Vacation Rentals By Owner In Summerland Key, FL

This classic keys cottage is tucked among the palm trees on the open water of Niles Channel. Enjoy the breath taking sunrises and romantic moonrises, seabirds,dolphins and a nearly south-easterly breeze. This lovely hideaway is next to last home on dead end street, this 2 BR, 2 bath ground level home has a large kitchen and Master suite. This great location is only 30 minutes from historic key west.

Cottage

Peaceful ocean front cottage.

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$501.21

Beautiful home on the oceanside of Summerland Key on a protected deep water canal one lot in from the ocean. 45' seawall will accommodate boats up to 40' in length and 5' in draft. Direct Ocean access to great offshore/backcountry fishing and reef diving/snorkeling that are literally minutes away. The property features spectacular ocean views, a private in-ground heated pool with a paver lounging area, a Tiki Hut, cable TV, a washer and dryer, a gas barbecue grill, and more! brbrOpen concept living with a nicely appointed kitchen with all the appliances and conveniences necessary for a great stay along with a large 8-seat center island for cooking and dining. Entertainment with a 70 TV and bar buffet hosting all the supplies you will need. The downstairs deck also has lovely ocean and sunrise views. brbrNewly remodeled upstairs master suite has incredible sunrise views from the king-size Sleep Number bed. A new master bathroom with sun-filled ocean views while you brush your teeth and a walk-in shower with three shower heads. Off the master suite offers views that go on for miles and the sunrises are spectacular. An additional ensuite has been added to the upstairs guest bedroom featuring a walk-in shower, comfy king-size bed, and closet. One downstairs bedroom features a king size and the other features a queen bed. The downstairs bedrooms share a lovely bathroom with a shower and tub. brAll bedrooms have cable TV and wireless internet. brbrKey West is less than 1/2 hour away by car and offers great shopping, dining, entertainment, and nightlife. This is an exceptional property that has all that you will need to enjoy a fantastic vacation in the Florida Keys!brbrMonroe County prohibits vacation rental homes from renting their home for less than 28 nights.

Solstice Seaside Waterfront House w/Pool & Spectacular Ocean Views/Min 28 Nights

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$346.07

Lovely ocean front updated lower Keys home in Summerland / Ramrod Key, beautiful open water views, spectacular sunrises, great Paddle boarding Kayaking and shallow draft access boating right from the private dock. 2 Master Bedrooms, 2 full baths home with minutes to great fishing, snorkeling and diving. Office with a view along with a second desk work station available from the upstairs master bedroom. Grilling, dining and relaxing in the gated backyard on Newfound Harbor and the Atlantic open water. Close to Key West-35 minutes, nearby Looe Key Reef and marine sanctuary, and the Bahia Honda State Park only 15 minutes. For boating in the area there are a wide variety of captained excursion boats available or nearby rentals if you don’t have your own boat available. 2 person Kayak included. brMonthly discount included.

Keys cottage, oceanfront, dock, fenced backyard

Summerland Key, Florida, United States

Bed

Bath

4

Sleeps

$152.38

Welcome to your dream canal front RV Lot with peekaboo ocean views. Situated on a quiet cul de sac, this picturesque lot beckons with its idyllic setting and abundant amenities. As you arrive, you're greeted by 30 feet of prime dockage with a step down concrete seawall, providing easy access for your watercraft adventures and with 69' feet there is plenty of space to fit most Recreational vehicles. Included, a convenient fish cleaning station, water, sewer, and electric hookups available, including 30, 50, and 110 amp service. This lot ensures effortless comfort during your stay. Whether you're seeking a weekend getaway or a long-term retreat, this canal front RV lot offers the perfect blend of convenience, comfort, and natural beauty. Located in the Venture Out gated community This Lot offers an array of amenities to enhance your lifestyle, including tennis courts for friendly matches, playgrounds for the little ones, and a heated pool and jacuzzi for year-round relaxation. Launch your boat effortlessly from the community's boat ramp, and stock up on essentials at the on-site store for all your adventures on the water. Located in Cudjoe Key, this RV lot offers more than just a waterfront haven— Indulge in delectable dining experiences at Square Grouper Restaurant, My New Joint Cocktail Lounge, and the cozy ambiance of Morning Joint Coffee all just a short drive away. Explore the local favorites nearby, including the savory offerings of the Bent Prop, laid-back atmosphere of Tonio's seafood shack and Tiki Bar, and family-friendly fun at Boondock's Mini Golf and Draft House. Whether you're seeking tranquility by the water's edge, thrilling aquatic adventures, or mingling with the locals at favored hot spots, this RV lot has everything you've been searching for to ensure your best Florida Keys adventures. **No cable or WIFI service is provided at this site** Please note that a Registration/Check-In Fee of $125 (subject to change) will be charged by Venture Out upon arrival. Additionally, parking is provided for one vehicle per unit, with the possibility of obtaining an extra parking permit at the Guard Station for an additional nightly fee, subject to availability and a maximum stay of 14 days. It is essential to adhere to all the community's Rules and Regulations during your stay to ensure a harmonious experience for all residents and guests. To comply with county and state regulations, proper taxes are collected regardless of the booking platform used. Renters must be 25 years or older, and overnight occupancy is limited to a maximum of 6 people, all of whom must be registered with the Rental Manager and Venture Out. Venture Out Regulations allow for up to 2 dogs per lot, providing the perfect opportunity to bring your furry companions along for the adventure. Check-in time is at 4pm, and check-out time is at 10am unless alternative arrangements have been made with the Rental Manager prior to arrival. To safeguard both guests and the property owner, a refundable $150 Security Deposit is required at the time of booking. A 4% credit card processing fee will be applied if paying with a credit card. Immerse yourself in the laid-back charm of Cudjoe Key and make the most of your vacation by securing this inviting RV Lot. The main guest of the reservation will be required to submit a copy of your driver's license to the rental manager for our records. The Rental Agreement is required to be signed within 24 hours from time of booking. All reservations are subject to final approval from the local Rental Manager.

