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Welcome to the Key House, a completely charming, canal front home located in the ultra popular Jolly Roger Estates on Little Torch Key.A cute tropical them from the outside in, you know you are in the Florida Keys! The exterior boasts an immaculately kept grounds with ample storage for your gear,...
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Sea Magic on Marlin – Panoramic Open Water Views & Spacious5-bedroom HouseYour Sugarloaf Key adventure begins at this beautifully located waterfront home. Panoramic water views and access allows for boating, swimming, kayaking, snorkeling, and fishing and this 5-bedroom house welcomes...
Key Amenities
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Beautiful house in Big Pine Key, Fl on the water. Bring your boat and have it in the water in the back of the house. Comes with everything needed for your amazing stay. There is an ice maker for your use as well. Also you are only 30 miles away from the world famous Key West.
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Access the ocean or bayside via boat from your front porch in Ramrod Key. Property is located at mile marker 27.5, minutes from grocery and drug stores on Big Pine Key, and about a half hour to Key West or Marathon. Updated 2 bedroom, 2 bathroom home offers stunning open water views and sunrises. Inside...
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Amazing Waterfront Home with Fabulous Pool and Sunset ViewsWelcome to the Sugarloaf Guest House, the perfect Florida Keys Island Getaway. As you enter the gate to this charming seaside cottage, you will experience its charm and relaxing vibes. A gorgeous new pool with graceful waterfalls make it the...
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Key Amenities
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Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open from Aug.6th to April 1st. This is a spacious oceanfront home with breathtaking open water views! It is located on beautiful Ramrod Key 85 ft concrete seawall facing the priceless Atlantic ocean teaming...
Featured review
This 4 bedroom, 2 bath is more than a house, it feels like home! From the fully stocked kitchen to the various board games available, this house will keep you busy. You can also rest here as the nights...
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BOAT RENTAL: We offer to rent our personal boats to our guests, only. We own: Flats Boat - 17 ft Ranger with E Tech 75 Bay Boat - 24 ft Bay Scout with 225 HP Yamaha Open Fisherman - 29-ft Ocean Runner with 2025 twin 250 HP Honda's. These boats are set up with everything you need to fish the Keys,...
Featured review
I really cannot say enough good things about this home nor about the hosts. Mr. John was Johnny on the spot from the moment that we arrived. He was at the property when we arrived and happy to show us the...
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Florida Keys Vacation Rentals – 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...
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“Endless Paradise” is truly a Cudjoe Gardens gem! This ground level (no stairs here!) vacation rental home is walk in and relax ready! Located in the highly desired Cudjoe Gardens neighborhood known for its great boating access, ground level prestigious builds, local marina and don’t...
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We would like to invite you to stay at our peaceful keys getaway. Enjoy the spacious porch overlooking the pool and canal, this is great for my wife and I to watch our kids while they are swimming and fishing off the sea wall. As you can tell by the pictures you can catch hugh snapper right off the sea...
Featured review
My son and brother and myself have been staying at Lee &Tracey’s house on cudjoe key in late summer for years and haven’t missed a year yet we all ways have a wonderful time there fishing and diving...
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Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best deep water boating in the Lower Keys!Decorated in fine island-style this private home is definitely a 5-star property. Tile floors, open and airy kitchen, living and dining area...
Featured review
Not my first time with action keys, always had good result with everyone at this company! Wish they would rework there utilities policy , it’s hard enough to pay rent for a month.
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Welcome to Blue Wahoo, the perfect Florida Keys Island Getaway.Check-in to this gorgeous coastal home for a wonderful vacation on what is arguably the nicest of Florida’s lower keys. This house has it all. It is beautifully furnished; from a well-equipped kitchen and updated living room to...
Distance to beach: 4 miles to Bahia Honda State Park
Key Amenities
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Beautiful waterfront home located in quiet Eden Pines neighborhood. Easy access to Pine Channel to fish, dive, and explore the Atlantic Ocean, the Gulf of America, or the backcountry. 60 feet of seawall with a set of davits, boat lift, and a tiki hut. Public boat ramp one block away. No neighbors across...
Featured review
We have stayed at alot of vacation homes in the keys over the course of the last 7years and this one is by far our favorite! Richard was an amazing host, he always made himself available for a text, email...
Key Amenities
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Last minute discount, 28 day minimum, 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...
