A blue car with a yellow kayak mounted on its roof.
Photo by Rick Tuers
Open Photo by Rick Tuers

Englewood Vacations from $353

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The Latest Englewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 24 - Sep 28

    Manasota Key Resort + Flight

    Manasota Key
    4 nights
    2.5 star property
    9.4/10 - Exceptional (303 reviews)
    "We LOVED our trip to Manasota Key. Staff was outstanding, room very clean, beach was awesome. Enjoyed every minute. We will be back."
    Reviewed July 10, 2026
    Roundtrip New York (EWR) - Fort Myers (RSW)
    EWR - SRQ1 stop SRQ - EWR1 stop
    Save 100% on your flight
    $1,223
    $736
    per traveler
    found 14 hours ago
    Manasota Key Resort
  • Oct 8 - Oct 11

    LaPlaya Beach & Golf Resort - A Noble House Resort + Flight

    Vanderbilt Beach
    3 nights
    4.5 star property
    9.0/10 - Wonderful (1,001 reviews)
    "I loved everything."
    Reviewed July 16, 2026
    Roundtrip New York (EWR) - Fort Myers (RSW)
    EWR - RSWNonstop RSW - EWRNonstop
    Save 100% on your flight
    $1,423
    $876
    per traveler
    found 1 day ago
    LaPlaya Beach & Golf Resort - A Noble House Resort
  • Oct 6 - Oct 11

    Tween Waters Island Resort & Spa + Flight

    Captiva
    5 nights
    3.0 star property
    8.6/10 - Excellent (1,000 reviews)
    "When looking over the balcony all you see is over grown trees and down below is trash. The elevator was between two buildings and you had to walk to the opposite end just to get to your room. Also the beach is across the street not on the property."
    Reviewed July 14, 2026
    Roundtrip New York (EWR) - Fort Myers (RSW)
    EWR - RSWNonstop RSW - EWRNonstop
    Save 100% on your flight
    $1,247
    $793
    per traveler
    found 1 day ago
    Tween Waters Island Resort & Spa
  • Sep 7 - Sep 12

    A Wave From it All + Flight

    Siesta Isle
    5 nights
    2.0 star property
    Roundtrip Minneapolis (MSP) - Fort Myers (RSW)
    MSP - RSWNonstop RSW - MSPNonstop
    Save 100% on your flight
    $2,265
    $1,459
    per traveler
    found 1 day ago
    A Wave From it All
  • Aug 17 - Aug 22

    Casa Ybel Resort + Flight

    Mid Island
    5 nights
    2.5 star property
    8.8/10 - Excellent (381 reviews)
    "I loved the unit and property. I also like the food and drinks at the restaurant by the pool. I was a little unhappy w housekeeping as they did not clean our room and provide us w clean towels one day."
    Reviewed July 14, 2026
    Roundtrip New York (EWR) - Fort Myers (RSW)
    EWR - MIA1 stop MIA - EWR1 stop
    Save 100% on your flight
    $1,362
    $878
    per traveler
    found 1 day ago
    Casa Ybel Resort

Where to stay in Englewood

Find the best Englewood areas and neighborhoods for the activities you enjoy most. Learn more about Englewood
Learn more about Englewood

Olde Englewood Village

Step back in time at Olde Englewood Village, where historic charm meets Florida's Gulf Coast culture. Stroll along Dearborn Street lined with early 1900s storefronts housing art galleries and antique shops. Discover local history at the Pioneer Museum while enjoying the small-town atmosphere under shady oak trees. The neighborhood offers a genuine slice of coastal Florida without the crowds. Seafood restaurants serve fresh Gulf catch while family-owned cafes welcome locals and visitors alike. Nearby Lemon Bay and community parks provide peaceful retreats after browsing the local craft boutiques and art galleries.

Manasota Beach

If you're spending some time in Manasota Beach, Venice Beach and Manasota Beach are top sights worth seeing.

Manasota

While Manasota might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Manasota Beach and Sarasota National Golf Course.

Englewood Central

While Englewood Central isn't home to many top sights, Lemon Bay Playhouse and Englewood South Inlet are some notable places to visit nearby.

Grove City

While Grove City might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Stump Pass Beach State Park and Englewood Beach.

Discover the most popular places to visit in Englewood

What to do in Englewood

Englewood Hotel Deals

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.

Frequently Asked Questions

How much does an Englewood vacation package cost?

Offering great value package deals from $736 on Expedia, you'll be thrilled with how little a vacation to Englewood costs! Our packages make travel planning easier and your savings go further.

What are the cheapest months to go to Englewood?

July, September and October are great times to search for cheap Englewood vacation packages. Traveling in quieter months means you can usually find lower prices on flights and hotels.

