Apartment holiday rentals in Big Pine Key

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Popular amenities for Big Pine Key apartment rentals

Weekly apartment rentals

Guest favourite
Flat in Marathon
5 out of 5 average rating, 15 reviews

"O" Fish Ally Paradise @Ocean Isle Fishing Village

AmyRating, 5 stars2 weeks ago
Ocean Isles is a beautiful property. Very quiet and calm. Everyone we encountered was so friendly. Great views! Nice amenities and property had box of fun extras…we had to leave a couple behind to add to the stash. Great communication. We definitely will be booking again in the future.
Flat in Islamorada
4.78 out of 5 average rating, 46 reviews

Poolside 2 queen Apartment

ElizabethRating, 5 stars3 weeks ago
We had a great time at Breezy Palms with just me and my daughter! The poolside apartment was so squeaky clean, tidy, and just lovely. The bed was very comfortable. We had everything we needed. We will definitely be back with the entire family.
Guest favourite
Flat in Key West
4.91 out of 5 average rating, 11 reviews

Duval Corner - Pet friendly with Balcony

ValerieRating, 5 stars1 week ago
We had a great time in Key West and love that we had the option to bring our pups while we stayed here! Was so happy to discover the sofa is a pull out sleeper. The host was able to accommodate a last minute change of plans, which we are so grateful for. There was always an open free parking spot on the street. The location was a short walk to everything you’d want to see! Thank you for a great stay and going above and beyond to accommodate us!
Guest favourite
Flat in Marathon
4.94 out of 5 average rating, 16 reviews

Relax with the whole family at this peaceful place

CourtneyRating, 5 stars5 days ago
Came for a week and were pleasantly surprised how centrally located it was. Walking distance to Publix and Walgreens! There’s lots to do in area. Check in was very easy. The walk into building on the one side was blocked by construction but you can get into inside of building on both sides so not big deal at all. Parking was right out front of screened porch which made coming and going easy. She had chairs in closet to take to beach which we were thankful for. She always responded to questions fast and was very helpful. Even with construction the areas very quiet. We didn’t spend lot of time at condo as we had family in town . 2 of grown kids came in for few days to stay with us and we were comfortable with 4 adults. Freezer has ice maker but we bought extra ice for drinks . We enjoyed our stay and would love to come back to stay here again! Recommendations: bike works in marathon had best deals on evokes and great way to get around!
Flat in Key West
4.87 out of 5 average rating, 30 reviews

Apartment at Safe Harbor Marina

DrewRating, 5 stars1 week ago
This is our second time staying at this location and it honestly couldn’t be any better. The people around the marina are very friendly and inviting and the host is very responsive. We look to return soon.
Guest favourite
Flat in Marathon
5 out of 5 average rating, 6 reviews

Boot Key Harbor Penthouse

DennisRating, 5 stars4 months ago
Wonderful views, quiet. Clean and had free laundry. Just what we were looking for. Beautiful property with balcony, patio and rooftop deck. Centrally located and close to shopping Good places to eat nearby
Flat in Key West
4.77 out of 5 average rating, 43 reviews

Charming, updated home near Duval St.

JessicaRating, 5 stars1 month ago
The apartment was easy to book, easy to find and easy to access. It is in the middle of the island (east-to-west), just off Duval St. (the main drag), so it is very convenient. I rented a bicycle for transportation during my stay, and the fenced, gated, secure patio was the perfect parking spot when I was "home." The interior was clean, comfortable and beachy. It had everything I needed with the expected luxury-accommodation quality. Do note that there is no dishwasher or clothes washer/drier, but I knew this ahead of time, so it was no problem. The management office is just around the corner, and they have a nice service where you can drop off your luggage for day-storage if you arrive prior to check-in time.
Flat in Islamorada
4.88 out of 5 average rating, 51 reviews

Endless Bay Views, Sues Promise Islamorada FL

LaurenRating, 5 stars3 weeks ago
Absolutely awesome spot. The dock is a little reef itself and is covered in parrotfish, grouper, and snapper. Easy docking! Couldn’t have asked for anything more.

Private apartment rentals

Flat in Key West
4.8 out of 5 average rating, 15 reviews

Shipyard 208-6 condo in Truman Annex-2 bed 2 bath

TomRating, 5 stars5 months ago
This place is great in Key West. It's close to bars and restaurants but removed enough to be quiet at night. Just get bikes and the island is yours! Lovely place with space for all you need.
Superhost
Flat in Key West
4.88 out of 5 average rating, 1,506 reviews

At Mine | Lovely Suite steps from Duval Street

JessicaRating, 5 stars3 days ago
We absolutely LOVED our stay here. The location on Angela St was the perfect walking or biking distance from Duval St without it being too noisy at night! The rooms were super clean and smelled great! They let us put our luggage in their storage room when we got there early so we could begin exploring! The pool was leisurely and the perfect temperature! There are tons of good restaurants and bars in the area! 10/10 HIGHLY RECOMMEND this place. We will most definitely be back!
Guest favourite
Flat in Key West
4.89 out of 5 average rating, 109 reviews