Distance to beach: 23 miles to Marathon
Key Amenities
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Charming house on a canal with all amenities like home. Bring your own boat and park it on the dock for the duration of your vacation. Convenient located 25 miles before Key West. Nice restaurants and groceries shopping 10 minutes from the house Marathon is only 30 minutes away. A short boat ride...
Featured review
After a several weeks stay on Little Torch Key, we are comfortable with these obserservations, cozy, clean, comfortable, and quiet. Just what we needed after traveling since mid-November. Easy access to...
Key Amenities
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Family House in Big Pine Key, Fl on the water. Bring your Boat and have easy access to the most beautiful waters of the Keys. Boat dock on the back of the house, and house comes with everything, it will make you feel at home.Welcome to your Ultimate Luxury Island Escape! This beautiful waterfront...
Featured review
This was our 2nd year staying at the Cloud 9 House home...if we could we'd stay a month instead of 10 nights the first year and 14 this year! The house has everything you could want and the hostess is amazing...
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The Shores of Sugarloaf Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and SunsetsWelcome to the Shores of Sugarloaf, the perfect Florida Keys Island Getaway. Check-in to this gorgeous coastal home and enjoy a lovely vacation on one of the Florida Keys most desirable keys-Sugarloaf. This house...
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Welcome to the home with one of the best sunset views on Big Pine Key! This is a great location, with awesome views, and super quick boating access to both the Gulf and the Ocean. This three bedroom, three bathroom home is setup perfectly for the avid fisherman, boater, paddleboarder, or just the relaxed...
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Welcome to Oceanview Oasis, a most spectacular open water home on Summerland Key. This is a completely remodeled, state of the art, waterfront retreat with new oceanside pool, adjacent spa and screened porches on two levels for outstanding views at every turn.Interior living space offers a split floor...
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Welcome to Your Canal-Front Keys RetreatTucked away on Big Pine Key, this elevated canal-front home offers the relaxed rhythm of the Florida Keys with room to breathe, unwind, and reconnect with nature. From peaceful mornings on the deck to spectacular sunsets over the water, this home is designed...
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Welcome to our 5 bedroom with optional 6th bedroom home, “Reel’em Inn” Big Pine Key, an excellent location for a relaxing vacation with family and friends 31 miles from Key West’s Mile Marker 0. This spacious 5-bedroom home is on a double lot with plenty of parking and 150 feet...
Featured review
We've stayed in this home for a month for 3 years, 2025 being our 4th year we added a month. We stayed in the home before Jeff and Christine bought it and loved it then. They've made so many improvements...
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Come enjoy this newly listed property on Beautiful Ramord Key house with a southern view of Newfound Harbor and the Atlantic !! House has a 60 ft+ dock for your water toys. Enjoy lobster season, fishing (back water and deep sea great snorkeling and dining all minutes away. Ramrod is easy boating...
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Sunrise Drive, the perfect 3 bedroom, 3 bath home for your stay in the Keys. It’s located in Tropical Estates, a quiet upper scale community with water access throughout. A perfect location if you are looking for a tranquil island setting but close to the fun as Key West is just 25 miles south....
Featured review
I was lucky enough to stay here December and part of January! EXCELLENT owners. AWESOME pool area and a WONDERFUL comfortable home!!! Has everything you need and then some! It is close to Key West and...
Distance to beach: 15 miles to Bahia Honda
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This luxurious home overlooking Cudjoe Bay on the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with 11 total homes. This is #109 and I also rent 111 and 107 in case you need more than one. We are 90 feet from the water's edge facing Southwest. Lounge...
Featured review
Great location, views were gorgeous from our waterfront decks, 30 mins. to airport! Rental was clean, comfortable & well equipped with everything you need & then some. Home owners thought of everything...
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Beautifully updated for your stay. This is not your typical vacation rental home, everything is new and curated for a wonderful stay. Conveniently located on deep water for Gulf or Atlantic access, no low bridges to navigate, with a natural preserve across the canal for privacy. Get ready to relax in...
Featured review
We absolutely loved our stay! The house was so cozy, clean, bright, and peaceful, and it had everything we needed to feel right at home. One of our favorite parts was enjoying our morning coffee on the...
Key Amenities
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The 3 bed/3 bath canal front home provides quick access to the Atlantic and Looe Key with no bridges.60' of canal front with 40' of seawall and a cleaning station.After a day on the water, enjoy the refreshing outdoor shower or soak in the large master bath tub.The screened patio...
