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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...
Key Amenities
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Welcome to Kokomo Palms – Your Island Escape!Discover the perfect slice of paradise at Kokomo Palms, a charming 2-bedroom, 1-bath vacation home nestled in Big Pine Key. Located in a peaceful canal-front neighborhood, this getaway offers everything you need for a relaxing and adventurous stay....
Featured review
We had a great time - the rental was terrific! Best clostet space we've ever encoutered. Clean laundry set. Accomadotions were top shelf all around. Nicely seculed & quiet location. And we saw Key deer...
Distance to beach: 8 miles to Bahia Honda State Park in the keys
Key Amenities
About this property
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...
Key Amenities
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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...
Distance to beach: 10 miles to Bahia Honda
Key Amenities
About this property
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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Key Amenities
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The South House is a superb vacation home on Summerland Key. It offers everything you need to make your Florida Keys vacation truly memorable.The downstairs pool area is private and serene. There are several lounging areas to enjoy suntanning or wonderful afternoon shade. The crystal blue pool is...
Key Amenities
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Latitude Adjustment equals attitude adjustment! Location Location Location! This vacation rental home is located in the super desirable Summerland Cove neighborhood, with easy quick open water access!Whether you are coming for the weather, the boating, the diving or just to relax, this home has it...
Distance to beach: 100 feet to our back yard...steps away from the house
Key Amenities
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The Key-ver beach house is an oceanfront vacation rental in the world-famous Florida Keys on the southern end of Summerland Key, mile marker 25. The house is an open floor plan with panoramic Atlantic Ocean views and a large wrap-around deck. Two bedrooms (the oceanside bedroom has a king bed and the...
Featured review
Fantastic location, the view from the sunroom is fantastic. Postcard sunrises to start the day! House was very well equipted with everything we needed during our stay, hosts reached out to check on us...
Key Amenities
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Looking for the perfect getaway for your Florida Keys vacation? Look no further! Tropical Oasis is just the home for you and your guests with only 23 miles to Key West; not that you’ll ever want to leave the beautiful views of the mangroves and sea-life!Tropical Oasis is a two bedroom, two bath...
Key Amenities
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Florida Keys Vacation Rentals – This waterfront home located in Coral Shores Park on Little Torch Key. It is a real paradise pleaser! The spacious interior is nicely decorated and completely remodeled. It has a beautiful open floor plan with views of the expansive deck and open water.There are...
Key Amenities
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Florida Keys Vacation Rentals – Need a private space to call home during your sunny stay in the Florida Keys? Conchy Joe’s is the place! This beautiful home has 3 bedrooms and 2 bathrooms. The interior is fully furnished and decorated in Florida Keys fashion with plenty of space for friends...
Featured review
Always enjoy our stays in Keys when we find such a lovely place to have family come to join us. Some homes have a great location some have great amenities, but finding one like this, that has both is...
Distance to beach: 9 miles to Bahia Honda
Key Amenities
About this property
Enjoy the Florida Keys in this beautiful canal front two bedroom two bath house in a beautiful area on Little Torch Key. The house features a master bedroom with a king size bed, flat screen TV, and the second bedroom also has a king size bed. A well designed and fully equipped kitchen with everything...
Featured review
We enjoyed our stay in this extremely comfortable home. Beds were very comfortable and location was close to lots of restaurants and local attractions. Having a place for our boat was the best. We could...
Key Amenities
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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...
Key Amenities
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The Coral House is a prime destination spot for a great Florida Keys vacation! Conveniently located on Ramrod Key, mile marker 27. Close to all the choice restaurants and services that the Florida Keys have to offer.This home is beautifully decorated in island style with attention to even the smallest...
Key Amenities
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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...
Key Amenities
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Stay where the palm trees meet the ocean. The Egret House is a quaint and charming home nestled in the lower Florida Keys. This spectacular home is in the perfect location in the highly desirable side of the island. Cozy 2 bed, 1 bath property with open water access, heated and cooled saltwater pool,...
Featured review
We stayed from middle of June to middle of July this year and can tell you, you will not find a more relaxing vacation spot that this one. Scott was incredible from the first day we connected until we...
Key Amenities
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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...
Key Amenities
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Welcome to El Paraiso, a true Cudjoe Key gem at an affordable price. This three bedroom, three bath home is nicely updated throughout! Located on Lafitte Drive, right behind the famous Square Grouper restaurant and only 20 minutes from Key West. Don’t forget to bring your boat, there is plenty of...
Distance to beach: 15 miles to Bahia Honda State Park
Key Amenities
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Amenities Galore: Heated pool, hot tub, huge screened in porch, tiki with alexa speaker and hammock, bikes, piano, aerial fitness studio, reverse osmosis drinking water, large TV for streaming, fully stocked kitchen with gas stove. Relaxing blue master bedroom has super comfy king bed and soaking tub....
Key Amenities
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Welcome to Paradise Palm, a home away from home that encourages outdoor fun and relaxation with its unforgettable exterior amenities! Nestled in a quiet neighborhood, this beautifully furnished home offers a perfect blend of comfort and luxury.Step outside and be greeted by an excellent space that...
