Cottage vacation rentals in Englewood

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Popular amenities for Englewood cottage rentals

Pet-friendly cottage rentals

Cottage in Venice
4.73 out of 5 average rating, 130 reviews

Cozy Florida Cottage

ClodeenRating, 5 stars2 weeks ago
Perfect location to collect shark teeth at the nearby beach and check out the Warm Mineral Springs not to far away! Benjamin was super responsive to my messages and very helpful. The place was spotless upon arrival. We enjoyed our stay and would happily come again!
Top guest favorite
Cottage in Placida
4.98 out of 5 average rating, 45 reviews

West Coast Island Retreat, Simply Adrift Cottage

AdamRating, 5 stars1 month ago
We had a great time staying here! The home was beautiful with all the beach supplies one could want. As someone who drove their boat up, the dock had great cleat availability and we had no problems getting a spot. One of the easier places to dock at that I have stayed overnight. Home also has everything for cooking and good wifi for being on an island. Loved the vibe of LGI, watching the sunset, and exploring the surrounding islands. Would definitely stay again!
Superhost
Cottage in Sarasota
4.65 out of 5 average rating, 17 reviews

Charming Bungalow | Close to Beach | 2 Beds

SusanRating, 5 stars4 months ago
Adorable, spotless duplex on a quiet street. One of the best properties I have ever rented. Hosts are responsive and pleasant. Will rent again when in the area.
Guest favorite
Cottage in Fort Myers
5 out of 5 average rating, 5 reviews

Ft.Myers Bliss: Walk to Best Eats & Shops!

EricRating, 5 stars3 weeks ago
Met my mom and sister for a weekend stay at the Cracker Cow Cottage. The home is spotless, adorable and well thought out. We had everything we needed. All the attention to detail shows the host(s) really care about their guest. Michelle is very attentive and is excellent at her job. Highly recommend.
Top guest favorite
Cottage in Sarasota
5 out of 5 average rating, 36 reviews

Cozy Cottage near Siesta Key Beach

JoyRating, 5 stars1 month ago
We thoroughly enjoyed our stay at Canopy Cottage. This was our second year staying and loved it even more. Jami is an excellent host. We loved being close to the Legacy Trail to ride bikes and the sort drive to Siesta Key Beach! Would definitely stay again.
Top guest favorite
Cottage in Little Gasparilla Island
4.98 out of 5 average rating, 54 reviews

Happily Ever After

HollyRating, 5 stars4 days ago
We had a wonderful stay. Very unique house and surroundings. We walked to the beach for a beautiful sunset and enjoyed the screened porch. Will definitely recommend!
Cottage in Fort Myers
4.58 out of 5 average rating, 12 reviews

Little Cottage on the Field

TomiRating, 5 stars13 months ago
Very nice house in a quiet neighborhood. The entire process was hassle-free. We won’t hesitate to book again the next time we come to Fort Myers!
Guest favorite
Cottage in Sarasota
4.97 out of 5 average rating, 33 reviews

Charming Coastal Oasis 2 Bed/2 Bath Cottage

CindyRating, 5 stars3 weeks ago
We loved Lara's place, and she was extremely easy & quick to communicate with. We love the quiet neighborhood and the pool was the cherry on top! We will definitely be reserving her sweet home again!

Private cottage rentals

Guest favorite
Cottage in Englewood
5 out of 5 average rating, 14 reviews

Casa Amistad 1 - Third House From the Beach

RhondaRating, 5 stars9 months ago
This is a lovely home with astounding amenities. The street is old Florida style mixed with newer homes. The beach and water are heaven. There really are no words to describe. The home, street, and beach are jewels….and the host is amazing!! This neighborhood is very quiet and so peaceful.
Guest favorite
Cottage in Bokeelia
4.85 out of 5 average rating, 87 reviews