Caravan Park/Campsite

Canal Front RV LOT 451 Venture Out (40x23x70x31x35)

Summerland Key, Florida, United States

Bed

Bath

6

Sleeps

$1035.43

End each day with a breathtaking show as the sun sets over the horizon, painting the sky with a kaleidoscope of colors. The panoramic views from this home are nothing short of mesmerizing, providing a magical backdrop for evening relaxation or entertaining guests.br brWelcome to your ultimate vacation getaway! This beautifully renovated home is located on Sugarloaf Sound and offers everything you need for a perfect retreat. With 2,400 sq. ft. of luxurious living space on one level, this stunning property boasts four bedrooms and five bathrooms, ensuring plenty of space and privacy for everyone. The kitchen is open, well-appointed, and ready to make memorable meals. The living area is spacious and inviting, with plenty of room for everyone and a large-screen TV. Rest easy in beautifully decorated bedrooms boasting king beds that offer comfort and relaxation after a day of adventure. Each bedroom has a TV and a bathroom. All of the bathrooms have full-length mirrors, as well as makeup mirrors in the vanity.br brOutdoor living in the Florida Keys is a unique and exhilarating experience, making it a sought-after destination for those seeking sun, sea, and relaxation. The outdoor amenities at this home do not disappoint. Sip cocktails or enjoy a meal under the Tiki Hut, a perfect spot for socializing or unwinding with a book. Dive into the refreshing, heated, & chilled pool whether you want to cool off on a hot day or enjoy a warm swim under the stars. Explore the stunning waterways at your doorstep in one of the kayaks. Paddle through serene waters and soak in the natural beauty surrounding you. There is ample outdoor furniture to unwind and enjoy the gorgeous views and stunning landscaping.br brThis house is designed for relaxation and adventure, offering luxurious amenities and unbeatable views. Whether you're lounging by the pool, exploring the water by kayak, or simply soaking in the beauty of your surroundings, this is the vacation experience you've been dreaming of.br brBook your stay now and create unforgettable memories in this sunset paradise! Your perfect vacation awaits.

Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool

Summerland Key, Florida, United States

4

Bed

5

Bath

8

Sleeps

$711.52

Welcome to Paradise at the End of The Road. This home is so secluded you will think you are on your own private island. We feature water views from every room and window, even the laundry room. Completely redone following hurricane Irma, everything is new, updated and designed for relaxation, luxury, and the ultimate fishing experience.brbrIndustrial Ice Maker is located downstairs to keep all of your coolers filled! brbrThe property is gated with ample parking for cars and boat trailers. A large heated pool, hot tub and out door bath house sit surrounded in a luxury tropical garden featuring over 200 orchids, and fruit trees for you to enjoy. Pool side features a bar, dinning table, lounge chairs, Green Egg , gas grill, and TV. We also feature a mosquito misting system and corner fans to keep you cool and bite free. Also located down stairs are additional refrigerators and freezers to make out door dinning and cooking a breezebrbrThe boat dock, on niles channel, features a 16,000 lb lift, 2 slips, fish cleaning station, and underwater lights perfect for night fishing. A brick path runs along each side of the dock to the water to make putting in kayaks easy. Easy access for large boats. brbr2 kayaks, 2 versa boards, and 2 bikes are available. brbrAlthough you feel like you are on an island, you are a quick bike or car ride up the road where restaurants and shopping can be enjoyed. brbr3 King beds, 2 queen and 2 twin beds. Every room can access the walk around porches where lounge seating is available. Wireless internet and direct TV is also provided. First floor- 1 bedroom w/ 2 kings/ private bath. 1 bedroom w/ 2 twins. 2 bedrooms each with a queen bed. 2nd bathroom. All rooms have access to wrap around porch. 2nd floor is living dinning with a half bath + laundry & the master bedroom/bathroom. All rooms open to wrap around porch. Water views from every room and chair! brbrKey deer, dolphins, turtles, birds, and tropical fish are often seen at this piece of paradise.