Featured review
We really enjoyed our stay in this well appointed home. The location is an old Florida Keys experience. Great neighborhood with no thru traffic, friendly neighbors and great sunsets. The reef is a short...
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Beautiful , home on deep water canal in desirable Breezeswept Estates is your private resort for a minimum of 28 days . Heated, saltwater pool adjoins huge ground level great-room with living area, dining area, shower , gas grill, pingpong table and so much more contained in private setting ! 40 ft dock...
Featured review
Very nice pool & dock area. Neighbors very friendly. Downstairs area very nice for socializing near pool area. House was comfy for family with adults & children. A great location for restaurants...
Distance to beach: 15 miles to Bahia Honda
Key Amenities
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This luxurious home overlooking Cudjoe Bay on the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with 11 total homes. This is #111 and I also rent 109 and 107 in case you need more than one. We are 40 feet from the water's edge facing Southwest. Lounge...
Featured review
Well kept clean condo and good host. The host has a nice binder with information and local things to do with mile markers. I would have liked to have the list emailed to me before we came to plan more...
Key Amenities
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Discover your own private escape with this beautiful canal-front home, perfectly positioned for those who love nature, boating, and peaceful coastal living. Backcountry & Ocean Access Enjoy direct canal access leading to incredible backcountry waters ideal for kayaking, paddleboarding, and world-class...
Distance to beach: 15 miles to Bahia Honda
Key Amenities
About this property
This luxurious home overlooking Cudjoe Bay on the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with 11 total homes. This is #107 and I also rent 109 and 111 in case you need more than one. We are 140 feet from the water's edge facing Southwest. Lounge...
Featured review
Susan & Jennifer are great to deal with, this was our 3rd trip to the property, and we can't wait to go back!!
Distance to beach: 10 miles to Bahia Honda
Key Amenities
About this property
Paradise awaits in the Lower Keys! Situated on a large corner lot, you have over 200 feet of concrete dockage so BIG BOATS are welcome! Featured on " American Dream Home," this vacation home will not disappoint. Whether you're looking to fish the Atlantic or Gulf, snorkel at Looe Key Reef,...
Featured review
This home was absolutely beautiful! My husband and I, along with his family, stayed here and it accommodated 6 adults, 1 teen, a baby, and even our dog—everyone was perfectly comfortable. We loved relaxing...
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Looking for a home away from home? Via Villa is the place! This vacation home is located in Cudjoe Gardens on Cudjoe Key, only 20 miles from Key West. Situated on a corner canal, there is ample dockage for large boats, water and electric on the dock, as well as a waterside fish cleaning table. Via Villa...
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Escape to the Florida Keys and experience waterfront living at its finest in this beautifully renovated 5-bedroom, 3-bath vacation home located in desirable Cudjoe Gardens, just 17 miles from Key West and minutes from world-class boating, fishing, diving, and snorkeling.This spacious 3,500-square-foot...
Featured review
I began visiting this property in ~1998 and get back there as often as I can.It is a wonderful house, beautifully decorated, with convenient deep water access to the best fishing/fly-fishing (minutes...
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INGROUND HEATED AND CHILLED POOL TO COME IN NOVEMBER!! Daydreamin’ blue in the super-desirable Summerland Cove neighborhood! There is plenty of room for family and friends here, with four bedrooms and a huge open concept kitchen and living room, you won’t ever feel crowded. Additionally, a...
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Summerland Cottage-Relax At Our Little Piece of Paradise!Host Missy Proctor Phone meeting is required before booking approval. Please email me for my number and any questions you may have :)Come and Enjoy our Cozy Little , Nostalgic Keys Stilt Cottage on Summerland Key! Enjoy Open water views...
Featured review
We are a family of three with a 16-year-old son. We rented on the adjacent Cudjoe Key for the last 15 years. We focus on fishing, snorkeling, and exploring the area by boat. This year, our usual rental...
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House - 2 Bedrooms, 2 Bathrooms, Sleeps 4. Come enjoy our hidden retreat in upscale Cudjoe Gardens. This home is conveniently located only blocks away from Cudjoe Gardens Marina. This single level home is situated on a crystal clear flow through deep water canal. The home features an in ground private...
Featured review
We absolutely loved this home! We've been traveling to the Keys for 15 years and this is one of our favorites. A quiet neighborhood which is fantastic. Fred is excellent with communication.
Key Amenities
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This super cozy, comfortable 2-bedroom, 2-bath vacation rental is located in the heart of Cudjoe Key, just minutes from the open ocean. Perfect for fishing, snorkeling, and diving enthusiasts, the home boasts easy access to some of the best spots in the Florida Keys.Relax and unwind in style after...
