New listingEnglewood
Vacation Rentals
Book direct & save up to 20%
Once known primarily for its fishing industry, Englewood has evolved into a vibrant and multifaceted destination. Its thriving arts scene and authentic beach town charm attract visitors from all walks of life.
With sun-kissed beaches, powdery white sands, and a wide range of water-based activities, Englewood is an undisputed gem along the Gulf of Mexico.
Search Englewood vacation rentals
We can't find anything online to match your search requirements, but why not call the team on (941) 681 2002 and let us find the perfect vacation rental for you!
Don't forget to reset the search bar to view all properties.
Don't forget to reset the search bar to view all properties.
New listingPool AccessBeach Access
New listingSandpiper Key 2BR Bay Views & Heated Pools
From $700 per week
New listingPet Friendly Canal Home - Boat Lift + Paddleboards
From $1,330 per week
New listing3BR Pool & Hot Tub Villa in Rotonda West
From $1,400 per week
Venice Villas San Marco Golden Beach
From $1,120 per week
Golf Retreat - Pool, Spa & Fire Pit
From $980 per week
Englewood is made up of a mix of waterfront and inland neighborhoods, each with its own unique character.
Notable areas include Olde Englewood, Manasota Key, East Englewood, five communities within Rotonda West, Placida, Grove City, Cape Haze, Gulf Cove/South Gulf Cove, Little Gasparilla Island, Knight Island (also known as Palm Island), and Boca Grande. This scenic community spans both Sarasota and Charlotte counties.
What makes Englewood special is its stunning Gulf views, diverse water sports, charming shops, and a rich cultural calendar that draws visitors year-round.
For the thrill-seeker, parasailing over the Gulf offers an unforgettable experience, while outdoor enthusiasts can explore numerous biking and hiking trails. The area is also home to 11 beautiful golf courses, most of which are open to the public year-round. Sport fishing remains a major draw, with options ranging from backwater flats fishing to world-class Tarpon fishing. Englewood also boasts the Lemon Bay Playhouse on historic Dearborn Street, where live community theater takes place year-round. Dining options are plentiful, with many restaurants offering fresh Florida seafood and delicious southern cuisine.
Unquestionably, the main attraction in Englewood is its pristine beaches and waterways. Manasota Key features four stunning beaches, all accessible via two bridges: Tom Adams Bridge and Manasota Beach Road Bridge.
Visitors can enjoy the Gulf’s tranquil beauty at Englewood Beach, Manasota Beach, Stump Pass Beach, or Blind Pass Beach. Each beach is preserved and protected by the state of Florida, ensuring that the white sands and natural habitats remain pristine throughout the year. From May to October, lucky visitors may witness sea turtles nesting or watch playful dolphins in the surf.
Englewood is also home to several scenic parks, such as Ann Dever Memorial Regional Park, Lemon Bay Park and Nature Center, and Cedar Point Environmental Park. Many of these parks offer opportunities for canoeing, kayaking, fishing, and wildlife viewing in natural preserves.
With its low-rise buildings and peaceful atmosphere, Englewood offers a serene, unhurried escape where visitors can make lasting memories. There’s always something to explore, whether you’re drawn to its natural beauty, outdoor adventures, or cultural experiences.
Curated Southwest Florida stays
Find your place on Florida’s Gulf Coast
Explore locally managed Florida Gulf Coast vacation rentals in the places our team knows best. Compare beach escapes, waterfront homes and spacious pool stays, then book direct for local support and exceptional value.
- Book direct & save up to 20%
- Locally managed
- Guest support before and during your stay
01Beach & bay
Englewood
Unhurried beach days, boating on Lemon Bay and welcoming coastal neighborhoods.
02Island life
Manasota Key
Gulf sunsets, Lemon Bay adventures and relaxed island homes close to the water.
03Iconic coast
Siesta Key
Powder-soft sand, island dining and memorable stays beside the Gulf.
04Historic coast
Venice
Charming downtown streets, a celebrated pier and easygoing Gulf beaches.
05Modern Florida
Wellen Park
Lakefront dining, live events, recreation trails and modern vacation homes.
06Southwest Florida
Fort Myers & Bonita Beach
White-sand beaches, Lovers Key nature and waterfront days around Estero Bay.
07Harbor living
Punta Gorda & Charlotte Harbor
Waterfront neighborhoods, boating access and a relaxed harbor-side rhythm.
Make it yours
Start with what makes your stay perfect
Beach at your doorstep, a private pool or room for the whole family—choose what matters and jump straight into matching Gulf Coast vacation rentals.