Cottage holiday rentals in Casey Key, Florida

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Popular amenities for Casey Key, Florida cottage rentals

Cottage rentals with a hot tub

Guest favourite
Cottage in Captiva
4.86 out of 5 average rating, 90 reviews

Cottage Secluded in Palms 1 minute walk to Beach

AmberRating, 5 stars5 days ago
Great stay. There were some minor problems but communication was good and things were taken care of.
Guest favourite
Cottage in Holmes Beach
4.93 out of 5 average rating, 57 reviews

Close to the Beach+ Private heated pool and spa!

StacieRating, 5 starstoday
This is our third stay on AMI at this exact property, and - I don’t know how Craig does it - but every trip to Kiwi Cottage gets even better! The house, pool and grounds are beautiful. We are a family of 4 and brought two friends of our daughters’ this year, and even with more people, the house and pool felt spacious and comfortable. The girls and their friends absolutely loved the location, and paired ice cream with beach sunsets every night this past week. We also rented their golf cart, which was super convenient for dinners (Harry’s on Father’s Day was a favorite) and exploring the island (especially bc it fits 6 people)! Always an amazing week on AMI at Kiwi Cottage! We’re already talking about next time. Craig is a great host and extremely friendly and responsive! He’s always available for questions and recommendations - we feel so lucky that we found this listing years ago, and can’t wait to come back again.
Superhost
Cottage in Cape Coral
4.63 out of 5 average rating, 49 reviews

Villa The Island Hideaway 2

JamieRating, 5 stars3 months ago
Wow! We loved this house. Great outdoor seating, loved watching the boats come and go. Pool and hot tub were fantastic. Great flat grill for dinners at home. Good restaurant options in the area. Cape Coral is close to so much, but away from traffic. Loads of windows and natural light. Very clean. Highly recommend.
Guest favourite
Cottage in Fort Myers
5 out of 5 average rating, 6 reviews

Boutique retreat in heart of River District w/spa

KellyRating, 5 stars2 days ago
This was a beautiful, peaceful cottage! It was exactly as described and portrayed in photos. Impeccably clean with so many extra amenities it felt like a concierge-level hotel stay. The couch and bed were both very comfortable, the hot tub clean and private, and the front porch swing a cozy place to enjoy the garden and birds. Good location if you plan to visit the Edison and Ford Estate. Close to downtown restaurants (walking distance, but I did wish I'd brought my bike instead). Nice walk to park on the river.
Top Guest favourite
Cottage in Sarasota
4.99 out of 5 average rating, 88 reviews

Quaint Cottage,150 steps away from Crescent Beach!

JohnRating, 5 stars1 month ago
From the moment we arrived at this top-rated “Quaint Cottage,” we knew we’d found something special. This charming retreat sets the bar for excellent stays. Inside, every detail felt outstanding—from the freshly laundered linens and plush towels to the fully equipped kitchen that made cooking a breeze. Madeline’s communication was first-class, offering clear check-in instructions and local recommendations that turned our weekend into a seamless escape. Every little touch—from the high-speed Wi-Fi to the thoughtful supply of beach chairs and umbrellas—was superior… the gold standard of hospitality. Location-wise, you couldn’t ask for more: just a quick four-minute stroll to Crescent Beach’s powdery white sands, turquoise blue water and deep red, yellow and orange sunsets. Within steps you’ll find a lineup of dining options—fresh seafood at waterfront restaurants, laid-back bars serving sunset cocktails, and cozy cafés perfect for post-beach coffee. In every way, our stay was awesome!
Superhost
Cottage in Bradenton
4.91 out of 5 average rating, 76 reviews

Sandy Cottage w/ Hot Tub, 20 min to Beach + Garden

TafeeRating, 5 stars2 months ago
This is a BEAUTIFUL place. There was a lovely welcome basket with toiletries when we arrived. Lots of fun board games. The back patio with hot tub are incredible, at night it is amazing. The host was really proactive in communicating with us, and was a pleasure to work with. Very, very quiet inside as well. With 2 bunk beds in the 2nd bedroom, you have lots of options. My son kept begging us to stay another day! We would highly recommend this location to anyone.
Guest favourite
Cottage in Sarasota
4.76 out of 5 average rating, 131 reviews

Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub

MeredithRating, 5 stars1 week ago
This cottage was perfect for me, my husband, and our baby girl. We had the pool to ourselves the whole time, which isn’t guaranteed but was great. Weather was perfect. The beach is so close and so nice. The area has beautiful, large homes, which made for nice scenery when we walked. I really liked the location of this place vs the north end of Siesta Key. It was less crowded and very easy to navigate places. Dave, the property manager, was amazing. He was very informative, friendly, responsive, and helpful.
Guest favourite
Cottage in Sarasota
4.97 out of 5 average rating, 35 reviews

Charming Coastal Oasis 2 Bed/2 Bath Cottage

LisaRating, 5 stars2 weeks ago
The house was perfect! We enjoyed every moment of our stay. The pool was the perfect touch! Definitely would come again!

Pet-friendly cottage rentals

Guest favourite
Cottage in Holmes Beach
5 out of 5 average rating, 18 reviews

Palm Villa by Beach Boutique Rentals

TanjaRating, 5 stars2 months ago
We had a wonderful week at Beach Boutique's Anna Maria Island Cottages. The cottage is very cute and tastefully decorated. The kitchen had the necessary supplies, although we also explored the local restaurant scene and used it mostly for breakfast. Despite being situated close to a street, it was quiet and peaceful. The small set of cottages that makes up the property also has several private nooks and a little fountain with more seating areas. We appreciated having access to laundry facilities on-site. The location is also pretty walkable to a few shops and restaurants. We 100% enjoyed a calm, relaxing week away from New England March weather, went for swims and long walks on the beach, enjoyed magnificent sunsets and recharged our batteries.
Top Guest favourite
Cottage in Englewood
4.94 out of 5 average rating, 83 reviews

Private garden cottage

DavidRating, 5 stars1 week ago
I stayed to be near heritage oaks assited living. It was perfect. flexible. comfortable. clean accommodations for my needs. Angelika was great. Friendly and helpful.
Top Guest favourite
Cottage in Bradenton
5 out of 5 average rating, 31 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

KellyRating, 5 stars1 week ago
We stayed at this home for 2 weeks and the nature watching was fascinating. Alligators, turtles, birds and fish jumping out of the water. The home was comfortable and included everything one would need. The Wi-Fi was solid for zoom calls and remote work. The kitchen had every dish, pot, utensil for cooking. The AC worked great and the beds were super comfy. The host replied quickly to every question. I would stay here again. 5 stars. ⭐️ ⭐️⭐️⭐️⭐️
Superhost
Cottage in Bradenton
4.85 out of 5 average rating, 103 reviews

Casa Azul. 2 bed/2 bath on lake

ChaseRating, 5 stars2 weeks ago
Very nice place. Close to all the major attractions in the area. My family enjoyed the stay!
Top Guest favourite
Cottage in Placida
4.98 out of 5 average rating, 48 reviews

West Coast Island Retreat, Simply Adrift Cottage

CourtneyRating, 5 stars1 month ago
By far the most relaxing vacation our family has taken. The home is even more beautiful in person than the pictures show. The host's style and decor are just perfect for a cool beachy vibe which adds to the whole experience of being on LGI. Hosts were extremely accommodating during our stay. We cannot wait to return! ☀️
Guest favourite
Cottage in Bradenton
4.98 out of 5 average rating, 86 reviews

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

JuliaRating, 5 stars3 weeks ago
This was our second summer in a row staying at the cottages. We always have a blast.
Top Guest favourite
Cottage in Englewood
5 out of 5 average rating, 12 reviews

2 bdrm, walk to beach, 2 bikes & kayaks, grill

CindeeRating, 5 stars6 days ago
This place is beautifully decorated and is by far the cleanest vacation rental that we have ever stayed at! We did not want to leave! Easy walk to the uncrowded beach, just as in the description. One big surprise was finding HOT water in the outdoor shower, which was very welcomed. Everything needed is provided, including bath soap, shampoo, conditioner and K-cups for the Kuerig! We can't wait to go back, hopefully for a longer stay! Thank you!
Superhost
Cottage in Bradenton
4.89 out of 5 average rating, 9 reviews

Studio competely remodeled

TracyRating, 5 stars5 days ago
The unit was located in a beautiful, quiet neighborhood. Parking was right in front. Lots of pretty trees. Interior was nicely decorated with everything you could need including a hair dryer & coffee maker. Bed & couch were comfy. We really enjoyed our stay here.