The Bokeelia Cottage

VanessaRating, 5 stars3 weeks ago
This tini home is great! We had two very nice days - the area is super calm! Out neighbour was a gator - so don’t go for a swim 🫢🙂
Guest favorite
Cottage in Siesta Key
4.95 out of 5 average rating, 77 reviews

Surf Shack- Walk to Village/Boat Dock Included

BlakeRating, 5 stars2 weeks ago
We had a wonderful stay at Jim’s place! The location is perfect—just a short walk to the beach and close to everything you need. The home itself is beautiful, clean, and comfortable, with everything thoughtfully set up for a relaxing getaway. What made the stay even better was Jim himself—he’s incredibly kind, welcoming, and great to talk to. You can really tell he cares about making sure his guests have a great experience. We’d absolutely stay here again and highly recommend it to anyone visiting the area!
Guest favorite
Cottage in Nokomis
4.83 out of 5 average rating, 48 reviews

The "Sun Cottage" - your relaxing interlude!

KellyRating, 5 stars4 months ago
We love the Sun Cottage. This is our second stay there. A really nice place. Within walking distance or short drive to the beach. Lauren responded to our questions very quickly. We stayed two months so we really appreciated the washer/dryer and the stocked kitchen. We would definitely book again.
Top guest favorite
Cottage in Englewood
4.98 out of 5 average rating, 52 reviews

Magnolia Cottage

RoseRating, 5 stars2 months ago
Magnolia cottage is in a great location, near two parks on Lemon Bay, two blocks from shopping and restaurants on Dearborn Street, quaint Florida neighborhood. Karmen and Brian are fantastic hosts, friendly and always responsive to our every need. Love staying here. Rose and Jerry
Top guest favorite
Cottage in North Fort Myers
4.92 out of 5 average rating, 85 reviews

Simply Natural Farm Getaway

SidneyRating, 5 stars2 weeks ago
Friendly owners, private location and a clean place to stay. All you could really ask for. If ever in Fort Meyers again, I would certainly look to come here first.
Guest favorite
Cottage in Punta Gorda
4.79 out of 5 average rating, 33 reviews

Historic Themed Cottage Punta (No Cleaning Fee)

AnnamarieRating, 5 starstoday
We had a great stay! Loved that the location was close to the river walk! The unit was very clean, and was decently stocked. Was also a very quiet neighborhood. The host was responsive and put together some nice guides for the area. I'd stay here again if I need a rental in Punta Gorda.
Top guest favorite
Cottage in Osprey
4.96 out of 5 average rating, 51 reviews

Mattie’s Cottage by the Bay

MaryRating, 5 stars3 weeks ago
We absolutely loved our stay at Todd and Marie’s lovely home. We’ve stayed in many Airbnb’s and this one stands out as one we felt completely at home. The bed was extremely comfortable, the linens crisp and clean. The kitchen was perfectly appointed. The sweet front and back porches were great places to hang out morning and evening. The air conditioning units worked beautifully on hot days. But the windows on the front porch worked well letting in cool morning breezes. The walk around the neighborhood and short walk to the water were covered with extraordinary live oak trees. We discovered a fun tiki bar with great music and food just down from the house. However, with that said, it was extremely quiet at the house. The location was perfectly situated off the main route 41 connecting the beach towns and found it easy to get around to get to the beaches on the Gulf. I highly recommend this airbnb.

Luxury cottage rentals

Guest favorite
Cottage in Sarasota
4.83 out of 5 average rating, 41 reviews

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

AlisonRating, 5 stars2 weeks ago
We had a wonderful vacation at the Siesta Beach Cottages. The property was exactly as described in the listing. The condo very clean and had everything my family of 4 needed for a week’s vacation - beach chairs, beach towels, bikes, grill, washer/dryer, bedsheets, towels, and full kitchen. Neighborhood was quiet and neighbors were friendly. Communication about the property, amenities, and location, and nearby activities made the stay stress-free! Cottages are within short walk to the beautiful beach and restaurants. Thanks for a great vacation, can’t wait to return!
Cottage in Nokomis
4.86 out of 5 average rating, 14 reviews