Waterfront Sunrise & Sunset Full Views! Pool, dock, lift, Industerial Ice Maker

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$1151.72

THE POOL MAY BE HEATED FOR AN ADDITIONAL FEE OF $25 PER DAY OF STAYbrThis is a newly remodeled four bedrooms elegant house. The property located in the heart of Summerland Key. It is the perfect Key for a vacation getaway. Summerland Key is an island in the lower Florida Keys about 20 miles east of Key West. The island has a private airport located 3 blocks from the house. The airport can be used by the guests of the house. Summerland is the perfect spot for fishing, hiking, boating, kayaking, and cycling. There is an oceanfront pool, where you can soak up the sun just steps from the house all year round. Breathtaking views of the crystal blue ocean and sunsets can be seen throughout the property. Dine outside with island vibes under the tiki hut. The house also includes a billiards table in the carport. Disclaimer: THE DOCK is a solid steel located in a deep water canal with a 6' control draft, it was recently rebuilt.brLIVING AREAbrSpacious ocean viewing living room with designer furniture and a 56 flat -screen TV.brKITCHEN & DININGbrModern granite countertops with a full set of stainless-steel appliances. The kitchen has a microwave oven (no individual oven), coffee maker, toaster, dishwasher, french door refrigerator. Dining table with chairs (additional foldable commercial dining table available with 8 chairs) with a breathtaking view of the Atlantic Ocean.brbrWe do provide guests with a very basic toiletry starter kit.brbrBEDROOMS &BATHSbrThis two-story home sleeps up to 12 guests in four bedrooms.brThe first master bedroom on the first floor is furnished with a king-size bed. You can enjoy waking up to the view of the ocean from your room. It has an en-suite bathroom with a walk-in shower. brThe other bedroom on the first floor is furnished with one bunk bed (top bunk is an extra-large twin and the bottom bunk is extra-large full). There is also a twin-sized bed in the room. This room can sleep four guests. Right outside the door is the bathroom with a tub and shower.brOn the second floor, the elegant second master bedroom is furnished with a king-sized bed and a 56 curved TV. This bedroom has an en-suite bathroom with a walk-in shower.brThere is another bedroom on the second floor. The entrance is through the master bedroom. The fourth bedroom has one bunk bed (top bunk is an extra-large twin and the bottom bunk is extra-large full) and full sleeper. This room has gorgeous natural lighting and breathtaking panoramic views of the ocean. brOUTDOOR AREAbr House has a pool with a picturesque view of the ocean (The pool is professionally maintained and is serviced once a week. The pool is not heatted. We live in a National Wildlife Refuge. Wildlife, particularly birds, have a mind of their own and sometimes wind blows debris into the pool. You may need to skim the pool in between services. We highly recommend you do not feed birds and wildlife.). The tiki hut is the perfect setting for romantic outdoor dining. The pool is not heated. In the evening, the whole yard is illuminated with stellar lights. You can have a serene walk in the acreage yard.brThe outdoor grill comes with 2 propane tanks. ADDITIONAL REFILL ARE NOT PROVIDED. Multiple businesses in the area provide exchange or refill.br brEXTRA AMENITIES & MORE DETAILSbrThe amenities include complimentary Wi-Fi, washer and dryer, parking space for up to ten cars. The driveway is boat and trailer friendly. Street parking is also readily available.

One of the very few beach houses with a daily, rental license in the Keys.

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$514.54

This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atlantic. Sea Wall has room for (1) 24' boat. This home can sleep 7 adults and 2 small children. There are 4 bedrooms and 4-1/2 bath. Fully stocked modern kitchen, great out door space and a separate apartment for privacy. Swimming pool recently installed and complete.brThere are 3 Kayaks and 4 bikes included as well as a ping pong table.brbrYour property manager lives nearby and is available if you have any requests during your staybrbrQuite Residential NeighborhoodbrbrYou will be provided with check in instructions prior to your arrivalbrbrThe perfect home for a family gathering. With a total of 6 sleeping areas, you can spread out and have a space for your own private time.brThis home is located on a canal with boat dockage and has a tropical pool for cooling offbrbrUber, Lyft and Taxis area available as well as Public Bus transportation. It is recommended that you have a carbrbrPrior to your stay, we require you to complete a pre-arrival form and sign & agree to our rental conditions.

Mad Mahi Canal with pool.
This is a pet friendly home. A pet fee and approval of your pet is required.

