
Holiday rentals in Spanish Harbor Key
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Top-rated holiday rentals in Spanish Harbor Key
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Other great holiday rentals in Spanish Harbor Key

Home in Summerland Key
4.83 out of 5 average rating, 58 reviewsKelly’s Kabin - Private FL Keys Cottage
LadyRating, 5 stars4 weeks ago
The cabin was cozy and super cute. It was impeccably clean. I only stayed one night but wish I stayed longer. She had all the necessary amenities. I didn’t get to use the patio since I mostly stayed out on the boat but wish I had more time to do so. Kristin had board games, shampoo, conditioner, body wash, blow dryer, washer, dryer and everything you would want in an AirBNB. There are plenty of restaurants nearby and the supermarket wasn’t too far. I felt safe in the neighborhood. I hope to come back and stay here again!

Holiday home in Big Pine Key
5 out of 5 average rating, 5 reviewsBoater dream home 75ft wide crystal clear canal
KathyRating, 5 stars15 months ago
My husband and I, along with some friends, stayed the month of March. The description of the house is accurate; clean, homey, comfortable beds, nice furnishings and decorated nicely. A few minor issues came up while we were there and Kelly & Walter responded very quickly to resolve! We kayaked/paddle board with manatees in the canal right outside our front door, to include different kinds of fish. I enjoyed my morning runs on the bike/walking trail at the end of our street. Also, met many nice neighbors as well while walking our dog. The weather was beautiful, only rained 3 days the entire time we were there. The boat lift and pool were a plus, after a day of boating we would come back and cool off in the pool. We enjoyed our stay so much, we have already booked March of next year!!! Thank you Kelly & Walter for sharing your home with us!

Home in Summerland Key
5 out of 5 average rating, 4 reviewsA month in paradise pool home.
LOUISERating, 5 stars10 months ago
We spent a month at this beautiful home. From open water the view, to the boating access, the amazing sunset and the pool, the place was perfect for us! We love the lower keys and this was the ideal place to spend a month. Tracy was always responsive answering any questions we had. I can't recommend enough. We hope to return in the future!

Campervan/Motorhome in Big Pine Key
4.71 out of 5 average rating, 14 reviewsRV In The Keys | Tropical Retreat
TalitaRating, 5 stars2 days ago
We had a fantastic stay at for our anniversary! The trailer was filled with everything you need during your stay — we cooked dinner, hung out, watched TV, and had a great night of sleep. It was very accommodating, especially since we brought along our two dogs. The location was perfect, and we appreciated how pet-friendly and welcoming everything was. And how close it was to anything we needed it. One of the most memorable parts of our trip was being able to get super close to the local baby deer. They were incredibly friendly and loved the attention — a truly special experience that we’ll never forget. We booked this place to spend Saturday at the sandbar at Content Key, which was absolutely a dream — phenomenal place that made our trip extra memorable. Heather was incredibly responsive and helpful, providing us with all the information we needed for a smooth and enjoyable stay. Highly recommend for anyone looking for a relaxing getaway in Big Pine Key. We can’t wait to return!

Campervan/Motorhome in Big Pine Key
4.85 out of 5 average rating, 13 reviewsIsland Girl Big Pine Key
JaneRating, 5 stars1 week ago
Enjoyed dealing with Corinne and staying at her place.
Superhost

Home in Cudjoe Key
4.88 out of 5 average rating, 34 reviewsWaterfront FL Keys Cottage @ Venture Out
KeeleyRating, 5 stars4 days ago
This was a great place to stay to experience the beauty of the Florida Keys. The pool, hot tub, and amenities are very well worth it, and the location and proximity to Key West is a huge plus as well. Very relaxing and accommodating!
Guest favourite

Home in Big Pine Key
5 out of 5 average rating, 6 reviewsCozy Waterfront Key Deer Retreat
KatherineRating, 5 stars1 month ago
Beautiful, Beautiful Beautiful did I say Beautiful. you won't be disappointed if you rent this house, so private and quiet. yes the neighbors are close but they weren't home our entire stay and we wouldn't have noticed if they were there, there was to much to do and see. So easy and close to a marina to put your boat in the water for 10$ each day In and Out. The Rooster was perfect for many dinners. Boondocks 10 minutes away for a little competitive putt putt, live music,and great food. Shopping galore Key West just 30 minutes away. Oh yes and the house was Beautiful, the beds were comfy, extremely clean and everything to make your vacation great is right here. The Key Deer are a bonus. Thank you Estrella we will be back.

Cottage in Cudjoe Key
4.9 out of 5 average rating, 155 reviewsATLANTIS...Ocean Front Cottage Retreat!
WendyRating, 5 stars1 month ago
We had an amazing 6-night stay at this waterfront Airbnb! The location is perfect—right on the water with gorgeous sunrise views. We used the provided kayaks every day, and my husband loved fishing off the deck while I relaxed in the sun. The house is super cute, clean, and beachy. The bed was very comfortable, and the kitchen was well-stocked with basics like spices and oil, making it easy to cook most of our meals. We also appreciated the strong, hot shower and provided toiletries. Extras like beach towels, umbrellas, fishing gear, and a washer/dryer made our stay even better. The area is peaceful, clean, and friendly—plus, Key West is just a short drive away. We’d definitely stay here again!
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