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Summer never ends in the Florida Keys! Endless Summer is located on Summerland Key in the very desirable Summerland Cove neighborhood. This is a two bedroom, two bathroom comfortable home with additional and very accommodating living space on the lower level.Upstairs is open concept living with a...
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A Little Torch, Jolly Roger Estates unique find! Two separate living spaces for the price of one! Located in one of the most desirable neighborhoods in the Lower Florida Keys, this canal front home is truly a vacation rental you will remember.The Cat house, so called because of the original cathead...
Featured review
Stayed at this gem before and after Lobster mini season. The pool was perfectly refreshing after a day in the sun on the water. There are several free boat ramps nearby. Great proximity to the Looe key...
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Bitter End Vacation Rental –This Summerland Key beauty is the one you have been looking for. Located on Summerland Key with superb boating and access to deep water. Just the perfect spot to see sunset views and peaceful water vistas. Feel free to bring your pet along too!!The interior is...
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Welcome to Pirates Quay! This newly remodeled 2 bedroom home in Little Torch Key is one of the nicest, most thought-out properties in the area, and with extra living space downstairs and plenty of storage, it feels much bigger than it is. Its pirate theme can be seen throughout from the decor, colors...
Distance to beach: 6 miles to Baja Honda
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Conchcanary is located on Little Torch Key, in the heart of the Florida Keys. Come relax in our hammocks with a tropical beverage or bring your boat for some fantastic fishing.Enjoy your morning coffee with a canal views from the screened balcony. Newly updated kitchen with top of the line appliances,...
Featured review
My wife and I spent the first 7 days of our married life living it up in the Keys. We loved it. Kayaking in the bay. Trips to the beach (very different from other beaches). Snorkeling in the ocean! Live...
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Mermaid House was just recently renovated and is a brand new second level vacation rental! This home is in a great central location, not far from Winn-Dixie, Bahia Honda State Park and Key West!Decorated with a warm coastal feel, this home has an open floor plan with large glass windows! The home...
Featured review
I cannot say enough good things about our month-long stay at Mermaid House, so I'll keep it simple, just book it!!! The outside living area was our most favorable spot. (There is one caveat... be VERY...
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Welcome to Yellowstone by the Sea! A spacious, two bedroom, two bathroom, vacation rental home located on Big Pine Key with excellent, quick, open water access. This home truly has the “Keys” vibe inside and out. Plenty of space to relax and chill canal side or poolside! The open concept kitchen,...
Distance to beach: 10 miles to Bahia Honda
Key Amenities
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Our spacious custom built 2 bedroom and 2 bathroom newly renovated home awaits you. Located in the heart of the National Key Deer Wildlife Refuge. On the water with direct access to the Gulf of Mexico or to the Atlantic Ocean. Concrete Seawall with step down easy boat and kayak access. Fish Cleaning...
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This extraordinary island castle will make you feel like the royal family! With four bedrooms and five bathrooms you will not have to share your space! Start your day boating, fishing or kayaking and then return for a cool dip in the pool! Relax on the expansive screened in porch with a drinks and appetizers...
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You and your family will feel right at home in this charming Big Pine Key home. The Owners have totally refurbished this 2 bedroom plus den, 2 bath property in 2020. Soft sea colors and coastal décor make this a totally comfortable home away from home.Large and spacious living room, kitchen and...
Key Amenities
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This unique home is situated on a quiet street, with a desirable corner canal location in Port Pine Heights, Big Pine Key. Bringing your boat along? No problem, plenty of dock space here! And quick and easy access to Pine Channel for excellent boating, fishing, diving and snorkeling!The exterior has...
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Beau Soleil is located in the most sought after neighborhood in the Lower Florida Keys, Summerland Cove, on Summerland Key. A gorgeous gem, tucked away in privacy with tropical plants and fruit trees everywhere you turn!This home is situated on a great boating canal with plenty of dockspace for your...
Distance to beach: 8 miles to Bahia Honda State Park in the keys
Key Amenities
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Ocean access waterfront canal with 40’ dock and all the fixins. Looe key reef straight out canal. 2/2 house with nice size porch
Featured review
Let me start with the owner Vicki, she is wonderful! So responsive, helpful, and friendly. Now for the house....don't know where to start but to say we loved it. Great size and the sliding door in the living...
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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