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$462.59

VO220brKeys Home w/ 40' Dockage br2Bd/2Ba brThis beautiful home on stilts overlooks the open water with amazing views from dusk to dawn. Features in the home include two furnished bedrooms with two full bathrooms, well appointed with all the amenities one could ask for while on vacation! The main living room has french glass doors and large picture windows allowing the outdoors in and leads to a porch overlooking the water. The kitchen features lots of cabinets , countertop space and an island with seating for preparation of your favorite meals with stainless steel appliances such as microwave, dishwasher, range, oven and refrigerator with ice and water at the door, and full attention to small appliances and cookware. brbrThe master bedroom features a queen bed, flat screen TV, double closets, ceiling fan and private full size bathroom. The guest bedrooms features a queen bed, a flat screen TV, ceiling fan, closet, and access to hallway full size bathroom. brbrA boating dream location, the dock is equipped with heavy duty dock posts, fish cleaning table and cleats and offers immediate access to the ocean and gulf! brbrDownstairs is an open air patio with a spacious outdoor gathering area featuring a picnic table, BBQ and 4 new bikes. brbrSECURITY DEPOSIT REQUIRED, NO SMOKING, NO PETS,br7 DAY DURING MINI LOBSTER SEASONbrOVERFLOW PARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brVO REGISTRATION FEE $125.00- DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE..

Keys House - Venture Out Lot 220

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$223.8

Perfect fishing and boating location on Kemp Channel between Cudjoe Key and Summerland Key. New Pool Installed August 2024. Brand new Large pool to relax by when you are not out on the water. Fantastic quiet neighborhood wonderful for walking, biking, kayaking and relaxing. Great access to bike trail along US 1. Walking distance to a good coffee joint. Fully stocked kitchen. Newly Remodeled master bathroom! Bait freezer and refrigerator downstairs. Home has 75 feet of seawall that fits a boat up to 30 feet.

Canal Front Home Access to Kemp Channel Cudjoe Key New POOL!

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$847.78

Fabulous resort-style living & incredible open water views over Niles Channel at this 7 BR 5 BA home on Summerland Key. Just under an acre boasting a sandy beach w/pretty palms, large custom pool, & deep water dockage w/quick access to ocean, gulf & back country. The open Great Room boasts granite kitchen, wood floors & gorgeous water views.brbrYour property manager lives nearby and is available if you have any requests during your staybrbrVery secluded quite neighborhoodbrbrYou will be provided with check in instructions prior to your arrivalbrbrSpectacular property with 7 bedrooms and a resort style backyard. Private pool and Private dock for your boat.brPlenty of parking for your large group.brGourmet kitchen and large outside and inside dining areabrbrUber, Lyft and Taxis area available as well as Public Bus transportation. It is recommended that you have a carbrbrPrior to your stay, we require you to complete a pre-arrival form and sign & agree to our rental conditions.

Summerland Nest - Ocean view with private beach and pool

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$265.06

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to The Salty Sailfish, a magnificent canal-front home nestled on Cudjoe Key! brbr brbrWith updated furnishings and a commitment to relaxation, this beautiful retreat invites you to immerse yourself in the serene lifestyle of the Florida Keys. For the boating enthusiasts, your vessel will find a perfect spot along the sea wall, providing swift access to the outstanding fishing spots located just minutes away. Whether you're an avid angler or a leisurely fisher, you'll be in your element. Mornings at The Salty Sailfish are a tropical dream come true. Picture yourself sipping your coffee while the world awakens, or take a refreshing dip in the newly completed pool as boats lazily pass by. Your days here are infused with relaxation and tranquility. While there's plenty to do right at the house, the Keys beckon with their allure. You're only a 30-minute drive from the vibrant and eclectic charm of Key West, offering an array of activities and attractions. Alternatively, in just 25 minutes, you can find yourself in the heart of Marathon, discovering its unique treasures. Your experience here promises to be nothing short of exceptional. So, what are you waiting for Book your stay now and let the adventure begin! 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/Full Bunk Beds with Twin Trundle Bed, Smart TV (no cable/satellite TV) brbr brbrLiving Room: Two Sofas & Chair, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- Private Saltwater Pool (not heated, 24'x9', depth 4'-5.5') brbr brbr- 60' of Seawall (recommend boats 24' or less due to shallow exit from canal, especially at low tide) brbr brbr- Fish Cleaning Station brbr brbr- Bait Freezer brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Keurig, Drip Coffee Maker, 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 brbr- Elevator pictured does not work 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 (2) friendly and well-behaved dogs with a combined weight of fifty (50) 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 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.