Key Amenities
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Escape to paradise in this beautiful newly remodeled 2 bedroom 1 bath duplex unit on a canal nestled in the heart of Big Pine Key. Perfectly located near a grocery store, great local restaurants, parks, and just minutes from the famous Bahia Honda State Park. Whether you're looking to relax or head...
Key Amenities
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About the House • 3 bedrooms · 3 bathrooms · 3 beds · Sleeps up to 6 guests • Fully stocked kitchen with stainless steel appliances • Brand-new sheets and duvets for a luxurious sleep • In-unit washer and dryer for your convenience • Ceiling fan &...
Key Amenities
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Welcome to Bow Channel Manor and step back in time to Old Florida! You’ll find this plantation style home remeniscent of Florida past! Enjoy family-style vacationing on a private 4 acre parcel of land on Upper Sugarloaf Key.The grounds are like a playground. There is a full-size heated pool...
Key Amenities
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***We are taking the recommended steps as presented by the Center for Disease Control and Prevention (CDC) for cleaning, disinfecting, and preparing this home for your arrival. We are following the protocols laid out by the CDC and using the EPA-approved disinfectants for Hard (non-porous) Surfaces, Soft...
Featured review
Nice house. Owner was super great to work with. nice pool. road is a little tight for boat and trailer.
Key Amenities
About this property
Welcome to Paradise Blue....a true slice of paradise on Little Torch Key! This private retreat sits on 2 lots with the house on one and the in-ground pool on the other. The lush landscaping provides tons of privacy and truly makes you feel like you're on your own secluded island!Enjoy the day...
Key Amenities
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Newly renovated cottage with million dollar oceanfront views.The beautiful in ground private pool will give the serenity you need for a relaxing escape with unobstructed view of the ocean, you can enjoy breathtaking sunsets, watch boats drift by, and listen to the soothing sounds of the waves—all...
Featured review
I stayed in the newest cottage . It was very clean and every essential needed. Mark was thoughtful enough to put bottles of water in the refrigerator for us . I had coffee every morning on the upper Tiki...
Key Amenities
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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...
Key Amenities
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Beautiful Ocean Front Home with six bedroom/Four bath. New memory foam mattresses in King and Queen rooms. Enjoy the heated pool, dock and beach. Located on Cudjoe Bay with panoramic view of the Atlantic and deep water swimming. Kayaks are provided for your enjoyment. There is a huge screened in porch...
Featured review
We enjoyed a family vacation for one week at this "villa". The view was spectacular and the interior spacious. There were plenty of spaces for all of us to sit and visit with each other. The pool was fun...
Key Amenities
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Clean, Tropical 3/2 on open canal in quiet residential neighborhood on a cul-de-sac. House is on Gulfside with quick access to Miles Channel Bridge towards ocean or bayside. 50’ concrete dock with fish cleaning station.Master Bedroom has a queen size bed, shower and indoor jacuzzi tub. Second...
Featured review
Alex and I had a wonderful time in your beautiful home. Loved eating dinners (breakfast and lunch too!) sitting outside. Peaceful and lovely. The storage room downstairs was perfect for storing all our...
Distance to beach: 10 miles to Bahia Honda, Key West
Key Amenities
About this property
Wonderful, pet-friendly and beautifully decorated 3/2 home on the water that's perfect for a vacation or simply relaxation. It's located on beautiful Cudjoe Gardens with direct ocean access. There's a marina within walking or rowing distance. Check out the nearby Marvin Key video.Summary: •...
Featured review
My husband and myself along with another couple rented this property for 28 days in September 2022. The home is clean, very comfortable and nice. There is a canal at the house which we used to dock 2 boats...
Key Amenities
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Come live the Salt Life at Salty Retreat! Stay at this luxury top of the Line tropical style home on Summerland Key. Located in a very popular subdivision on Lagoon Drive with deep boating access.This home is 'five stars' the moment you pull into the paver circular driveway. Sitting on two...
Key Amenities
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3 bedroom 3 bathroom home on canal with heated pool and room for a 25' boatMaster Bedroom: King bed with TV, private bathGuest Bedroom: Queen Bed with TV3rd Bedroom: Queen bed , sleeper sofa, Tv mini kitchenOur pricing is based on four guests. Additional guests will be charged...
Key Amenities
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Welcome to the Snow Grouper, a classic and comfortable vacation rental home in the much sought after Summerland Cove on Summerland Key.This home is a two-bedroom, two-bathroom up, and a one bedroom full apartment downstairs, and is completely remodeled, with a layout that is welcoming, from the open...
Distance to beach: 15 miles to Bahia Honda State Park
Key Amenities
About this property
28-NIGHT MINIMUM RENTAL — PLEASE READ BEFORE INQUIRINGMonroe County requires a minimum rental of 28 consecutive nights to a single family or party. No subleases are permitted. We cannot accept reservations for fewer than 28 nights.This requirement is strictly non-negotiable. Monroe County...