Private Beachfront Casey Key Cottage B

JennyRating, 5 stars2 months ago
what you are paying for here is the location and it is truly astonishing- a private beach, sand between your toes. it's absolutely glorious. the place has everything you need- big fridge and washing machine a bonus- but it's falling asleep to the sound of the waves that makes it really really special.
Cottage in Siesta Key
4.23 out of 5 average rating, 13 reviews

3 Bedroom Beach Front Cottage

ChaseRating, 5 stars9 months ago
This place is a hidden Gem. The cottage is beautiful and the location can't be beat. The place was clean and had everything we needed including tons of beach chairs and umbrellas and toys for the kids. Path to the beach in your backyard is hard to beat and make it really convenient for us with the kids. Check in and check out we're was smooth as silk, and travis was very responsive and in making us feel at home. Worth every penny and made great memories with tbe family, I highly recommend this one!
Superhost
Cottage in Cape Coral
4.8 out of 5 average rating, 5 reviews

Cape Lake House Lake Front

KelseyRating, 5 stars3 weeks ago
We had two families and we both enjoyed our stay! The house was very accommodating for both our families with kids. We all enjoyed the salt water pool and patio. The information binder provided gave clear instructions for our stay and provided many recommendations for restaurants and activities to do. Stu and Cathy were very helpful and even personally check on us during our stay!
Cottage in Boca Grande
4.83 out of 5 average rating, 105 reviews

Charming beach cottage house with pool.

AlisonRating, 5 stars1 month ago
We had the BEST week at this cottage. The owners were very gracious, and helped us with whatever we needed. We will definitely look into the cottage for our next stay!! Boca is still very much recovering from the hurricane, but overall I was extremely impressed with how well the island looks.
Top guest favorite
Cottage in Sarasota
4.99 out of 5 average rating, 85 reviews

Quaint Cottage,150 steps away from Crescent Beach!

FrankieRating, 5 stars2 weeks ago
We’ve stayed near Siesta key before, but the experience was very different this time due to our host. Starting before we arrived, she made sure we would have what we needed for our staff, including a high chair and crib. During our stay she checked in regularly. It felt more like we were staying at a friends house than a rental.
Cottage in Siesta Key
5 out of 5 average rating, 9 reviews

Charming Beach Cottage with pool

JolenRating, 5 stars21 months ago
From the moment our tires hit the shell driveway, it felt like coming home! A quick trip across the bridge to Detwiler's Farm Market for groceries and we were set for our week in paradise! The lush tropical setting and beautiful private beach were a constant source of peaceful tranquility, and the pristine pool was the perfect refresher after a lovely day on the beach. Boogie boards for playing in the surf and a tropical gazebo area for a seat in the shade made for hours in a mind-soothing space. Dolphins and even a manatee along with multiple seabirds completed the true tropical vibe! The cottage was the perfect size, super comfy, well appointed with everything you needed and the walk in shower gave us a great idea for a home remodel project! Al, Ilene, and Fannie, (their beautiful dog) thank you for sharing your home and your beautiful paradise with us! We will definitely be back
Superhost
Cottage in Sarasota
4.86 out of 5 average rating, 43 reviews

Siesta Key Cottages Crescent 2B Beach/Pool/Hot Tub

DaleRating, 5 stars25 months ago
Dave took good care of us during our stay. There were a few minor issues but Dave was responsive and quick to get things replaced/fixed. We were in contact throughout the week, which was great. We loved having the bikes and the beach supplies. Pool volleyball and ping pong were a huge hit! We will definitely be coming back next year for our annual family vacation. Marc is easy to get ahold of, informative and helpful. Thank you for hosting us!

Quick stats about cottage rentals in Englewood

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    2.7K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

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  2. United States
  3. Florida
  4. Sarasota County
  5. Englewood
  6. Cottage rentals