Vacation Rentals By Owner In Summerland Key, FL

Ocean Breeze is the largest of our 5 cottages at 1500 square feet. It's perfect for your family vacation, sleeping 7 people comfortably, with two full bedrooms (one with a queen bed and the other with two queen beds) and a pull-out sofa as well as two full bathrooms. It comes complete with a full kitchen, large living room with fireplace and dining room as well as a screened-in front porch for outdoor dining. The rear of the house has a game room with a full size pool table and an outdoor patio with barbeque and picnic table. 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, which are all just steps away from the Ocean Breeze Cottage. We have a laundry room with washers and dryers that are free of charge.brbrFor those who would like to venture out to the beach, the unit has 4 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 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.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 nightlife 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

Ocean Breeze House - Sleeps 8 - ESCAPE THE COLD; OUR POOL IS HEATED!

Summerland Key, Florida, United States

Bed

Bath

8

Sleeps

$1072.77

Your cozy getaway awaits in Summerland Key at this wonderful estate. With seven spacious bedrooms, including four king beds and three twin beds, guests have plenty of room to relax. Six bathrooms feature jetted bathtubs and showers, offering a touch of luxury throughout the home. Stay comfortable with air conditioning and keep up with your routine in the fitness room. Whether you’re gathering with family or friends, this excellent estate provides a perfect setting for memorable moments. It’s easy to see why you’ll be able to unwind at our place. 3 Tiered pool area, Hot Tub, Dive Pool, Lazy River

Spacious 7-bedroom estate with AC in peaceful Summerland Key

Summerland Key, Florida, United States

7

Bed

Bath

16

Sleeps

$270.75

The Palm Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently renovated. The main room includes a Queen sized bed, TV, table with 4 chairs, a full kitchen, full bath with a walk-in shower. The front room has a trundle bed with two twin mattress and a TV. There is a laundry room on the property for our guests to use that is free of charge. brbrIt can comfortably sleep 3 people. Just outside the front door is an outdoor table and chairs. 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. 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 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.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

PALM COTTAGE - Sleeps 4 summer fun ..lobster season.

Summerland Key, Florida, United States

1

Bed

1

Bath

4

Sleeps

$297.03

Experience the ultimate tropical getaway at BananaCabana, our vacation rental home located in the heart of the lower Florida Keys. Nestled on scenic Sugarloaf Key, just minutes from the sparkling waters of the Atlantic ocean or the Gulf of Mexico, dockage for two boats. Our property offers the perfect blend of comfort and convenience for your next vacation. Immerse yourself in the laid-back island lifestyle and create lasting memories with family and friends. A tropical paradise with over 1/3 acre of lush landscaping, featuring generous living space and privacy in the Lower Florida Keys at Mile Marker 17. This charming stilted waterfront home was beautifully updated in 2023 and decorated in a whimsical and colorful Keys style.brThe open plan kitchen, living, and dining area is the perfect place to relax after a day on the water or sightseeing in Key West. Enjoy a frozen drink while you surf the wireless internet, watch the flat screen TV with cable, or punch in your Netflix code and view all your favorite TV shows and movies.brThe large living room and comfortable sofa is a big hit with the kids! The kitchen is perfectly equipped to prepare your favorite meals. For dining out, there are many fantastic restaurants nearby – just check out our 'menu library.' The living/dining area opens onto a covered porch with Weber gas grill, dining table and relaxed seating. Tranquil breezes and lovely canal views await you. Tired after a long day on the water or sightseeing in Key West The master suite has a king-size pillow top mattress, flat-screen TV with cable, and a lovely updated en suite bathroom. The guest room has a king-size bed with pillow top mattress and plenty of closet space. The guest bath is also newly renovated with new tile, fixtures and granite counter top. With so much to see and do in the Lower Keys you will appreciate coming back to the serenity and privacy the Banana Cabana has to offer.