The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$324.89

Your Sugarloaf Key adventure begins at this private tropical 2 bedroom canal front house at Milepost (MP) 17. Experience the always adventurous downtown Key West just 20-25 minutes away or choose to stay at your own private oasis and lounge in the chilled/heated pool under the waterfall, hang out in the tiki hut with a beverage and your favorite book. Bring your boat, kayak, scuba and go exploring from your back yard amongst the mangroves.brbrThis cozy retreat offers superb comfort for guests. The ground level offers outdoor living while the upper level features the bedrooms, open concept living room/kitchen/dining area and screened in porch. The kitchen is fully stocked with tools needed to prepare and serve a meal. Each bedroom features a king size bed and a sliding glass door with a view of the extensive tropical landscaping. The MBR has an ensuite bathroom with a large walk-in closet. There is a 2nd full bath with direct access to the guestroom and also into the general living area. There is a large screened in porch (360 sq feet) on the main level off the Living Room with a relaxed seating area and dining table with 2 ceiling fans to keep you cool.brbrMost will want to spend your time in the private resort like yard filled with palm trees and tropical foliage. The pool has a waterfall with heater/chiller to allow comfortable temps year-round, has built in barstools and lounging area. The tiki hut has dining for 6 people, is nicely lit for nighttime enjoyment featuring a ceiling fan. Amenities include propane grill, propane smoker, 7.0 chest freezer for bait and ice, and fire pit. Full size 2nd refrigerator is steps away from the pool and dock and outdoor shower (cold only) and large covered filet table for your catch or to crack open a coconut or stone crab claw. You can watch the nature in the deep canal, toss a fishing rod or bring your kayak/boat. The main dock is 30 feet with an auxiliary dock for smaller toys such as a kayak or paddle board. brbrThe house is stocked with most items needed so you can cook and relax including blender, grind and brew coffeemaker, Ninja smoothie maker, vacuum sealer, washer/dryer, AT&T WiFi (1g) that works at the pool and tiki, 3 smart TV's offer streaming in addition to many channels. For those that need to take care of business, we have a basic printer/copier/scanner for minimal use, 27 computer monitor, workspace area with a view of tropical foliage from every window. There are a couple of yoga mats and a small wireless speaker to use inside or outside.brbrThe house has recent renovations including new HVAC, new toilets, ceiling fans,and sliders in the bedrooms and kitchen leading to a wrap around upper level walkway.brbrGreat place to spend all of your time or there are many fantastic restaurants within a few miles (Geiger Key, Sugarloaf Key, Cudjoe Key) such as South of the Seven, Broil, Mangrove Mama's, Square Grouper, The Bent Prop and Geiger Key Fish Camp. Of course, Key West only 20-25 minutes away offers phenomenal activities and fun; Marathon is about a 35 minute drive.brbrSugarloaf Shores is a great place for biking and walking. We are adjacent to an environmentally protected refuge and the jumping bridge is within walking/biking distance. brbrWell behaved dog with minimal shedding considered with $10 additional nightly fee. House stocked with medium sized dog bowls.

Tropical paradise on canal in Lower Keys-pool, tiki, firepit, dock, dog friendly

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$246.04

Amazing canal front 3 bed 3 bath open concept 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 your 80 ft. 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.brbrProperty 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. brbrFeatures include:brBoat ramp (small boats & kayaks)brKayaks (one 2 seater and one 1 seater)brBikesbrDeep freezer (7cubic ft.) great for bait.brHandicap accessiblebrLarge downstairs enclosure perfect for storagebrGreat access to gulf and Atlantic. brNo bridges on boat ride b to gulfbrRV & Motor Coach Storage/Parking AllowedbrLarge yard (8,080 sf)brOpen floor planbrKing Bed in MasterbrHigh speed internetbrCable TVbrLarge outdoor porch off main living areabr3 panel sliding glass door that opens the main living area into open porchbrTile flooring throughout homebr55 Flat Screen TV in Living RoombrSmart TV's w/Wifi and cable in 2 of the Bedrooms brSwim canalbrLadder on seawall to get in and out of swim canalbrFull size washer & dryerbr7 ft. Fish cleaning stationbrDeep/wide/flow-through canal br80 ft. Sea wallbrStep down sea wallbrPeek-a-view views of ocean from upstairs porchbrFisher’s paradisebrNo road noise from hwy 1 (far enough away)brGrillbrCocktail Pool on Seawallbr2 Paddle Boards

Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise

Summerland Key, Florida, United States

Bed

Bath

8

Sleeps

$442.52

Welcome to Fishermans Paradise @ The Pointe on Summerland Key in the Fabulous Florida Keys. Fishermans Paradise @ The Pointe is a beautiful, updated waterfront home with a pool that has all of the amenities you would find in top resorts. The home is located on a flow thru canal with quick and easy access to both the Atlantic and Gulf. The dock can easily accommodate your 45' Center Console with additional space for your boating friends to stop by for a swim after a long day out on the water.brbrThe location and tropical landscaping provides privacy and calmness for your vacation on Summerland Key. Accommodates up to 4 guests with 2 bedrooms and 2 bathrooms. The kitchen includes stainless steel appliances. There are multiple areas for dining: kitchen bar serves as inside dining area, upstairs deck is beautifully appointed with spa located off of the Primary Suite and table for 6, the downstairs dining is located along the canal.brbrThe upstairs deck is equipped with hot tub, dining table, lounge chairs and grill.brbrDownstairs features a resort style, beach entry pool with plenty of seating. The pool has a heater and chiller for year round enjoyment. Located near the pool is an additional grill and refrigeration. A large capacity ice machine is available. There are 2 chest freezers in downstairs storage room for bait and ice storage and an additional refrigerator.brbrThe eat in kitchen is fully equipped and includes a dishwasher, microwave, coffee maker, blender, pots/pans, silverware, etc. brbrSheets, towels, pillows are provided.brbrSmart TV in Living room and Primary SuitebrbrAC - New unit installed 7/1/24brbrSummerland Key is located at MM 24 (half way between Key West and Marathon) Summerland is a quiet neighborhood where you can ride your bike, walk, kayak, fish. Endless activities or you can do nothing at all and just relax beside the pool.brbrThere is a minimum 28 day rental period, no exceptions. County and state taxes are collected (combined at 12.5%) and the renter must be 25 or older.

