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Meet your perfect vacation getaway, Maracaibo Manor! Located on Little Torch Key in the highly desirable Jolly Roger Estates neighborhood, with excellent deep water access for boating, diving, fishing and snorkeling at the famous Looe Key Reef.This roomy home has two bedrooms and two bathrooms upstairs,...
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Bahia Azul, "Bay of Blue" is exactly the perfect spot for your next Florida Keys adventure. The open water views are just stunning and spectacular. Its location at the end of the street makes this a very private get-away.This large home will accommodate all your friends and family with 4...
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Casa Turquesa is the jewel of Summerland Key. Located directly on the beautiful crystal blue keys waters with deep water boat access for the avid angler and plenty of dockage for all the water toys.FLORIDA KEYS VACATION RENTALS! This stylish home is outfitted in Florida tropical style with cool and...
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Located directly on the runway at Summerland Key Cove Airport, this extraordinary 2018 custom-built hangar home delivers the ultimate fusion of aviation lifestyle and refined island luxury in the heart of the Florida Keys.Designed for discerning pilots and luxury tentants alike, this home was engineered...
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Florida Keys Vacation Rentals – Nestled on a pristine canal-front lot, situated in Little Torch Key, this well-appointed home offers all the amenities you will need to enjoy the casual lifestyle of the Lower Keys. The lovely back yard area has a gas BBQ grill, a dining table with seating for six,...
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Key Amenities
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Our Cancellation policy is: Cancellation: If you cancel your reservation in writing 90 days or more before your arrival, you will receive a full refund, less a cancellation fee of $25.00 and Administrative fee. If you cancel less than 90 days before arrival, your payment and any prepaid rent will be...
Featured review
This property is about a half hour north of Key West....perfect for relaxing but close enough to go to town and enjoy the party and any boat trips you might want to take. We would consider renting it again....
Key Amenities
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RARE SINGLE STORY 2500 sq. ft Canal Front Home with gorgeous POOL! Relax in this spacious and serene space with 3 large bedrooms with 3 en-suite baths, plus additional full bath near pool. Kayaks, paddle boards, ping pong, bicycles and pool table! 8 guests only, 6 adults & 2 children. 28 night minimum...
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TWO SEPARATE LIVING SPACES!!! Make your memories at the Aloe House on Cudjoe Key! This home is located on a beautiful crystal clear canal with plenty of dockage for up to a 25 foot boat. The canals here provide great access to some of the best fishing in the Florida Keys. Enjoy boating, fishing or kayaking...
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Welcome to Dockside, your perfect keys getaway! Nestled in a serene location, Dockside offers a fully furnished retreat designed to make enjoying paradise effortless!Dockside is a fully equipped home; featuring a spacious and comfortable living space, a kitchen with all you need to prepare the day’s...
Key Amenities
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This charming 2-bedroom, 2-bath rental home is perfect for your tropical getaway! With a minimum stay of 28 days, it accommodates up to 6 adults and 1 child, making it ideal for families or groups. The master bedroom features a king-size bed, while the guest bedroom offers a queen-size bed. Additional...
Distance to beach: 5 miles to Smathers Beach
Key Amenities
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3 bedroom 2 bath home, heated / chilled pool, plenty of parking for trailers / boats / on a deep water canal with a view to die for. Our home is fully fenced with a large gate opening to enter with your boat trailers etc. (Two king size beds and a full size bunk on the bottom and a twin on top. We...
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This brand new 5/6 bedroom 4 bath oceanfront home has a private pool and will share dock space, kayaks and the gazebo with Blue Palms Retreat home. There is 1 double and 3 single kayaks. Bring your boat- up to 24’ and your snorkel gear. Relax on one of the porches overlooking The Atlantic Ocean...
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This Sugarloaf Key home has it all! The views, the pool, the boating and the privacy, and oh, did we mention the views?Located at the end of a quiet street, this property is gated, and both waterfront and canal front. There is a large heated pool dockside, with lots of space to soak up the sun and...
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Welcome to a luxury “Reel Escape” in the Lower Florida Keys! Located on Summerland Key in the highly desirable Summerland Cove neighborhood, this four-bedroom, two-bathroom home has plenty of space for everyone to relax in comfort.The interior is spacious, with three bedrooms on the first...
Key Amenities
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Serenity found in the Florida Keys! This home is situated on a beautiful canal in the Jolly Roger Estates of Little Torch Key. There is plenty of room for your boat with access to the best boating, fishing, diving, and snorkeling in the lower Keys.The exterior of this home boasts a large concrete...
Distance to beach: 7 miles to Bahia Honda State Park
Key Amenities
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This newly remodeled home is cozy, yet spacious.This open concept, single family home is located on a canal and just a few seconds from the ocean. Fully furnished with Keys-inspired touches, this home comfortably sleeps 6 people with 3 bedrooms and 2 bathrooms.Spend the day at Bahia Honda State...
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The Conch House is a very special little piece of paradise located at mile marker 28.5 on Little Torch Key. You can dock your boat right in your own front yard!! It sits on the open water on Pine Channel on the Gulf side of the Keys. The newly constructed cement L shaped dock can accommodate up to a 32’...
