Big Pine Key is the largest island of the lower Florida Keys. Located 100 miles (161 kilometers) south of Miami, this tourist destination offers fun diversions such as snorkeling, diving, and fishing. In this tropical oasis, you will have your fill of inspired seafood dishes. It is also known as the home of Key Deer. This endemic and endangered species is the smallest subspecies of white-tailed deer on the continent. For an extended exploration of the Lower Keys, you can book vacation homes close to crystal blue waters and accommodations surrounded by forests and wetlands. Read on to find out about the best long-term rentals in Big Pine Key, Florida.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on April 14, 2024.
1. Sprawling property with boat dock (from USD 485)
Choose this fenced property with lush trees in the yard and a boat dock up front. Avid anglers only have to take a short walk to a bridge used by locals for fishing. A popular pub where you can make new friends is also nearby. Guests here have access to cooking and laundry amenities. Fast WiFi is available for work and play. You can also spend time hanging out in the property’s heated pool.
2. Pet-friendly house in Breezy Pines RV Resort (from USD 228)
Book this vacation rental and experience living in a tiny house with an outdoor lounging area. The house is only 10 feet (3 meters) from the community pool of Breezy Pines RV Resort. The interior features a full kitchen and a grill on the patio. A small family will feel at home in this air-conditioned property. Guests may park one car for free and rent bikes and kayaks for a surcharge.
Top guest reviews
Amenities & Room:
we had a very comfortable stayCleanliness:
very clean comfortable and safenow clean place well maintained and next to a poolthe place was nice and cleanthe house was comfortable and cleanthe place itself is beautifully clean and peaceful - perfect for our family of fourHost:
friendly hosts i felt very welcomed and great communicationthe price was right compared to hotels on key west hosts alex and vikki are excellentRead more reviewsLocation:
the location was close to restaurants stations and the main attractionsgreat tiny house in a cute rv park we loved our stayit was in a trailer park and all the neighbors were friendlyeasily walkable to locally recommend restaurant and grocery storegreat little place to stay right in between everything fun in the keys
3. Cozy boat house in Old Wooden Bridge Resort and Marina (from USD 199)
Embrace island living fully in this unique long-term rental unit. Kayak and boat rentals are readily available. Try your hand at fishing and use the fish cleaning station to prepare your catch for grilling. The campfire pit is next to the fenced saltwater pool. Guests will find clean and furnished rooms inside the property, including a sizeable master bedroom and an equipped kitchen.
The front deck is directly over the water and is the best spot to watch sunsets on Big Pine Key.
Top guest reviews
Cleanliness:
the place was very cleanthe house boat was very clean and built with meticulous detailawesome experience great location and cleanliness is on pointHost:
office staff had everything i could ask for and were very helpfulthe management was very friendly and helpful and offered a number of useful local tipsthe people that work there are friendly and helpful recommend some great food spotslots of wild friendly deer and lizards toothe bridge yields excellent fishing (especially at night) and the staff are all so nice and helpfulRead more reviewsLocation:
perfect location for all we wanted to dobut for me the location greatly exceeded my expectations and the plus is succeeded the minusesperfect location with easy access to key west local eateries and right on the bay minutes from the oceanaqualodges at owb marina are a great location for boating and kayaking in the northern keys
4. Spacious family home with canal views (from USD 187)
Take a nap in a hammock for ultimate relaxation in the outdoor area fronting the water. Then, you can regroup in the spacious open-plan living area of this property. The towels in the bathroom are new. The washer is in the pantry room and there is a clothesline in a covered area on the ground floor. Pots, pans, and utensils for cooking three meals a day are provided. Your month-long stay here will definitely be comfortable.
5. Elevated duplex with shared deck (from USD 211)
This cabin on the right side of a duplex promises a calm interlude for you and your fur baby. The main door is accessible via a staircase with rails. Pack light for a month-long stay. The host will stock the bathroom and kitchen for you. The yard and deck area are shared with the neighboring unit. You can observe the goings-on in the marina from the deck. Guests here may use the picnic area and saltwater pool of the resort.