Fishermans Paradise@The Pointe on Summerland Key 2Bed/2Bath, Pool, 120' of Dock

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$291.92

Newly renovated 2 bedroom, 2.5 bath canal front home with pool in quite, safe neighborhood 25 miles from Key West. House is perfect for couples with 2 king size beds and blackout shades, fully equipped kitchen, front porch with large table, pool, canal front with space for boat, office with computer, wifi, recently renovated. 25 mile drive to Key West and Marathon in different directions. Close to Looe Key Reef and Tarpon Belly Island. Fish cleaning table on seawall. Shed available for storage of fishing and scuba equipment. Enclosure downstairs not included with rental (owner's storage). Minutes to Murray's Food Store and fabulous Square Grouper Restaurant. Newly renovated Key West International is just 30 minutes away. No smoking and no pets allowed. Minimum 28 day rental on Summerland Key

Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water

Summerland Key, Florida, United States

Bed

Bath

5

Sleeps

$676.8

Enjoy one of Florida's most tranquil oceanfront settings. A romantic interlude and tropical adventure where absolutely everything is magnificent. The newly remodeled floor plan is enhanced by a third floor master suite with open water deck. On the main level there is a large tiled porch overlooking the endless horizon. Watch the water birds play as the sun gently sets in the west. The pool area also overlooks the open water and sunset. You may wish to nap or read in the shade of one of the two new thatched Tiki huts also overlooking the water and offshore islands. The home has just been redecorated with new Tommy Bahama, Lexington and Hemingway Collection furnishings. Sleeping arrangements include one king, one queen and two twins. You will find the second and third bedrooms on the second level. This fully-equipped three bedroom, three bath home offers New Big Screen cable TV, VCR, central air and heat, microwave, dishwasher, washer, dryer and a grill. Located on a corner canal and open water on the southernmost point of Summerland Key. Enjoy great boating, diving at Looe Key Marine Sanctuary or the quiet solitude at the pool by the ocean. Just 25 miles to Key West nightlife, dining and attractions, this is truly a Paradise created just for you. This is a non smoking home. Dogs absolutely not allowed. Tenant required to sign a rental agreement with Florida Keys Realty. This home is a 28 day minimum rental per Monroe County Code.

