Photo by peter spagnuolo

Search Holiday Rentals in Englewood

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Englewood holiday rentals

Property grounds
Chadwick Cove Resort & Marina

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
The price is ฿2,518
฿17,107 total
includes taxes & fees
16 Dec - 17 Dec
Chadwick Cove Resort & Marina
Exterior
Gulf View Condominiums

Condo in Manasota Key

Gulf View Condominiums
3.5 star property
The price is ฿14,202
฿33,368 total
includes taxes & fees
9 Jan - 10 Jan 2026
Gulf View Condominiums
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services
Tiny House Siesta

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (346)
"Enjoyable stay. "
United States
Lori
The price is ฿3,397
฿7,697 total
includes taxes & fees
13 Dec - 14 Dec
Tiny House Siesta
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in South Village

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (299)
"Great spacious room with updated amenities as well as a great white beach and amazing staff! "
United States
Rebecca
The price is ฿12,631
฿15,882 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Inn On Siesta Key

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is ฿16,042
฿20,100 total
includes taxes & fees
28 Dec - 29 Dec
The Inn On Siesta Key
Outdoor pool
The Suites at Fishermen’s Village- 2 Bedroom Suites

Condo resort in Punta Gorda Isles

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (1044)
"Clean room, beautiful area, excellent staff"
United States
Crystal
The price is ฿5,478
฿6,135 total
includes taxes & fees
14 Dec - 15 Dec
The Suites at Fishermen’s Village- 2 Bedroom Suites
Deluxe Studio, Bay View | View from room
Casey Key Resort - Gulf Shores

Apartment in Casey Key

Casey Key Resort - Gulf Shores
3.0 star property
8.4 out of 10, Very good, (264)
"Amazing place"
United States
Ricardo
Casey Key Resort - Gulf Shores
Deluxe Suite, 2 Bedrooms | Living area | TV
SeaSpray Resort

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (76)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
The price is ฿6,318
฿7,140 total
includes taxes & fees
14 Dec - 15 Dec
SeaSpray Resort
Condo (House of Sun Siesta Key Crescent Beac) | Exterior
House of The Sun Siesta Key Crescent Beach

Condo in South Village

House of The Sun Siesta Key Crescent Beach
4.0 star property
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
House of The Sun Siesta Key Crescent Beach
Exterior
Kon Tiki Inn

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (246)
"Staff was great, room was clean and comfortable. It was a short stay but we enjoyed our time there. We will be back!"
United States
Joan
The price is ฿5,144
฿5,812 total
includes taxes & fees
15 Dec - 16 Dec
Kon Tiki Inn
Exterior
Siesta Key Island Rentals

Holiday Home in Siesta Key

Siesta Key Island Rentals
3.0 star property
9.6 out of 10, Exceptional, (53)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
The price is ฿3,688
฿8,861 total
includes taxes & fees
15 Dec - 16 Dec
Siesta Key Island Rentals
On the beach, white sand
A Beach Retreat

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (576)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
A Beach Retreat
House (2 Bedrooms) | Interior
Relax in Hot Tub, Walk to Springs: North Port Home

Cottage in North Port

Relax in Hot Tub, Walk to Springs: North Port Home
3.0 star property
The price is ฿2,310
฿7,093 total
includes taxes & fees
15 Dec - 16 Dec
Relax in Hot Tub, Walk to Springs: North Port Home
Condo, Pool View | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Siesta Heron Suites & Villas

Holiday Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is ฿5,469
฿12,566 total
includes taxes & fees
21 Dec - 22 Dec
Siesta Heron Suites & Villas
Front of property – evening/night
Captiva Beach Resort

Condo in South Village

Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1171)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas
Tropical Beach Resorts

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5144)
"Great place, easy beach access and property was beautiful. "
United States
Maria
The price is ฿4,021
฿5,262 total
includes taxes & fees
14 Dec - 15 Dec
Tropical Beach Resorts
Front of property
The Ringling Beach House

Apartment in Siesta Key

The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (344)
"great location, very clean, quiet"
United States
Joaquin
The Ringling Beach House
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers
Hibiscus Suites - Gateway to Siesta Key

Aparthotel in Sarasota

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2210)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key
Condo (LuLu's Key House Leatherback 2/2 Down) | Exterior
Lulu's Key House Leatherback 2/2 Downstairs

Holiday Home in Siesta Key Village

Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
Lulu's Key House Leatherback 2/2 Downstairs
House (3 Bedrooms) | Interior
Heated Pool + Spacious Yard: Port Charlotte Escape

Cottage in Port Charlotte

Heated Pool + Spacious Yard: Port Charlotte Escape
3.0 star property
The price is ฿3,683
฿13,699 total
includes taxes & fees
13 Dec - 14 Dec
Heated Pool + Spacious Yard: Port Charlotte Escape
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Englewood Hotel Reviews

Sun Coast Inn

Sun Coast Inn

10/10 Excellent
"Clean room, welcoming staff, great air conditioning, covered parking, quiet room and lots of towels. Two excellent restaurants within 100 yards. Match all this with a room rate that can't be beat and I think you'll agree this property is unmatched in this area. Will definitely stay here again "
frank 1-night trip
Posted 6 days ago
Sun Coast Inn

Find out more about Englewood

Search for holiday rentals in Englewood on Expedia! You can easily find your home rentals, villas, holiday apartments in Englewood using one of the methods below:

  • View our selection of featured holiday rentals in Englewood
  • Use the map to find apartments and other holiday homes in the Englewood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Englewood while they last

Look no further and take a look at our great range of rental properties in Englewood!

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.

How many holiday rentals are there in Englewood?

Choose from 401 Expedia holiday rentals in Englewood for a memorable holiday.

What can I see and do in Englewood?

Blind Pass Beach and Lemon Bay Park 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 Englewood Beach and Stump Pass Beach State Park.

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.