A coastal residential area with a beach, roads, and a marina.

Englewood Holiday Rentals

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Our top choices for Englewood holiday rentals

1. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
8.8 out of 10, Excellent, (31 reviews)
"Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away. Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!"
United States
Niovys
The price is NZ$1,093
includes taxes & fees
19 Oct - 20 Oct
Chadwick Cove Resort & Marina

2. Paradise in the heart of Old Englewood Village

Paradise in the heart of Old Englewood Village
Olde Englewood Village
10.0 out of 10, Exceptional, (3 reviews)
"Nicest Hosts, very accommodating. Actually went and visited their band at the White elephant and wound up having a great time hanging out while we came for the Englewood Waterfest Boat Races. The place was super clean and the backyard is like none you've ever seen before with nice garden walk and view to the back you would never expect. Very beautiful and very cool. We will definitely return to this location rather than staying anywhere else when we're down that way from now on. So worth it and...
United States
yvette l.
The price is NZ$192
includes taxes & fees
20 Oct - 21 Oct
Paradise in the heart of Old Englewood Village

3. Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Englewood South
10.0 out of 10, Exceptional, (6 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is NZ$419
includes taxes & fees
18 Oct - 19 Oct
Charming 2-bedroom house in Englewood with WiFi and AC

4. Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Englewood Central
10.0 out of 10, Exceptional, (16 reviews)
"Great stay for our family of 5!"
United States
Shawn G.
The price is NZ$422
includes taxes & fees
24 Oct - 25 Oct
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

5. Coastal Quadruplex on Manasota Key, Dog and Snowbird-Friendly Studio (Unit D)

Coastal Quadruplex on Manasota Key, Dog and Snowbird-Friendly Studio (Unit D)
Manasota Key
8.6 out of 10, Excellent, (4 reviews)
"Location great. Clean. Could have been more clear how to access the beach."
United States
Jack
The price is NZ$618
includes taxes & fees
13 Nov - 14 Nov
Coastal Quadruplex on Manasota Key, Dog and Snowbird-Friendly Studio (Unit D)

6. Path to Paradise.

Path to Paradise.
Olde Englewood Village
9.6 out of 10, Exceptional, (7 reviews)
"Great little spot!"
United States
Matthew
The price is NZ$489
includes taxes & fees
19 Oct - 20 Oct
Path to Paradise.

7. Nautical Nook

Nautical Nook
Englewood
10.0 out of 10, Exceptional, (14 reviews)
"We loved our stay and it was perfect for our trip to explore the beaches and parks in the area. Clean spacious and had everything we needed. Very nice owners with extra touches of hospitality! Love this gem and will be back!"
United States
Tracie
The price is NZ$448
includes taxes & fees
24 Oct - 25 Oct
Nautical Nook

8. Enjoy old Florida charm in our cozy beach cottage, dog friendly - minutes to all

Enjoy old Florida charm in our cozy beach cottage, dog friendly - minutes to all
Englewood Central
9.0 out of 10, Wonderful, (7 reviews)
"We enjoyed the quaint little beach house. Not far from the beach. Plenty of places to go shopping and eating. Highly recommend it."
United States
kinz s.
Enjoy old Florida charm in our cozy beach cottage, dog friendly - minutes to all

9. Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
Englewood
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful property"
United States
Erin S.
The price is NZ$530
includes taxes & fees
17 Oct - 18 Oct
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

10. Turtle Cay at The Beach Shack! Come On Down!

Turtle Cay at The Beach Shack! Come On Down!
Manasota Key
10.0 out of 10, Exceptional, (47 reviews)
"This was such a cute place to stay rhat is conveniently located via walking diatance to the beach and local restaurants. "
United States
Renay S.
The price is NZ$663
includes taxes & fees
22 Oct - 23 Oct
Turtle Cay at The Beach Shack! Come On Down!

11. Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs
Englewood
10.0 out of 10, Exceptional, (54 reviews)
"It was a relaxing and beautiful stay!"
United States
Samantha I.
The price is NZ$530
includes taxes & fees
16 Oct - 17 Oct
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

12. Bayfront Condo, Prime Beach Access, Manasota Key

Bayfront Condo, Prime Beach Access, Manasota Key
Manasota Key
9.4 out of 10, Exceptional, (22 reviews)
"Excellent place to stay! Would definitely stay again."
United States
Justin B.
The price is NZ$665
includes taxes & fees
19 Oct - 20 Oct
Bayfront Condo, Prime Beach Access, Manasota Key

13. Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
Englewood
10.0 out of 10, Exceptional, (51 reviews)
"The stay was, as usual, very nice! I can’t say enough about how wonderful the management team is here!! Outstanding!! See you next year!!"
United States
Chris N.
The price is NZ$529
includes taxes & fees
17 Oct - 18 Oct
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

14. Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
Englewood
10.0 out of 10, Exceptional, (64 reviews)
"The location was so convenient to the beaches. Very relaxing and a great place to go to truly feel like you are in a tropical oasis."
United States
Thomas
The price is NZ$530
includes taxes & fees
16 Oct - 17 Oct
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

15. Canal house in Englewood with kayaks close to beaches, springs & attractions!

Canal house in Englewood with kayaks close to beaches, springs & attractions!
Englewood South
The price is NZ$732
includes taxes & fees
29 Oct - 30 Oct
Canal house in Englewood with kayaks close to beaches, springs & attractions!

16. Tranquil and close to Englewood beach

Tranquil and close to Englewood beach
Englewood South
9.8 out of 10, Exceptional, (10 reviews)
"Clean and the Host was great! Will stay again!"
United States
Rob M.
The price is NZ$410
includes taxes & fees
18 Oct - 19 Oct
Tranquil and close to Englewood beach

17. Waterfront Condo Walkable to Everything with Beach Access

Waterfront Condo Walkable to Everything with Beach Access
Manasota Key
9.6 out of 10, Exceptional, (50 reviews)
"Really enjoyed stay here! Great area convenient to bars restaurants and beautiful beach"
United States
Jennifer f.
The price is NZ$763
includes taxes & fees
17 Oct - 18 Oct
Waterfront Condo Walkable to Everything with Beach Access

18. Coastal Chic 2BR | Gulf & Bay Access | Sleeps 6

Coastal Chic 2BR | Gulf & Bay Access | Sleeps 6
Manasota Key
Coastal Chic 2BR | Gulf & Bay Access | Sleeps 6

19. Serene Retreat - 5 mins to Beach, with Beach Gear, Firepit, Bicycles

Serene Retreat - 5 mins to Beach, with Beach Gear, Firepit, Bicycles
Englewood Central
10.0 out of 10, Exceptional, (18 reviews)
"We only stayed one night, but had a wonderful experience. The house is immaculate, and has everything you need. Loved our stay, we will stay again when we are back in town"
United States
Deborah C.
Serene Retreat - 5 mins to Beach, with Beach Gear, Firepit, Bicycles

20. 3 Bedroom- Beachfront Condo with Amazing Sunset Views of the Gulf

3 Bedroom- Beachfront Condo with Amazing Sunset Views of the Gulf
Manasota Key
9.4 out of 10, Exceptional, (87 reviews)
"Wish we could have stayed longer We will definitely be back"
United States
Kendra
The price is NZ$811
includes taxes & fees
17 Oct - 18 Oct
3 Bedroom- Beachfront Condo with Amazing Sunset Views of the Gulf
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Englewood Hotel Reviews

Find out more about Englewood

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Englewood holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Englewood. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Englewood. Seeing all the best attractions is bound to make you fall in love with Englewood. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Englewood short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a holiday rental in Englewood?

Yes, there are holiday rentals close to the most popular sights in Englewood, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the popular beaches in Englewood. Make sure you have time to check out the parks while you're in the area.

What are some of the best holiday rentals that Englewood has to offer?

Large Beach Side Townhouse Condo with views of Gulf. Steps to the beach!: This highly rated holiday home rental in Englewood is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other homes for rent in Englewood include Newly Remodeled-Beachfront Home with Pool/Spa! Private Island Living on 1 Acre and Beachside Bliss: Family-Friendly.

How many holiday rentals are there in Englewood?

Choose from 413 Expedia holiday rentals in Englewood for a memorable holiday.

What can I see and do in Englewood?

Blind Pass Beach and Lemon Bay are a couple of scenic spots to enjoy the outdoors, whereas Lemon Bay Playhouse is one of the cultural attractions. Other places in town to visit include Manasota Beach and Englewood Beach.

What are holiday rentals like in Englewood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Englewood. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a family getaway.