantic and Golf side. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Open kitchen concept with quartz countertops, stainless steel appliances, and an eat in kitchen island, separate dining room.Outdoor chest/bait freezer and ice maker provided, fish cleaning station,2 kayaks with paddles.Pet fee $150

Florida keys Waterfront,Forever Summer

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$343.13

Captivating views from sunrise to sunset overlooking expansive salt ponds and open water from this newly renovated 2-story, waterfront home. This waterfront Little Torch Key home is situated on a tranquil corner lot in the Mates Beach neighborhood. This home has been stylishly upgraded and features a spacious free-flowing floor plan with granite countertops and stainless appliances. The views from every window will make you feel like you're in paradise at each glance. After a day on the water, dock your boat at the new concrete dock and enjoy your fresh catch on one of the many spacious wrap-around decks overlooking the canal and salt ponds. 2 charming guest bedrooms will greet your guests with a sun-filled welcome and a private door in each leading out to a relaxing deck. The massive owner's suite comes complete with a large, private balcony with open water views, offering an oasis of peace and relaxation. The natural light floods the ensuite spa-like bathroom, featuring a soaking tub, large walk in closet and custom tile shower. Just a short boat ride awaits world class fishing, diving and boating. Relax on a nearby sandbar like the content keys or picnic island or explore nearby Looe Key National Marine Sanctuary.brbrThe Pool was completed in 2024 and is a salt water system complete with a heater for those cold months and a chiller for those hot summer days. The two waterfalls provide calming sounds and even provide a little massage when you stand under them. The deep end hosts a cocktail bench for the big kids while the shallow end has a sun shelf for tanning or the little ones to play safely. Enjoy the light show as the colored lights provide a fun atmosphere. brbrThe lower level has a 500lbs/day commercial ice machine so no more running into town before those fishing trips. A bait freezer to store as much bait as you could need. And a Pit Boss smoker to cook the day’s catch. You will also find power and water at the dock for your boat needs. Additionally there is a 100 gallon fuel bulk tank with a 12 V pump to save you time and money by getting a fuel truck straight to the house.brbrEnjoy after hours with drinks around the fit pit table or make s’mores with the kids. The private font swinging porch with twinkling lights also makes for a great after hours hangout. brbrBikes are available to cruise around the neighborhood, to Kiki’s bar or up and down the many bike paths. Two kayaks and paddle board are also included a short paddle will get you into the salt flats and neighboring bird sanctuary.

New pool & Huge master suite! Open water views , 2 stories of wrap around decks

Summerland Key, Florida, United States

Bed