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
9.2 out of 10, Wonderful, (26 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
The price is CA $206
CA $851 total
includes taxes & fees
Sep 12 - Sep 13
Chadwick Cove Resort & Marina

2. Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is CA $586
CA $1,415 total
includes taxes & fees
Sep 13 - Sep 14
Gulf View Condominiums

3. The Suites at Fishermen’s Village

The Suites at Fishermen’s Village
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,318 reviews)
"Great place"
United States
Nidia
The price is CA $206
CA $230 total
includes taxes & fees
Sep 13 - Sep 14
The Suites at Fishermen’s Village

4. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (677 reviews)
"Great stay!!"
United States
Genghis
The price is CA $254
CA $287 total
includes taxes & fees
Sep 20 - Sep 21
A Beach Retreat

5. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,442 reviews)
"This place was perfect!"
United States
Kat
The price is CA $152
CA $172 total
includes taxes & fees
Sep 13 - Sep 14
Hibiscus Suites - Gateway to Siesta Key

6. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,859 reviews)
"This place is awesome, super clean close to the beach and the pool small But completely renovated and great"
United States
Diana
The price is CA $187
CA $247 total
includes taxes & fees
Sep 27 - Sep 28
Tropical Beach Resorts

7. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (178 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
The price is CA $281
CA $318 total
includes taxes & fees
Oct 6 - Oct 7
SeaSpray Resort

8. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (281 reviews)
"Is was a great place to stay, everything was perfect!"
United States
Tracie Costello
The price is CA $153
CA $190 total
includes taxes & fees
Oct 7 - Oct 8
Casey Key Resort

9. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,306 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is CA $199
CA $248 total
includes taxes & fees
Sep 13 - Sep 14
Captiva Beach Resort

10. Home < 1-mi Walk to Warm Mineral Springs Park!

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
The price is CA $207
CA $615 total
includes taxes & fees
Sep 18 - Sep 19
Home < 1-mi Walk to Warm Mineral Springs Park!

11. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (384 reviews)
"Great place"
United States
Mario
The price is CA $106
CA $307 total
includes taxes & fees
Sep 13 - Sep 14
Tiny House Siesta

12. MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Overall, very friendly Gave me advice about the area Told me what live bands were playing that night Very fun definitely will be back"
United States
Kyle
The price is CA $246
CA $521 total
includes taxes & fees
Sep 21 - Sep 22
MALU LANI Inn & Marina

13. Siesta Vibe Pool Walk To Crescent Beach

Siesta Vibe Pool Walk To Crescent Beach
2.0 star property
South Village
The price is CA $165
CA $538 total
includes taxes & fees
Sep 14 - Sep 15
Siesta Vibe Pool Walk To Crescent Beach

14. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (45 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is CA $125
CA $418 total
includes taxes & fees
Sep 13 - Sep 14
Siesta Heron Suites & Villas

15. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is CA $526
CA $958 total
includes taxes & fees
Oct 6 - Oct 7
Siesta Heron 6 / Sunset

16. Coastal Breeze Siesta Entire 4-unit Complex With Dock

Coastal Breeze Siesta Entire 4-unit Complex With Dock
2.0 star property
Siesta Key
The price is CA $1,049
CA $2,712 total
includes taxes & fees
Sep 21 - Sep 22
Coastal Breeze Siesta Entire 4-unit Complex With Dock

17. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

Explore Sarasota: Condo w/ Pool Access, Near Dtwn
3.5 star property
Sarasota
The price is CA $131
CA $396 total
includes taxes & fees
Sep 13 - Sep 14
Explore Sarasota: Condo w/ Pool Access, Near Dtwn

18. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is CA $1,120
CA $1,497 total
includes taxes & fees
Oct 2 - Oct 3
Beach Road

19. Siesta Sands Beach Resort Gulf View

Siesta Sands Beach Resort Gulf View
2.5 star property
South Village
10.0 out of 10, Exceptional, (1 review)
"Loved to property! Clean and accommodating. Had a beautiful ocean view and could walk right out to the beach. Pool area was clean."
United States
Jessica
The price is CA $455
CA $1,044 total
includes taxes & fees
Oct 8 - Oct 9
Siesta Sands Beach Resort Gulf View

20. Beach Road - Capri

Beach Road - Capri
2.5 star property
Siesta Key
Beach Road - Capri
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?

Newly Remodeled-Beachfront Home with Pool/Spa! Private Island Living on 1 Acre: 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. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind. Some other homes for rent in Englewood include Large Beach Side Townhouse Condo with views of Gulf. Steps to the beach! and FLASH SALE - just steps to beach. 2BR/1BA.Dogs welcome! Perfect ratings..

How many vacation rentals are there in Englewood?

Choose from 431 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.