Private cottage rentals

Top Guest favourite
Cottage in Arcadia
5 out of 5 average rating, 100 reviews

Quaint Cottage w/access to Peace River canoe/kayak

DanielRating, 5 stars3 days ago
Our time at Horse Creek Retreat with Marc and Meagan was fantastic. They were very accommodating hosts and were always available if we had a question or need. The property was private and beautiful and the amenities were very enjoyable. The cottage was outfitted with all the kitchen-ware that we needed and was comfortable (with strong AC 😁). It definitely was the get-away that we were hoping for - we hope to come back!
Guest favourite
Cottage in Englewood
4.89 out of 5 average rating, 129 reviews

Good after Milton - Kayaks & Steps to Beach-pc

ChrisRating, 5 stars10 months ago
Amy is a terrific host and always on hand with local suggestions, additionally to the comprehensive package at the property. The property itself is in an amazing location, with just a 60 second walk to the beach and bath like sea! To help, Amy provides all the kit needed for the beach with chairs, parasols and towels easily to hand. The kitchen is great with all cooking implements you need and the living room has a massive TV with all the required streaming services logged in. I would definitely recommend Amy as a host!
Superhost
Cottage in Bradenton
4.79 out of 5 average rating, 95 reviews

Cozy! near restaurants, beaches, airport & more

LaurenRating, 5 stars5 days ago
Host was responsive, friendly, and willing to allow our family to stay and check-in rather late in the evening when we had to vacate our prior arrangements unexpectedly. Her place was clean, matched description and photos, and exceeded expectations.
Guest favourite
Cottage in Palmetto
4.96 out of 5 average rating, 94 reviews

Historic 1930s Palmetto Cottage

AlbertoRating, 5 stars6 days ago
We had a truly wonderful experience staying at this Airbnb! The place was spotless, beautifully decorated, and even better than the photos. The host was very helpful and made sure we had everything we needed for a comfortable stay. The location was perfect and close to everything, but quiet and relaxing. We would absolutely stay here again and highly recommend it to anyone looking for a great getaway!
Top Guest favourite
Cottage in Bradenton
4.96 out of 5 average rating, 69 reviews

Cheerful 2 bedroom , plus bunk room vacation home.

LaneRating, 5 stars1 week ago
This was a great stay for our family of 5 while visiting the Sarasota area. Beds were comfy, extra pillows and blankets available, very well stocked kitchen. AC worked great. We did have a small issue with the bunk beds not being made and a coverlet that was dirty. The host was quick to respond and even refunded part of our cleaning fee to compensate us. We were pleased with how it was handled. Don’t miss visiting The Ringling (plan to spend all day), Caspersen Beach (for shark teeth), the point of Anna Maria Island (for tons of huge shells and beautiful beaches with lots of wildlife). We also really liked this little neighborhood. Be sure to walk around the corner to meet Sheldon the tortoise.
Cottage in Sarasota
4.81 out of 5 average rating, 248 reviews

Cozy Cottage by the Bay

PamelaRating, 5 stars5 days ago
cottage was comfortable and easy access to everywhere we needed to go
Guest favourite
Cottage in Siesta Key
4.88 out of 5 average rating, 316 reviews

Cottage on Siesta Key Beach

CherylRating, 5 stars1 week ago
This whimsical beach cottage was exactly what we needed after Hurricane Milton. The house was stocked with everything we needed to feel at home. The beds were comfortable and the location was perfect. It was unfortunate to see the devastation from the hurricane around the property, but thankfully Andrew’s place was seemingly untouched. We’re very happy for you! Thank you for providing a great place to enjoy the bay and the beach!
Guest favourite
Cottage in Sarasota
5 out of 5 average rating, 106 reviews

Chic Sarasota Cottage: Near Beaches & Downtown!

KarenRating, 5 stars1 week ago
Our third time staying at this wonderful cottage, we love it. It is spacious, quiet, nicely decorated, and has very comfortable furnishings. With a fully stocked kitchen and washer & dryer it is like a home away from home.

Destinations to explore