Featured review
House was great, nice layout, pool and view. We had a wonderful time. I would have liked a dock to fish in deeper water from, more reeks and grass beds here. Beautiful though, great host
Key Amenities
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Welcome to Margarita Manor – Your Tropical Escape in the Florida Keys!Set your watch to island time and relax at Margarita Manor, a vibrant waterfront oasis perfectly suited for sun-chasers and boating enthusiasts alike. Located just moments from open Atlantic waters, this breezy retreat offers...
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This pet-friendly home completed in 2012 has 5 rooms, 3 king-size beds, and 4 twins plus a twin sofa bed and three full bathrooms. The home has a huge kitchen with custom made wood cabinets and top of the line stainless steel appliances including an indoor gas grill and a standing freezer: to keep the...
Featured review
SIX STARS * * * * * *This is a wonderful home with channel access right behind the house. It's perfect for the whole family, very spacious. The owners are very accommodating, making sure everything...
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Welcome to “Casa Solimar,” house of the sun and sea! When you arrive at this home you will see that the name suits it…situated canal front and just a few homes in from open water, with a heated pool and spa! The lower-level boasts an updated additional living area for family and friends,...
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This 3 bedroom/2.5 bath home is located in a quiet neighborhood on a deep canal with easy boating access to open water.The Master has a King bed, 2nd bedroom has a Queen. There is an extra sleeping area with a queen and twin bunk bed, 1/2 bath and outdoor enclosed shower. 2 beach bikes and 1 double...
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Start your vacation in the Keys off right at Blackbeard’s Escape! This unique home has it all. Main living area on first floors is a 2-bedroom 1 bathroom home with gourmet kitchen, lovely finishes and details plus comfy king size beds. Cooling is great with mini ac splits and large flat screen tv’s...
Featured review
Our family throughly enjoyed our stay at this house. It was very clean and there was plenty of room. It was perfect for the fishing families. Plenty of dock space, a bait freezer, and an ice machine. We...
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Aaarrrghhhhhhh MATEY! Florida Keys Vacation Rentals – Looking for a perfect sunny get away in the beautiful Florida Keys? Blackbeard’s Bounty is just the place for you and your guests!This tropical oasis is located on Little Torch Key and is only 28 miles from Key West. Situated on a wide...
Distance to beach: 3 miles to Bahia Honda Park
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Modern 4 bedroom 2 bath stilt home centrally located in Big Pine. Heated salt water swimming pool. Corner canal front lot with 120 ft of dockage. 5 min. to the Gulf and 10 min. to the Atlantic. Close to the Winn Dixie grocery store. Free public boat ramp 5 min away. Room on property to park 6+ cars...
Featured review
Well, we think the house is very nice and clean. Great location, lovely neighbors nice quiet place we have only positive things to say and nothing negative so have a great day
Key Amenities
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Tropical Oasis on the Canal: Tiki Bar, Heated Pool & Outdoor Grills Big Pine Key, FL | 5 BR, 3 BA | 28-Day Minimum Stay Escape to the ultimate Florida Keys retreat! This expansive, fully fenced canal-front estate offers a resort-style experience designed for families and groups seeking privacy,...
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The name says it all, find your dream vacation home at Million Dollar View! Located on Big Pine Key, this perfectly placed piece of paradise sits on a convenient corner lot, providing ample space for boats, and some of the fastest access to water you can get anywhere in the Keys! When you aren’t...
Distance to beach: 10 miles to Bahia Honda
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Welcome to Paradise Palms! This amazing 3 bedroom home on Cudjoe Key is perfect for your next Florida Keys vacation! Tropical landscaping surrounds an inground pool that overlooks a beautiful canal...everything you could want and more! There is also large concrete dock for your boat, quick easy ocean...
Featured review
My family and I stayed for the month of June 2022 and this was the first time we had visited Cudjoe Key. The house was beautiful and VERY clean. The kitchen was well equipped with everything you needed...
Key Amenities
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What a great sunset view from this house! Fun in the sun surrounds this spot right on a wide canal with excellent access to fishing either the Gulf or the Atlantic side. Any outdoor enthusiast would be content here as the boating, diving, snorkeling, or kayaking is right out your back door.After a...
Featured review
This house has just about every and anything you could need. Very quiet and nice area. Owners went out of their way to ensure our stay was as stress free as possible! We had a 19’ boat docked at the canal...
Key Amenities
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Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. This house includes all the elements you need for an amazing vacation. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24'...
Featured review
The location was exactly what I had hoped. It was secluded, but close to everything. The water views were worth every penny!
Key Amenities
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Welcome to San Remo Retreat, a very unique property located in the highly desirable Doctor’s Arm neighborhood on Big Pine Key. Bring your boat, plenty of dock space here! The fish cleaning table will hold your biggest catch of the day!You will feel right at home in this very nicely decorated,...
Featured review
This house is spacious and fully equipped for a fun and adventurous vacation. There was ample dockage for our boat and the bait freezer, ice maker and storage were an added convenience. We enjoyed our vacation...