How many days is enough for Englewood?

With around 3 days, you'll have enough time to visit popular neighborhoods such as Clintwood Acres and Bay Harbor Estates during your Englewood vacation. Be sure to also add Stump Pass Beach State Park and Lemon Bay Playhouse to your must-do list. Up for some more adventures? Consider exploring outside of Englewood on day trips and tours.

Is it worth booking a vacation package to Englewood?

Englewood has everything you need for a wonderful escape. Get your Englewood vacation off to a flying start by visiting major attractions like Englewood Beach.

How to find the best Englewood package deals?

Use Expedia's handy filters to find some tempting Englewood package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Englewood package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.

Is it cheaper to book an Englewood vacation as a package?

Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Englewood vacation by choosing your favorite airline, accommodation type and car class.

When to book a vacation package to Englewood?

If you're considering an impromptu Englewood adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking well in advance.

How to plan a trip to Englewood?

  1. Pick your dates: The things you plan to do in Englewood and your favorite season can help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and food to experiences and flights. Your hotel will likely be the biggest expense during your trip to Englewood.
  3. Use Expedia's trip planning tool to discover Englewood: Research every aspect of your trip to Englewood with this handy planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Set the duration of your trip: Start by making a list of all the attractions and activities you want to get to in Englewood. Then, estimate how long you'll need at each, along with any travel time.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose an Englewood vacation package that brings all your bookings together.
  6. Add on excursions and experiences: Take a look at our dedicated travel guide to find some awesome things to do in Englewood. Book tickets or make reservations in advance to save time and avoid the hassle of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Englewood vacation packages?

Your Englewood trip should be an escape from your daily routine, not a reason for money-related stress. So to give you a little more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

Book with confidence

Things to do in and around Englewood

Englewood, Florida, is perfect for beach and outdoor enthusiasts seeking scenic vacations. Visitors can explore recreational areas, enjoy golf at local courses, and take advantage of the stunning beaches. Essential information includes a beach guide, outdoor recreation options, and suggestions for day trips to enhance your experience in this charming coastal town.

Shopping

For a great shopping experience in Englewood, check out the local options like the Sun Flea Market, offering a variety of goods and city vibes. If you're up for a drive, visit the Port Charlotte Town Center and Fishermen's Village for more entertainment and family-friendly shopping.

Recreation

Experience a round of golf at Sarasota National Golf Course, where you can enjoy the outdoors and the sport in a beautiful setting, just 5 miles from Englewood. For relaxation, visit the Englewood Recreation Center to unwind and rejuvenate in a serene atmosphere.

Adventure

At the North Port Aquatic Center, 11 miles from Englewood, dive into thrilling water slides and wave pools, perfect for family fun. For a dose of activity, visit the Morgan Family Community Center, also 11 miles away, offering various engaging programs. Treasure Lanes, 13 miles away, promises arcade excitement for all ages.

Nightlife

Englewood offers a relaxed nightlife vibe. Enjoy live music at the local tiki bars, or unwind with a drink at the charming waterfront pubs. For a taste of local flavor, check out the cozy restaurants that often feature evening entertainment. The atmosphere is welcoming and laid-back.

Find the best attractions in and around Englewood

Englewood, Florida, is perfect for a beach and outdoor vacation, offering a variety of attractions like Englewood Beach, Manasota Beach, and urban parks. Visitors can enjoy stunning scenery and family-friendly experiences with easy beach access and some of the best beaches in the area. Explore the local preserves and enjoy the natural beauty that Englewood has to offer for an unforgettable getaway.

  • Englewood Beach: Enjoy the stunning sunsets and soft sands of Englewood Beach, perfect for relaxing days under the sun. With its inviting beach vibes, it’s an ideal spot for sunbathing, swimming, and beachcombing.
  • Lemon Bay Park: This urban park offers a blend of family-friendly outdoor activities amidst beautiful nature trails and wildlife. It’s perfect for picnics, hiking, and enjoying the serene environment right in the heart of Englewood.
  • Venice Fishing Pier: Located just 9 miles from Englewood, this family-friendly pier is great for fishing, strolling, and taking in breathtaking ocean views. It’s a perfect spot to experience the local marine life and enjoy the coastal atmosphere.

Best time to go to Englewood

The best time to visit Englewood can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Englewood falls in August, when visitor numbers are slightly low and weather is mostly sunny with light rain. The coolest average temperature in Englewood falls in January, visitor numbers are average and weather is mostly sunny with no rain.

Tips to save on your trip to Englewood

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Englewood.
  • Consider traveling to Englewood during the low season (August to September and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.