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Englewood Vacation Rentals

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Our top choices for Englewood vacation rentals

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
$522 nightly
The price is $561
Jan 4 - Jan 5, 2026
Total with taxes and fees
Chadwick Cove Resort & Marina

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
$923 nightly
The price is $1,004
Jan 9 - Jan 10, 2026
Total with taxes and fees
Gulf View Condominiums

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (346)
"Enjoyable stay. "
United States
Lori
$215 nightly
The price is $242
Jan 5 - Jan 6, 2026
Total with taxes and fees
Tiny House Siesta

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
South Village
9.6 out of 10, Exceptional, (301)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
$466 nightly
The price is $526
Jan 21 - Jan 22, 2026
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
$410 nightly
The price is $464
Dec 28 - Dec 29
Total with taxes and fees
The Inn On Siesta Key

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (79)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
$339 nightly
The price is $383
Jan 4 - Jan 5, 2026
Total with taxes and fees
SeaSpray Resort

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (247)
"Lovely decor, very clean"
United States
Frederick
$146 nightly
The price is $165
Dec 29 - Dec 30
Total with taxes and fees
Kon Tiki Inn

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very Good, (265)
"Amazing place"
United States
Ricardo
$372 nightly
The price is $420
Dec 28 - Dec 29
Total with taxes and fees
Casey Key Resort - Gulf Shores

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)
"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
Siesta Sands Beach Resort Gulf View

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (579)
"Great location, recent updates"
United States
Michael
$184 nightly
The price is $208
Jan 4 - Jan 5, 2026
Total with taxes and fees
A Beach Retreat

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1057)
"Beautiful room. Wonderful staff & views."
United States
Christina
$228 nightly
The price is $255
Dec 25 - Dec 26
Total with taxes and fees
The Suites at Fishermen’s Village- 2 Bedroom Suites

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1177)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
$308 nightly
The price is $349
Jan 4 - Jan 5, 2026
Total with taxes and fees
Siesta Heron Suites & Villas

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (347)
"great location, very clean, quiet"
United States
Joaquin
The Ringling Beach House

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2219)
"Very nice place !"
United States
Ivette
$145 nightly
The price is $163
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5170)
"Great place, easy beach access and property was beautiful. "
United States
Maria
$164 nightly
The price is $185
Jan 4 - Jan 5, 2026
Total with taxes and fees
Tropical Beach Resorts

Heated Pool + Spacious Yard: Port Charlotte Escape

Heated Pool + Spacious Yard: Port Charlotte Escape
3.0 star property
Port Charlotte
$388 nightly
The price is $431
Dec 30 - Dec 31
Total with taxes and fees
Heated Pool + Spacious Yard: Port Charlotte Escape

House of The Sun Siesta Key Crescent Beach

House of The Sun Siesta Key Crescent Beach
4.0 star property
South Village
8.0 out of 10, Very Good, (2)
"The area is beautiful. The condo was very nice. Has everything in it. You can cook if you prefer. The Gulf of Mexico was right behind the condo walk out on to the beach. It also has a pool. I have no complains I would def go back again . "
United States
Margaret Theresa
$706 nightly
The price is $794
Dec 28 - Dec 29
Total with taxes and fees
House of The Sun Siesta Key Crescent Beach

Lulu's Key House Leatherback 2/2 Downstairs

Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
Siesta Key Village
$532 nightly
The price is $598
Dec 27 - Dec 28
Total with taxes and fees
Lulu's Key House Leatherback 2/2 Downstairs

Siesta Sands Beach Resort 4th Floor With Elevator

Siesta Sands Beach Resort 4th Floor With Elevator
3.5 star property
South Village
Siesta Sands Beach Resort 4th Floor With Elevator
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

Price trends for vacation rentals in Englewood

Less expensive
More expensive
Next month
November
March
$231
Month
Price
January
$231
February
$316
March
$383
April
$246
May
$246
June
$236
July
$253
August
$254
September
$211
October
$202
November
$181
December
$222
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Englewood. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Englewood

Everything you need to know about Englewood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Englewood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Englewood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Englewood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Englewood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Englewood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $188 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Englewood rentals

At Expedia, we put the best Englewood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Englewood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Englewood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Englewood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Charming beachside duplex steps to the Gulf with bikes and coastal views: This highly rated vacation home rental in Englewood is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Some other homes for rent in Englewood include ALL NEW-Fully renovated! Steps to beach. Near Boca Grande. Great beaches/fishing and Bohemian Sunrise .

How many vacation rentals are there in Englewood?

Choose from 399 Expedia vacation rentals in Englewood for a memorable vacation.

What can I see and do in Englewood?

Blind Pass Beach and Englewood Beach 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 Stump Pass Beach State Park and Manasota 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.