Featured review
The home was clean and full of amenities. Great place to spend a month escaping harsh Wisconsin winters. Owners were attentive and easy to deal with. A great boat launch should you need one. Neighborhood...
Key Amenities
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Summerland Escape lives up to the name in every possible way! This oceanfront property offers 2 bedrooms, 2 bathrooms, beautiful living room and dining areas with spectacular ocean views. The well-appointed open concept kitchen with all stainless appliances offers plenty of space for relaxing or entertaining....
Distance to beach: 2 miles to Picnic Island (by Boat)
Key Amenities
About this property
Beautifully kept private and secure canal front (220' of waterfront) home. Located at the end of a dead end street in a residential neighborhood alLows for privacy and extra relaxation. Fully updated kitchen, fully equipped with coffee maker, espresso maker, blender, bullet blender, etc. Ideally...
Featured review
The property is updated, super comfortable, spacious, and beautifully decorated. We will be visiting again!
Key Amenities
About this property
Come stay at this heavenly oasis. Pull up to a fully fenced 2 bedroom, 2 bathroom Florida Keys home. The front parking area provides parking for you AND your guests. In addition, there is plenty of space to park your water toys on the 60’ of dockage.The home offers beautfiul, vaulted wood ceilings...
Key Amenities
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Are you looking for a home on Big Pine Key with open water views? Look no further! This two-bedroom, two-bathroom home has it all. No shortage of outdoor living space here! There are TWO upper decks with equally great views, one is screened in, and both are nicely furnished. The lower level has a hot...
Key Amenities
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Private Beach, ocean front home with pool on Cudjoe Key.Home includes;- Master bedroom suite with 32' flat screen TV, full bathroom including tub and shower for 2, sliders open to private Master Suite deck with ocean view and private beach.- 2 additional bedrooms with Jack-n-Jill bath-...
Featured review
We really enjoyed the large house. The easy to launch kayak area was very convientant. Location was great - 25 minutes to Key West. The sunsets were breathtaking. House was well equipped with every you...
Key Amenities
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Breathtaking sunrises from your balcony at this 3 bedroom, 2 bath home. There's a L shaped floating dock that can host a 24' boat, or you can launch the provided kayaks onsite. The master bedroom has a king bed, a working desk station, balcony access, and a private bath. There is a King bed,...
Key Amenities
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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...
Key Amenities
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Welcome to the “Fish Camp,” a unique Summerland Cove/Key home with multi-family accommodations available. This is a super spacious three bedrooms and two bathrooms upstairs, and one bedroom, one bathroom and a full kitchen downstairs, with top-of-the line appliances! Definite “must see”...
Key Amenities
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This Cudjoe Key home is neat as a pin with all the comforts of home. Bright and shiny kitchen with everything you may need to create wonderful get together. The large comfortable living room has plenty of seating including recliners in the sofa and loveseat. Laminate hardwood floors throughout. 3 large...
Featured review
We thoroughly enjoyed our stay at Palmetto Retreat. The home was spotless and had all the amenities we needed. A couple of menial things didn't work, and Christine (Rudy) took prompt care of them while...
Key Amenities
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Florida Keys Vacation Rentals – “WOW!” is what you will say when you walk through the door of this Little Torch Key home. With cathedral ceilings and a large family and dining area, your whole family will be able to stretch out and relax.The updated kitchen looks out to the canal...
Key Amenities
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This bright, very spacious and inviting, nicely-maintained Sugarloaf Key home is located just 20 minutes north of Key West. Nestled back in a beautifully manicured neighborhood and not far from Sugarloaf Lodge and Marina, you will have nearby access to boating, fishing, kayaking and a few local restaurants.An...
Key Amenities
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Private canal-front home designed for 27+ day stays, offering a quiet, comfortable alternative to high-turnover vacation rentals. Private dock, heated/chilled pool, and just 3 minutes to open water—ideal for boating, fishing, and extended stays. Seasonal summer rate currently offered due to availability.Set...
Key Amenities
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This lovely waterfront home has it all. This fantastic community is one of the most unique places in the world. In minutes you can explore the beautiful back country or Ocean by kayak or boat. Marine Life sightings and fishing is the best in this area. You can lay back and relax, away from it all and...
Featured review
House was perfect for me--quiet and peaceful. Never rented a house with a pool before, but this was wonderful. No mosquitos. Boat dockage was ideal. The fish cleaning table, which I used a lot, needs a...
Key Amenities
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Enjoy the ultimate peace and quiet offered on Big Torch Key. Located just 5 miles off the Overseas Highway. This pristine area is a true treasure of the lower Keys. This home is nicely remodeled and boasts large spacious room and comfortable furnishing.The shady screened porch overlooks the crystal...
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
We came down from Ohio to get away from the cold weather and had a wonderful time in fandango! We really enjoyed the kayaks, the swimming pool and the hot tub! The house had a wonderful kitchen , hot tub...
Key Amenities
About this property
Florida Keys Vacation Rentals – This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features such as hardwood floors and a beautifully well-equipped, custom kitchen. Spacious living and dining rooms provide ideal entertaining...
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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