2-bedroom bungalow in charming Sugarloaf Key with dock, close to Key West

Summerland Key, Florida, United States

Bed

Bath

4

Sleeps

$558.87

Gorgeous open water 3 bedroom 2 bath pool home on Summerland Key! This completely remodeled home features an open floor plan with stunning views of the Atlantic from almost every window. The fully equipped kitchen is great for entertaining with island seating for 4 and dining area with seating for 8, the whole family will be comfortable! The 3 bedrooms feature a king bed in the Master as well as in the guest bedroom and a bunk bed with queen & twin sized mattresses. Outside there is protected deep water dockage for all of the water toys as well as a heated pool with plenty of decking and beach area for the sun bathers! If you are looking for a great getaway in the Keys this property has it all!! You will not be disappointed!!

Gorgeous 3 Bedroom 2 Bath Open Water Pool Home on Summerland Key

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$336.8

Beautiful Waterfront Getaway on Cudjoe Key Escape to this serene 3-bedroom, 2-bath waterfront vacation rental on picturesque Cudjoe Key, FL. Thoughtfully designed for relaxation, this home offers everything you need for a comfortable and memorable stay. Newly Remodeled Kitchen: Cook up delicious meals in the modern, fully updated kitchen featuring new appliances, stylish countertops, and ample space for preparing island-inspired dishes. Enclosed Sunroom: Unwind in the sunroom with views of the open water. With 2 sets of sliding glass doors, it's the perfect spot to enjoy refreshing winter breezes. Spacious Living Area: Relax in the cozy living space, perfect for lounging after a day of exploring the Florida Keys. The entire home has been recently remodeled with modern updates and tasteful decor for your comfort. Waterfront Charm: The property features a 20 foot dock with stunning water views. Enjoy your morning coffee or an evening cocktail as you take in the tranquil scenery. Whether you're planning a quiet retreat or an adventure-filled vacation, this beautifully updated Cudjoe Key home will be your ideal base for exploring the nearby attractions and soaking up the tropical vibes!

Newly Remodeled Beautiful 3 Bedroom 2 Bath Canal Front Home

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$614.73

Welcome to the Prestigious neighborhood of Summerland Key Isles!! This gorgeous 3 bedroom 3 bath property has one of the largest swimming pools in the Lower Keys!! Plenty of room to lay in the sun or relax in the shade in the huge screen porch overlooking the beautiful Florida Keys waters taking in gorgeous sunsets. This fully equipped house features 2 bedrooms on the upper floor with King size beds in both bedrooms. The downstairs bedroom features 2 twin beds and a queen bed. Fully equipped kitchen perfect for entertaining. Great boating with quick access to the Gulf or the Atlantic and world class fishing and diving. Come check out this stunning property!

Beautiful 3 Bedroom 3 Bath Open Water Pool Home With Excellent Boating

Summerland Key, Florida, United States

Bed

Bath

8

Sleeps

$621.08

Make some memories at this unique and family-friendly place. Beautiful, custom designed concrete waterfront pool home with open water views and quick boating access.brbrSplit-floor plan with master suite off the family room with:br- Open water viewsbr- Outside Deck and Pool areabr- 2nd level Guest Bedroombr- Large Master Bedroombr- Large Guest bathroombr- Remodeled Kitchen with Granite countersbr- Stainless steel appliancesbr- Dining Room with Islandbr- 30 Minutes from Key West