Paradise Views: Oceanfront/Boating

Summerland Key, Florida, United States

Bed

Bath

6

Sleeps

$935.47

Amenities: Dock, Guest Cottage, Pool, Spa, Outdoor Kitchen, Firepit br Kayaks, and Paddle Boards br 30 Minutes to Key West and Marathon br Dog Friendlybr 24/7 Guest SupportbrbrWelcome to Sirena Key, a luxury oceanfront gated estate in the exclusive island community of Summerland Key in the Florida Keys. This private vacation rental is designed for families and groups seeking the perfect blend of resort-style amenities and the comforts of home.brbrStep through the gates and you're greeted by a charming garden with bistro seating, a tranquil spot to relax while children enjoy the open grassy lawn. The estate includes a spacious main house with 4 bedrooms and 3.5 bathrooms, as well as a private guest cottage with a living room, pullout sofa, full kitchen, dining area, bed and bathroom. Together they create the ideal setup for multi-family getaways, offering both elegant gathering spaces and private areas.brbrOutdoors, unwind beside the sparkling pool and spa, complete with hotel-style loungers, a cabana bed, hammock, and umbrellas. A full outdoor kitchen with seating makes alfresco dining effortless, while kayaks and paddleboards invite adventure on the water. Evenings can be spent gathered around the firepit or at the private oceanfront lounge, perched at the edge of the ocean with shaded loungers and breathtaking views.brbrWith space for up to 14 guests, Sirena Key offers the ultimate Florida Keys experience, just 30 minutes from both Key West and Marathon.brbr ️ INDOOR MODERN KITCHEN + DININGbrbr-Chef's kitchen with induction cooktop, stainless steel appliances, and beverage fridgebrbr-Counter seating for 3, and formal dining table for 6brbr-Open-concept living room with large sectional, Smart TV, and motorized blackout blindsbrbr✨ ENTERTAINMENT + LOUNGING SPACESbrbr-Movie theater with projector, oversized sectional, motorized blackout blinds, and pool + ocean views.brbr-Game room with pool table, shuffleboard, Smart TV, motorized blinds, and direct patio access with chic outdoor dining table. brbr-Secret garden entry with lounge seating and dining table. brbr ️ MAIN HOUSE BEDROOMSbrbrAll bedrooms feature the following amenities:brbr✔ Premium beds, pillows, linens, and sheetsbr✔ Ceiling fans br✔ Tv'sbrbr♛ Primary Suite (2nd Floor): King bed, spa-style ensuite, walk-in closet, desk, seating area, Smart TV, water views, coffee nook, motorized blackout blinds. Ensuite includes double vanity, spa tub, dual shower-heads, and private toilet room.brbr-First-Floor Bunk Room: Four twin bunks, sectional, Smart TV, blackout blinds, private porch with dining table for 4, ensuite bathroom with shower and vanity.brbr-First-Floor Queen Bedroom #1: Queen bed, Smart TV, access to Jack-and-Jill bathroom with shower and vanity.brbr-First-Floor Queen Bedroom #2: Queen bed, desk, Smart TV, Jack-and-Jill bathroom access.brbr PRIVATE GUEST COTTAGEbrbrThe separate guest cottage is a fully equipped retreat of its own, perfect for families traveling together or guests who want more privacy.brbr-Studio layout; Queen bed brbr-Living room with pull-out sofabrbr-Kitchen + dining areabrbr-Private bathroom with shower and vanitybrbr BATHROOMSbrbr All full bathrooms are generously stocked with:brbr✔ Shampoo & conditionerbr✔ Body soapbr✔ Fluffy towelsbr✔ Toilet tissuebrbr-Primary Ensuite: Spa tub, dual shower heads, double vanity, motorized blackout blinds, private toilet roombrbr-Bunk Room Ensuite: Shower and vanitybrbr-Jack-and-Jill Bath: Shared by two queen rooms, shower and vanitybrbr-Half Bath: Vanity, sink, toilet, washer/dryer and storagebrbr-Cottage Bathroom: Shower and vanitybrbr RESORT-STYLE OUTDOOR SPACESbrbrSirena Key's outdoor spaces are designed like a private resort.brbr-Automatic front gate for secure entry, expansive driveway with space for multiple vehicles. brbr-Pool and spa with cabana-style bed, hotel-style loungers, umbrellas, and hammockbrbr-Pergola with large sectional lounge sofa brbr-Full outdoor kitchen with seating, Lynx propane grill, Asado grill, and prep spacebrbr-Kayaks and paddleboards available for guest usebrbr-Garden patio and shaded dining areasbrbr OCEANFRONT EXPERIENCESbrbrThis home takes oceanfront living to the next level! brbr-Private dock with fish-cleaning station, running water, and hosebr-Bait fridgebr-Separate oceanfront lounge right with firepit, chairs, and 3 loungers featuring built-in personal shade canopiesbr-Boat lifts are for owner use only and not available to guestsbrbr⚠️ OCEANFRONT SAFETY NOTEbrbrSirena Key is situated directly on the ocean with a private dock and open water access. Due to the home's oceanfront setting and pool design, extra care and supervision are required when children are present. Children must be fully supervised at all times when outdoors or near the pool, dock, or water. Parents or guardians are responsible for ensuring the safety of all members of their party during their stay. This home is best suited for guests who are comfortable managing an oceanfront environment.brbr POINTS OF INTEREST + LOCATION HIGHLIGHTSbrbrSirena Key is located in Summerland Key, one of the most desirable islands in the Florida Keys, just 30 minutes from Key West & Marathon. Guests enjoy easy access to marinas, fishing, snorkeling, and world-class attractions.brbr-Big Pine Key & National Key Deer Refuge – 15 minutesbr-Bahia Honda State Park – 25 minutesbr-Marathon – 35 minutesbr-Key West – 30 minutesbr-Islamorada – 1 hour 15 minutesbr-Key Largo – 2 hoursbrbrEXTRA DETAILS brbr-High-speed WiFi throughout the propertybrbr-Motorized blackout blinds in primary bedroom, primary bathroom, game room, living room, bunk room, and theaterbrbr-Washer and dryerbrbr-EV charger available (requires an adapter for Teslas)brbr-Responsive 24/7 guest support teambrbrBook your stay at Sirena Key and enjoy the ultimate Summerland Key vacation rental. A private Florida Keys estate with luxury amenities, a separate guest cottage, and unforgettable waterfront living.brbrOther Things to Note:brbr-Guests are welcome to use the boat dock during their stay. It can accommodate boats up to 40 ft in length. Please note that boats with more than a 3 ft draft may not be suitable.br-Boat lifts are for owner use only and not available to guestsbrbrHOUSE RULES:brbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrbrAll guests must sign our rental agreement as mandated by Florida Law.brbr-The minimum rental age is 25. A picture ID must be provided to the company no less than 72 hours (about 3 days) before arrival.br-If you would like the pool heated during your stay, there is a $40 fee per day or $1,000 per month. Please coordinate with us prior to your arrival so that we can arrange for the heater to be on.br-Please provide an accurate guest count.br-No smoking or vaping. If evidence is discovered of either smoking or vaping, the guest will be subject to a fine of up to $1,000br-No parties or events. If unauthorized persons are discovered on the premises, guests will be subject to additional fees and/or immediate eviction.br-Quiet time is from 10:00 PM - 8:00 AMbr-This property is equipped with security cameras on the outside of the property at the entrance and pointing at the dock. These cameras are used during the check-in process to verify identity and guest count. If there is an incident, we will review the footage. There are no cameras inside the property or pointing toward the pool area.brbrStarter Supplies:brbrWe provide trash bags, paper towels, toilet paper, detergent, and bathroom amenities to accommodate this home's maximum occupancy for the first three days of your stay.brbrSame-Day Bookings:brSame-day bookings require approval from the company. We will ask you to provide information on your group and the purpose of your stay. If your stay is approved, we require a government-issued ID for identity verification. Your phone number must match the phone number on your account, or we will not be able to honor your reservation. Same-day reservations will not be accepted after 2:00 PM. All same-day reservations require at least 3 hours before check-in. We may have to extend check-in time to later than 4:00 PM.brbrPet Policy:brThis property is dog-friendly, with an additional $750 per month, per pet. For stays of two months or longer, the fee is $2,000 per month, per pet. While staying with us, you are responsible for the actions of your pet. Please keep your dog(s) off the furniture and pick up all waste. All waste should be bagged and disposed of in the outside trash bin. Failure to comply with our pet policy may result in an additional $100 fee. Please let us know if you will be bringing your dog (only dogs under 25 lbs are permitted, sorry).brbrBaby Bundle:brIf you have little ones, we offer: Pack-n-play with a thicker mattress & a high chair for $65 per stay. Please make your request at the time of booking or 24 hrs prior to your arrival.brbrProperty Care Instructions: Treat this home like your own.brbr-Any/all outdoor umbrella(s) must be placed in the closed position when not in use and at the time of check-out. This must be done in order to prevent breakage due to weather conditions. Failure to comply may result in an additional charge.brbr-Please ensure that the grill is covered when not in use. This helps to maintain the grill's condition for future guests. Failure to comply may result in a cleaning or maintenance fee.brbrMid-Stay Cleaning Requirement:brFor all extended stays of 30 nights or longer, a mandatory mid-stay cleaning is required every 30 days.brIf your reservation is 60 days, two mid-stay cleanings will be required, and so on.brThis helps keep the home maintained during longer stays and ensures everything stays in great condition.brMid-Stay Cleaning Fee: $750 (Main House + Cottage)brWe'll reach out after booking to schedule the mid-stay cleaning(s) and send the payment link.

