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Check prices for these dates

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21 Dec - 22 Dec
Tomorrow
22 Dec - 23 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Our top choices for Englewood holiday rentals

Exterior
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 4.624.861 ₫
17.021.594 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Chadwick Cove Resort & Marina
Luxury Condo, Beach View | Balcony
Gulf View Condominiums

Condo in Manasota Key

Gulf View Condominiums
3.5 star property
The price is 10.657.575 ₫
26.409.735 ₫ 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 2.231.512 ₫
5.719.039 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Tiny House Siesta
Property grounds
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, (301)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is 10.420.740 ₫
13.113.554 ₫ total
includes taxes & fees
21 Jan - 22 Jan 2026
The Residences at Siesta Key Beach by Hyatt Vacation Club
Beach nearby, white sand, beach umbrellas, beach towels
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 7.432.672 ₫
9.855.982 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Inn On Siesta Key
Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi
SeaSpray Resort

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (79)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
The price is 8.131.335 ₫
9.188.409 ₫ total
includes taxes & fees
22 Dec - 23 Dec
SeaSpray Resort
Terrace/patio
Kon Tiki Inn

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (247)
"Lovely decor, very clean"
United States
Frederick
The price is 6.155.342 ₫
6.955.537 ₫ total
includes taxes & fees
20 Jan - 21 Jan 2026
Kon Tiki Inn
Outdoor wedding area
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, (265)
"Amazing place"
United States
Ricardo
Casey Key Resort - Gulf Shores
Condo (Siesta Sands Beach Resort Gulf View) | Exterior
Siesta Sands Beach Resort Gulf View

Condo in South Village

Siesta Sands Beach Resort Gulf View
2.5 star property
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
The price is 6.106.396 ₫
16.367.406 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Siesta Sands Beach Resort Gulf View
Beachside One Bedroom Suite | Premium bedding, pillow-top beds, individually decorated
A Beach Retreat

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (577)
"Great location, recent updates"
United States
Michael
A Beach Retreat
Village Beach & Harbor Suite | Balcony view
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, (1052)
"Clean room, beautiful area, excellent staff"
United States
Crystal
The price is 4.966.430 ₫
5.562.465 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Suites at Fishermen’s Village- 2 Bedroom Suites
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, (1175)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services
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 4.895.379 ₫
10.824.778 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Heron Suites & Villas
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, (346)
"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, (2215)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key
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, (5162)
"Great place, easy beach access and property was beautiful. "
United States
Maria
The price is 3.332.795 ₫
4.360.777 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Tropical Beach Resorts
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 3.052.540 ₫
11.353.870 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Heated Pool + Spacious Yard: Port Charlotte Escape
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
The price is 11.032.564 ₫
23.319.563 ₫ total
includes taxes & fees
28 Dec - 29 Dec
House of The Sun Siesta Key Crescent Beach
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
The price is 7.748.452 ₫
16.851.075 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Lulu's Key House Leatherback 2/2 Downstairs
Condo (Siesta Sands Beach Resort 4th Floor w) | Exterior
Siesta Sands Beach Resort 4th Floor With Elevator

Condo in South Village

Siesta Sands Beach Resort 4th Floor With Elevator
3.5 star property
The price is 5.559.044 ₫
16.305.302 ₫ total
includes taxes & fees
24 Dec - 25 Dec
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

Paradise Cove at Lemon Bay

Paradise Cove at Lemon Bay

10/10 Excellent
"Amazing little gem."
Amanda 3-night trip
Posted 8 days ago
Paradise Cove at Lemon Bay

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 399 Expedia holiday rentals in Englewood for a memorable holiday.

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 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.