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

Englewood Vacation Rentals

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Our top choices for Englewood vacation rentals

1. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
8.8 out of 10, Excellent, (30 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 CA $214
CA $878 total
includes taxes & fees
Oct 2 - Oct 3
Chadwick Cove Resort & Marina

2. 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, (5 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is CA $100
CA $333 total
includes taxes & fees
Oct 2 - Oct 3
Charming 2-bedroom house in Englewood with WiFi and AC

3. Coastal Manasota Key Quadruplex, Dog-Friendly Studio, Snowbird Specials (Unit C)

Coastal Manasota Key Quadruplex, Dog-Friendly Studio, Snowbird Specials (Unit C)
Manasota Key
10.0 out of 10, Exceptional, (2 reviews)
"This place has everything! Chris was friendly and helpful. I loved the location with a short walk to the beach and a view of the bay on the back porch. I will absolutely return"
United States
Christy S.
The price is CA $91
CA $416 total
includes taxes & fees
Oct 2 - Oct 3
Coastal Manasota Key Quadruplex, Dog-Friendly Studio, Snowbird Specials (Unit C)

4. 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, (2 reviews)
"We had an excellent stay and would absolutely recommend this property. The home was exceptionally clean, well-maintained, and very comfortable throughout our visit. It was clear that the owners take great pride in keeping the property in top condition.Everything was exactly as described, and we felt right at home from the moment we arrived. The comfortable accommodations and attention to cleanliness made our stay relaxing and enjoyable. We would gladly stay here again and highly recommend it to...
United States
Andrew D.
The price is CA $96
CA $153 total
includes taxes & fees
Oct 7 - Oct 8
Paradise in the heart of Old Englewood Village

5. 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 CA $134
CA $415 total
includes taxes & fees
Oct 19 - Oct 20
Path to Paradise.

6. 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 CA $240
CA $526 total
includes taxes & fees
Oct 18 - Oct 19
Turtle Cay at The Beach Shack! Come On Down!

7. 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)
"Very clean house, nice place to stay"
United States
Linda G.
The price is CA $111
CA $356 total
includes taxes & fees
Oct 17 - Oct 18
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

8. Nautical Nook

Nautical Nook
Englewood
10.0 out of 10, Exceptional, (13 reviews)
"Great place to stay and very spacious. Heather was a"
United States
Paul
The price is CA $148
CA $368 total
includes taxes & fees
Oct 19 - Oct 20
Nautical Nook

9. Bayfront Condo, Prime Beach Access, Manasota Key

Bayfront Condo, Prime Beach Access, Manasota Key
Manasota Key
9.4 out of 10, Exceptional, (16 reviews)
"Excellent place to stay! Would definitely stay again."
United States
Justin B.
The price is CA $176
CA $528 total
includes taxes & fees
Oct 4 - Oct 5
Bayfront Condo, Prime Beach Access, Manasota Key

10. Turtle Bay 1A – Manasota Key Gulf & Bay Retreat | Beach, Pool & Bay Dock

Turtle Bay 1A – Manasota Key Gulf & Bay Retreat | Beach, Pool & Bay Dock
Manasota Key
9.8 out of 10, Exceptional, (22 reviews)
"Great location with easy access to beach, bay and restaurants. "
United States
Steve A.
The price is CA $109
CA $719 total
includes taxes & fees
Oct 2 - Oct 3
Turtle Bay 1A – Manasota Key Gulf & Bay Retreat | Beach, Pool & Bay Dock

11. 2-bedroom pool house with golf cart in Englewood, close to the beaches!

2-bedroom pool house with golf cart in Englewood, close to the beaches!
Grove City
10.0 out of 10, Exceptional, (10 reviews)
"Great stay, great host, and a great time!"
United States
Christopher G.
The price is CA $177
CA $431 total
includes taxes & fees
Oct 12 - Oct 13
2-bedroom pool house with golf cart in Englewood, close to the beaches!

12. Englewood Inn & Suites

Englewood Inn & Suites
Englewood South
The price is CA $185
CA $235 total
includes taxes & fees
Oct 12 - Oct 13
Englewood Inn & Suites

13. 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
9.8 out of 10, Exceptional, (6 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.
The price is CA $107
CA $382 total
includes taxes & fees
Oct 12 - Oct 13
Enjoy old Florida charm in our cozy beach cottage, dog friendly - minutes to all

14. 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)
"Excellent stay at Pura Vida——-clean, cool rooms, very relaxing experience on the property. It’s obvious Pura Vida put thought into the arrangement of outside amenities, including couches, dining tables, the spa, and numerous fruit trees planted around the property. Would 100% stay here again."
United States
Alex
The price is CA $141
CA $444 total
includes taxes & fees
Oct 17 - Oct 18
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

15. CLEAN,Great Location,Dockage Available,HEATED Pool, HUGE Back yard. Unit C

CLEAN,Great Location,Dockage Available,HEATED Pool, HUGE Back yard. Unit C
Grove City
9.8 out of 10, Exceptional, (8 reviews)
"Great place. Clean and comfortable. Communication with host was quick and easy."
United States
Christian O.
The price is CA $192
CA $466 total
includes taxes & fees
Oct 2 - Oct 3
CLEAN,Great Location,Dockage Available,HEATED Pool, HUGE Back yard. Unit C

16. Flamingo's Nest at the Beach Shack. Just one block from the beach!

Flamingo's Nest at the Beach Shack. Just one block from the beach!
Manasota Key
10.0 out of 10, Exceptional, (44 reviews)
"Location was great, property condition is excellent!"
United States
Mabel
The price is CA $239
CA $529 total
includes taxes & fees
Oct 19 - Oct 20
Flamingo's Nest at the Beach Shack. Just one block from the beach!

17. Blissful Beach Retreat A, Close to Beaches, Dog-Friendly, Private Deck

Blissful Beach Retreat A, Close to Beaches, Dog-Friendly, Private Deck
Manasota Key
The price is CA $135
CA $654 total
includes taxes & fees
Oct 3 - Oct 4
Blissful Beach Retreat A, Close to Beaches, Dog-Friendly, Private Deck

18. 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)
"Property managers were very helpful to work with and will still stay again despite a hiccup. "
United States
Jennifer J.
The price is CA $149
CA $617 total
includes taxes & fees
Oct 2 - Oct 3
Waterfront Condo Walkable to Everything with Beach Access

19. 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 CA $128
CA $327 total
includes taxes & fees
Oct 5 - Oct 6
Tranquil and close to Englewood beach

20. Coastal Quadruplex on Manasota Key, Dog-Friendly, Snowbird Specials (Unit B)

Coastal Quadruplex on Manasota Key, Dog-Friendly, Snowbird Specials (Unit B)
Manasota Key
The price is CA $135
CA $655 total
includes taxes & fees
Oct 10 - Oct 11
Coastal Quadruplex on Manasota Key, Dog-Friendly, Snowbird Specials (Unit B)
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Englewood?

Yes, we have vacation rentals close to popular points of interest in Englewood, or you can go with a more remote option if you want a relaxing place to 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 vacation home rentals that Englewood has to offer?

Large Beach Side Townhouse Condo with views of Gulf. Steps to the beach!: This highly rated vacation home rental in Englewood is located on the beach and has a balcony, a garden, and a barbecue grill 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 vacation rentals are there in Englewood?

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

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 vacation rentals like in Englewood?

Vacation rentals are privately owned accommodations you can reserve for several days or longer in Englewood. Vacation rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family trip.