Duval Street Suites full kitchen Old Town with hea

RichardRating, 5 stars1 week ago
The location of the apartment could not have been in a better place. Easy access to the apartment from the rear of the building through the parking lot in Pool area to the front of the apartment on Duval Street. The apartment was immaculately kept. The bed and the pullout couch was very comfortable
Guest favourite
Flat in Key West
4.91 out of 5 average rating, 800 reviews

Duval Balcony Spanky's Retreat

SteveRating, 5 stars2 weeks ago
Cool vibe, great location, excellent value.
Superhost
Flat in Key West
4.83 out of 5 average rating, 236 reviews

#204 Key West Suites

ChristopherRating, 5 stars1 month ago
Great spot, Everett was easy to get ahold of and we were able to check in early by messaging them.
Top guest favourite
Flat in Key West
4.93 out of 5 average rating, 116 reviews

Duval Street Suites full kitchen, free parking, &

LoganRating, 5 stars6 days ago
Was a super great location and a beautiful room, Had a bit of a problem in the middle of the night but she rushed right over when we let her know and she solved it right there and then super worth it will definitely stay again
Guest favourite
Flat in Key West
4.87 out of 5 average rating, 724 reviews

Duval Balcony - Suite Mischief

MattRating, 5 stars2 weeks ago
Can’t say enough good things about Tom this place. He was responsive and friendly with any question we had. Location was great for exploring Key West. Felt like you were in the middle of everything but still private. The deck was fantastic to sit on and watch Duval Street. We can’t wait to stay again.
Guest favourite
Flat in Key West
4.91 out of 5 average rating, 280 reviews

Starr's Suite - 2 person K Suite w/Private Spa!

AndreaRating, 5 stars2 weeks ago
Great location! Super close to duval street but really private. We rented a scooter and went everywhere. I do recommend emptying out the air dehumidifier if you’re staying a couple of nights so it’s always running. We would love to stay again

Apartment rentals with a hot tub

Guest favourite
Flat in Key West
4.9 out of 5 average rating, 58 reviews

Castaway Cove: Pet-friendly 2/2 condo near beach!

AllieRating, 5 stars5 days ago
This is exactly the kind of stay we were hoping for. The building is in a very quiet and safe area. About a 10 min and $15-20 uber to Duval st. The space was very clean and spacious for our group of 3 + dog. The pool was never crowded and the general store in walking distance has everything you need. THE VIEW OF THE SUNSET IS UNMATCHED! Do yourself a favor and stay at Mike’s place if you ever find yourself on island time.
Flat in Key West
4.68 out of 5 average rating, 123 reviews

Hot Tub & Pet Friendly - Royal Palm

Margo Rating, 5 stars2 months ago
We previously stayed on this property in the upstairs apt and liked the convenience to everything. Across the street is Ramshead Live. Down the block is Blue Heaven and other amazing restaurants. This space is secluded and we loved the hot tub. The bed was also very comfortable.
Top guest favourite
Flat in Key West
5 out of 5 average rating, 43 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

BrennanRating, 5 stars1 month ago
We loved our stay with Teri and Scott! Nice location convenient to the airport. Beautifully renovated. Was just what I needed for a group of 4-6. Thanks again yall!
Top guest favourite
Flat in Key West
5 out of 5 average rating, 14 reviews

Heron Hideaway

FaduaRating, 5 stars5 days ago
We loved our time here! Place was super cute and felt just like home. Super clean and close to everything. Host was flexible with out check out time which we really appreciated. Would love to stay here again. Thanks again!
Superhost
Flat in Key West
5 out of 5 average rating, 4 reviews

Hyatt Windward Pointe! Great Location!

MelissaRating, 5 stars3 months ago
Beautiful place with a well stocked unit…close enough to all the places we wanted to visit, yet far enough away for a quiet, relaxing day. We loved the area and our stay here. Thank you, Chris.
Guest favourite
Flat in Key West
5 out of 5 average rating, 5 reviews

Henry's Penthouse On The Ocean

WilliamRating, 5 stars1 month ago
The Condo was spacious, beautiful, well furnished, very clean and the location was perfect. Henry was great to work with. We rented a golf cart and traveled almost everywhere in Key West by golf cart.
Superhost
Flat in Key West

The Galleon Resort - Key West

TonyRating, 5 stars5 months ago
Very nice place and Craig was very easy to deal with.
Guest favourite
Flat in Key West
5 out of 5 average rating, 9 reviews

Downtown KeyWest 2Bed Oceanfront

KendraRating, 5 stars1 week ago
Samantha was a great host. We had to call the front desk for extra bedding and to fix the ac, they were extremely helpful and fulfilled our requests within minutes. We would stay here again. Location is close to everything so walking was a breeze.

Quick stats about flat rentals in Big Pine Key

  • Total rentals

    10 properties

  • Nightly prices starting at

    $64 SGD before taxes and fees

  • Total number of reviews

    460 reviews

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

  • Local attractions

    No Name Pub, National Key Deer Refuge and The Big Pine Key Flea Market

Destinations to explore

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  4. Monroe County
  5. Big Pine Key
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