Key Amenities
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You will be pleasantly surprised when you arrive at Grouper Therapy on Little Torch Key. One of the few ground level vacation homes. No steps here!!Nicely styled kitchen with granite counters and newer appliances and a small breakfast bar to enjoy morning coffee and snacks.The living area is roomy...
Key Amenities
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Blue Tranquility will be the perfect destination to get some rest and relaxation for your next Florida Keys vacation. Located directly on the ocean side of South Pine channel, which offers wonderful sunrises and moon rises. Kick back and enjoy the balmy breezes on the serene screened in porch. The pool...
Key Amenities
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Welcome to your ideal vacation getaway in the heart of the Florida Keys! Located in the serene Cudjoe Key, this charming home offers luxurious amenities and a perfect blend of comfort and style. Imagine waking up in a cozy, beautifully decorated home and enjoying your coffee on a private deck surrounded...
Featured review
This was the best vacation I have ever had in Florida. The house was beautiful and it was very peaceful sitting out on the canal. Only 20 miles to Key West makes for easy day trips. We went 5 times! The...
Key Amenities
About this property
This Lower Keys 6BR/4.5 getaway has a private boat basin and ramp, a pool, and a separate guest house with its own kitchen and living room. Relax in your outdoor oasis at the water's edge before heading out to scuba dive, shop, fish, or even embark on a lobstering adventure.Located on Pine Channel,...
Featured review
We have stayed here several times in the past and we had another amazing stay. The house is very spacious.
Most Lower Keys vacation rentals require a 28-night minimum stay under Monroe County rules, although a few gated communities and specially permitted properties allow shorter stays. Rates below include a 12.5% combined tax, plus cleaning fees and other charges. You pay no booking fee when you book directly with the owner. Owners set their own cancellation policies, so review the terms before booking.
SHORT STAY
3 nights
all in
$575/night
| $511 × 3 nights | $1,533 |
| Cleaning + damage waiver | $0 |
| Tax (12.5%) | $192 |
| Booking fee | $0 |
| Total | $1,725 |
WEEKLY STAY
7 nights
all in
$556/night
| $494 × 7 nights | $3,458 |
| Cleaning + damage waiver | $0 |
| Tax (12.5%) | $432 |
| Booking fee | $0 |
| Total | $3,890 |
MONTHLY STAY
30 nights
all in
$487/night
| $433 × 30 nights | $12,990 |
| Cleaning + damage waiver | $0 |
| Tax (12.5%) | $1,624 |
| Booking fee | $0 |
| Total | $14,614 |
The best time for a Lower Keys stay is March through May, when visitors are drawn to warming water, spring fishing tournaments, and the peak of Key deer fawning season in May. Summer brings lobster season and the Lower Keys Chamber Dolphin Tournament at Kiki's Sandbar. Storm activity is heaviest fr
| Month | Median nightly | Difference from annual | High / low air temp | Water temp | What’s going on |
|---|---|---|---|---|---|
| January | $283 | 0% | 60° / 37° | 63° | 30A Songwriters Festival |
| February | $293 | +4% | 64° / 40° | 62° | Seaside School Half Marathon; wine festival at Alys Beach |
| March | $293 | +4% | 70° / 46° | 65° | Spring break crowds build |
| April | $283 | 0% | 76° / 52° | 70° | Sandestin Wine Festival; Seabreeze Jazz Festival |
| May | $267 | -6% | 83° / 61° | 77° | Digital Graffiti at Alys Beach; ArtsQuest Fine Arts Festival |
| June | $267 | -6% | 88° / 69° | 83° | Sea turtle nesting, beachfront lights down |
| July | $283 | 0% | 90° / 72° | 85° | Fourth of July events across 30A |
| August | $283 | 0% | 89° / 71° | 86° | Warmest water water of the year |
| September | $267 | -6% | 87° / 67° | 83° | Destin Seafood Festival; Red, White & Blues concert, Alys Beach |
| October | $267 | -6% | 80° / 55° | 79° | Harvest Wine & Food Festival, WaterColor; Halloweener Derby, Seaside |
| November | $267 | -6% | 71° / 46° | 72° | Thanksgiving 10K, Rosemary Beach; Mountainfilm on Tour, WaterColor |
| December | $283 | 0% | 62° / 40° | 67° | New Year's Eve fireworks |
Based on the median nightly rate on FloridaRentals.com.
A few practical details can shape your stay. Consider airport distance, wildlife protections, reef rules, and beach access before choosing your rental.
Key West International (EYW) is about 25 minutes from Sugarloaf Key and 40 minutes from Big Pine Key. Miami International Airport (MIA) offers more flight options but is about 2 hours and 40 minutes from Big Pine Key with tolls.
Key deer are endangered and protected. Don’t feed, touch, or harass them. Feeding them can spread parasites and disease through the herd. Also be careful driving and obey posted speed limits on US-1 through Big Pine Key, especially after dark.
Don’t fish, collect marine life, touch coral, or stand on the reef in the protected area. If you take a boat out to the reef, use designated mooring buoys where available and never anchor on coral.
Bahia Honda can close when its day-use areas reach capacity. Check park conditions before you leave and arrive early on weekends and holidays. The boat-trailer lot can also fill up, limiting launch access.
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