8 Best Long-Term Rentals In Big Pine Key, Florida

Deanna
Deanna 
Updated
| 3 min read

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) Superhost status. recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on November 28, 2023.

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.

Stayed at this property?
Big Pine Key, Florida, United States
PRIVATE VACATION HOME 10 Guests 3 Bedrooms 2 Bathrooms

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

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.

Stayed at this property?
Big Pine Key, Florida, United States
72 reviews   Wifi Available
Tiny home 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
we had a very comfortable stay
Cleanliness:
very clean comfortable and safe
now clean place well maintained and next to a pool
the place was nice and clean
the house was comfortable and clean
the place itself is beautifully clean and peaceful - perfect for our family of four
Host:
friendly hosts i felt very welcomed and great communication
the price was right compared to hotels on key west hosts alex and vikki are excellent
Location:
the location was close to restaurants stations and the main attractions
great tiny house in a cute rv park we loved our stay
it was in a trailer park and all the neighbors were friendly
easily walkable to locally recommend restaurant and grocery store
great little place to stay right in between everything fun in the keys
Read more reviews

3. Cozy boat house in Old Wooden Bridge Resort and Marina (from USD 182)

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.

Stayed at this property?
Big Pine Key, Florida, United States
122 reviews   Wifi Available
Houseboat 2 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Cleanliness:
the place was very clean
the house boat was very clean and built with meticulous detail
awesome experience great location and cleanliness is on point
Host:
office staff had everything i could ask for and were very helpful
the management was very friendly and helpful and offered a number of useful local tips
the people that work there are friendly and helpful recommend some great food spots
lots of wild friendly deer and lizards too
the bridge yields excellent fishing (especially at night) and the staff are all so nice and helpful
Location:
perfect location for all we wanted to do
but for me the location greatly exceeded my expectations and the plus is succeeded the minuses
perfect location with easy access to key west local eateries and right on the bay minutes from the ocean
aqualodges at owb marina are a great location for boating and kayaking in the northern keys
Read more reviews

4. Spacious family home with canal views (from USD 159)

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.

Stayed at this property?
Big Pine Key, Florida, United States
PRIVATE VACATION HOME 6 Guests 2 Bedrooms 2 Bathrooms

Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

5. Elevated duplex with shared deck (from USD 93)

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.

Stayed at this property?
Big Pine Key, Florida, United States
79 reviews   Wifi Available
ENTIRE RENTAL UNIT 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
it is a nicely sized one bedroom apartment with a fully equipped kitchenette
no fan in the bathroom but a great shower beds were adequate and plenty of linens and towels
nothing wrong with the room itself
Cleanliness:
unit was clean and accurately described
it was clean and met out needs
the space was very clean an adequate
it was clean except for the floors could have been mopped better as our feet got black
communication and check in was great and the place was super clean
Host:
staff were all very pleasant and helpful
staff very nice and helpful robin and sandy
host was very tentative and friendly great place
robin the host couldn't have been more helpful
very friendly accommodating and very helpful
Location:
super location and comfortable accommodations
location is nice with the deer though
nice location has everything you need
nice location to anywhere in florida key
great location by the ocean
Read more reviews

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.

Stayed at this property?
Big Pine Key, Florida, United States
4 reviews   Superhost Wifi Available
ENTIRE HOME 6 Beds 8 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Host:
the house was amazing the host was communicative and made the process super easy highly recommend
stephanie was extremely responsive for any issue at all resolving it immediately
Location:
good snorkeling close by too
great location between key west n marathon
it's a nice house with lots of space and a great location
Read more reviews

7. Glamping camper with friendly neighbors (from USD 162)

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.

Stayed at this property?
Big Pine Key, Florida, United States
106 reviews   Wifi Available
Camper/RV 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
bed and pull out couch were comfortable
the ac was very cold and comfortable
Cleanliness:
it was clean
whole place is clean and well equipped
this camper was clean comfortable and cozy
camper was clean and had all the necessities needed
great time the rv was very clean and capt
Host:
rick was a great host
place is comfortable host very responsive
the accommodation was comfy and safe neighbors nice n friendly
captain rick is very helpful and was always available t answer questions
captain rick was on the ball with all instructions and helpful hints throughout our stay
Location:
great location for local activities and just a short distance to key west
great location right outside of key west
very comfortable and great location
good location for my free divings class
there is also a nice restaurant within walking distance and several that are a short drive away
Read more reviews

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.

Stayed at this property?
Big Pine Key, Florida, United States
27 reviews   Wifi Available
Camper/RV 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the wifi and cell service was excellent
camper was modern exquisitely clean cozy and the amenities were good
Cleanliness:
great vibe clean & quite with a homey feel
the rv was perfect it was clean and comfortable to be in
Host:
our host was awesome
daniel is a great host
he’s a great host and a kind man
landlord is kind and very accommodating
daniel was very helpful and informative
Location:
great accommodations and great location
great affordable place whether you’re adventure takes you to marathon or key west
Read more reviews

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.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Deanna Kathrina, a pediatric physical therapist specializing in neurodevelopmental disability, serves as a teacher and advocate. As a lifelong learner, she enjoys the company of music and aspires...Read more

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