Sirena Key | Luxury Oceanfront Estate, Pool, Guest Cottage, Dock, 30min to Key West

Summerland Key, Florida, United States

5

Bed

4

Bath

14

Sleeps

$203.44

The Sea Shell Cottage UNIT #2 has efficiency kitchen with refrigerator, sink, microwave oven and toaster oven. The main room has a Queen-sized bed, full bathroom with a walk-in shower, table with 2 chairs and a TV. It comfortably sleeps 2 people. The unit is air conditioned and WiFi service is available throughout the resort. Enjoy the communal outdoor pool and covered patio that has a gas grill, griddle and picnic area. There is a laundry room with washers/dryers for our guests to use free of charge.brbrFor those who would like to venture out to the beach, the unit has 2 beach chairs, a beach umbrella, a cooler and beach towels for your convenience. brbrGuest may request to have their pet, 1 dog of 40 pounds or less, accompany them on their vacation and will be required to sign and abide by a pet occupancy agreement as well as pay $75 in additional cleaning fees for the in-depth cleaning required after a dog has stayed in the unit. Guests that bring a dog that has not been pre-approved by management or do not follow resort rules will be asked to leave the resort and all payments will be forfeited.brbrbrACTIVITIES: brbrFishing adventures, bird watching, water sports or some down time relaxing in nature and the beauty of the most desired key in Florida. We’re twenty-five miles to Key West for dinner and nightlike or walk down the block to the local tiki bar, Tonio’s. brbrWe have plenty of space for your boat and trailer. There is a boat ramp just down the block at Tonio's that can handle flat boats 21' or smaller and the boat ramps at Cudjoe Gardens Marina (477 Drost Ave.) and Little Torch Key (SR 4A & County Road) can handle larger boats for a minimal fee.brbrWe’re located twenty-five miles from Key West for dinner and nightlife. Walk 2 minutes down the block to Tonio's Seafood Shack & Tiki Bar. Bahia Honda State Park, with its beautiful beaches, is a 15 minute drive from HIDDEN HAMMOCK RESORT. Our property is not on a waterfront and there are no public beaches in Summerland Key.brbrGuests are provided with the following amenities: a small bottle of dish soap, hand soap and a sponge, a roll of paper towels and toilet paper, a few laundry pods and hotel-size toiletries in the bathroom. This is to help our guests off to a good start. There are grocery and convenience stores in the areas for guests to purchase anything else that they may need.

Cottage

SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!

Summerland Key, Florida, United States

Bed

Bath