Villa

Beautiful Oceanfront Villa with Pool and near Key West, Florida

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$171.73

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbr***We consider discounts for multiple month rentals*** brbr brbrWelcome to The Hideaway, a charming canal-front retreat nestled adjacent to a serene nature preserve on Big Torch Key! brbr brbrTucked away in a tranquil neighborhood off the beaten path, this haven is tailor-made for those seeking a harmonious blend of nature, solitude, and quintessential Keys living. Unwind in seclusion as you dock your boat along the sea wall, granting you unparalleled water access to both the Gulf and Atlantic, mere minutes away. Embrace the simplicity of classic Keys living while relishing the melody of gentle waves lapping against the shore. Awaken your senses on the porch, where your morning coffee and evening cocktails become a part of the vibrant ecosystem that envelops you. Immerse yourself in nature's serenity as you sip, relax, and let the world fade away. While The Hideaway offers a tranquil escape, the vibrant Keys offer their own allure. With just a 40-minute drive to Key West and 25 minutes to Marathon, you're perfectly positioned to explore the myriad treasures this unique archipelago has to offer. Seize the opportunity to make The Hideaway your own private sanctuary, where nature, solitude, and timeless Keys living seamlessly converge. brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1: Queen Bed, Smart TV with Roku (no cable/satellite TV) brbr brbrBedroom 2: Queen Bed, Smart TV with Roku (no cable/satellite TV) brbr brbrLiving Room: Sofa with Pull Out Queen Bed, Smart TV with Roku (no cable/satellite TV) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal, no dishwasher) brbr brbrAMENITIES: brbr brbr- 25' of dockage (boat lift will have a boat on it and not available for guest use) brbr brbr- Fish Cleaning Station brbr brbr- Bait Freezer brbr brbr- Screened Porch brbr brbr- Outdoor Seating brbr brbr- Tandem Kayak brbr brbr- Ping Pong Table brbr brbr- Charcoal BBQ Grill brbr brbr- Parking for a maximum of 4 vehicles, including boat trailers. Recreational Vehicles may not be parked on the property. Owner's boat trailer will be stored on property. brbr brbr- Linen's and towels provided brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrNo 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 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 Hideaway: Lose Yourself At This Recently Decorated Canal Front Home on Big Torch Key, Dockage!

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$271.86

Home has to be rented for 28 days or longer city rule. Home has high vaulted ceiling and 30 feet of sliding glass windows which over looks the canal, lagoon and ocean. On quiet dead end street in a great neighborhood this 2 bedroom home with a loft. Centrally located about 25 minutes to Key West or Marathon. Private backyard has pool and lots of shade to relax. We fish, paddle board and kayak off the dock. easy access to ocean and gulf. Trying to rent January and February together will rent separate starting on April 31, 2026.

Beautiful Lagoon view on canal pool home Summerland

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$316.46

brDrive In, Fly In. Boat Out. Live Elevated.br Welcome to a truly rare gem nestled between Marathon and Key West—a solid concrete, hurricane-proof home built for luxury, comfort, and adventure. Designed with both pilots and boaters in mind, sunseekers too, this unique residence sits directly on a 2,500-foot private airstrip, allowing you to taxi your small aircraft right into the airplane hangar beneath your home.br Step upstairs and you’ll find elegance at every turn—11f' high celling's from tile floors and granite countertops to spa-quality tile bathrooms and high-end appliances. Large Smart TV with surround sound .The screened-in porches offer the perfect spot to unwind, enjoying ocean breezes without the bugs. And with high-speed WiFi, you’re never far from the world—unless you want to be.br Out back, a Built in pool and Tiki Bar also a 65-foot wide canal with a 40 ft slip that connects you straight to the open ocean—just a 10-minute boat ride away. Whether you’re flying in, driving in, heading out by sea, or simply soaking in the serene views, this home is a private paradise made for those who live life a little higher, and a little bolder. feel the KEYS with the beautiful topical landscaping.br Perfect for aviators, anglers, or anyone seeking a one-of-a-kind Keys lifestyle.

Summerland Airport Hangar Home with Pool, Private Runway and deep wide Canal

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$138.88

Only 10 minutes to bahia honda beach, rated top ten every year. 35 min to key west. 3 hrs to miami, a great sight seeing attraction with the 7 mile bridge, and many more. 25 minutes to marathon. 5 or 6 restaurants in the local area.

Mobile Home

20 ft from your room to a clean canal full of fish and lobsters and crabs.

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$216.05

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