Top guest reviews
Amenities & Room:
it is a nicely sized one bedroom apartment with a fully equipped kitchenetteno fan in the bathroom but a great shower beds were adequate and plenty of linens and towelsnothing wrong with the room itselfCleanliness:
unit was clean and accurately describedit was clean and met out needsthe space was very clean an adequateit was clean except for the floors could have been mopped better as our feet got blackcommunication and check in was great and the place was super cleanHost:
staff were all very pleasant and helpfulstaff very nice and helpful robin and sandyhost was very tentative and friendly great placerobin the host couldn't have been more helpfulvery friendly accommodating and very helpfulRead more reviewsLocation:
super location and comfortable accommodationslocation is nice with the deer thoughnice location has everything you neednice location to anywhere in florida keygreat location by the ocean
6. Summery cottage on the canal (from USD 225)
Give your family a chance to experience island living in this remodeled cottage near the Spanish Harbor. Stay a month or more in this pleasant abode with a covered porch and waterfront bedrooms. Bikes and kayaks will be on hand for exploring the charming neighborhood. You may bring your boat and tie it down in front of this well-appointed rental unit. If the weather is fine, you can sail to the ocean for deep-water fishing.
Top guest reviews
Host:
the house was amazing the host was communicative and made the process super easy highly recommendstephanie was extremely responsive for any issue at all resolving it immediatelyRead more reviewsLocation:
good snorkeling close by toogreat location between key west n marathonit's a nice house with lots of space and a great location
Superhost
7. Glamping camper with friendly neighbors (from USD 231)
Experience a smooth-sailing holiday in this upscale camper. One of the highlights of this property is the roomy bathroom, which is a rare feature to come across in an RV.
You can make coffee daily and bake treats in the oven while staying in this air-conditioned recreational vehicle. There are two steps going into the bedroom with a queen bed. Take your shoes off before entering the camper and go up three steps to find a binder inside with suggestions for making your month-long stay worthwhile.
Top guest reviews
Cleanliness:
it was cleanwhole place is clean and well equippedthis camper was clean comfortable and cozycamper was clean and had all the necessities neededgreat time the rv was very clean and captHost:
rick was a great hostplace is comfortable host very responsivethe accommodation was comfy and safe neighbors nice n friendlycaptain rick is very helpful and was always available t answer questionscaptain rick was on the ball with all instructions and helpful hints throughout our stayRead more reviewsLocation:
great location for local activities and just a short distance to key westgreat location right outside of key westvery comfortable and great locationgood location for my free divings classthere is also a nice restaurant within walking distance and several that are a short drive away
8. Spotless camper with shared pool (from USD 119)
Take this opportunity to call a well-kept camper your home for at least a month. Cross out towels, bedsheets, and plates from your list of things to pack. This recreational vehicle also boasts central air-conditioning and reliable WiFi. Moreover, there is a kitchen and grill for cooking. You are likely to meet Key deer on your way to the shared swimming pool nearby. The gracious host will welcome you and show you how the buttons and gears work.
Top guest reviews
Amenities & Room:
the wifi and cell service was excellentcamper was modern exquisitely clean cozy and the amenities were goodCleanliness:
great vibe clean & quite with a homey feelthe rv was perfect it was clean and comfortable to be inHost:
our host was awesomedaniel is a great hosthe’s a great host and a kind manlandlord is kind and very accommodatingdaniel was very helpful and informativeRead more reviewsLocation:
great accommodations and great locationgreat affordable place whether you’re adventure takes you to marathon or key west
Cherish island living in Big Pine Key
The Lower Keys of Florida are known for beaches, endemic wildlife, and rich marine resources. The island called Big Pine Key is a wonderful place to spend an extended holiday. Book one of these long-term accommodations that are close to nature and enjoy everything that Big Pine Key has to offer.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to