Holiday rentals in Englewood

New! Lemon Bay•Hot Tub•Sunsets•Pontoon Rentals!

Plan a winter warm-up on scenic Lemon Bay in Englewood, Florida! This waterfront retreat blends relaxation and adventure. Enjoy gorgeous sunset views while soaking in the hot tub, and watch dolphins play in the bay. Rent the pontoon and explore the water, offering easy access to beaches and fishing. Stump Pass is just across the bay! This 3000 sq. ft. newly remodeled home has plenty of space for your group to enjoy comfortably. Book now for a peaceful Gulf Coast getaway with unforgettable views.

Lemon Bay Canal Home – Pool, Hot Tub & Boat Dock

Welcome to your private escape nestled on a secluded peninsula in Lemon Bay, just minutes from the Gulf of Mexico. This 2-bedroom, 3-bathroom pool home is a boater’s dream with direct canal access to open water—no bridges, no height restrictions. Just tie up at your private dock and you’re off to explore Lemon Bay, Stump Pass, and the Gulf in no time. Whether you’re into fishing, beachcombing, or simply relaxing poolside, this home offers the perfect blend of privacy, comfort, and location.

1mi to Beach. 1+ acre of jungle Pool & Pickleball

Over 1.2 acres of scenic Florida landscape to explore. Home to 50+ different plants, birds, animals and walking trails you are sure to feel like you are in a jungle oasis. Just 1 mile to Manasota Beach the shark tooth capital of the world! Explore all the beach has to offer with a 3-4min car/bike ride. The house has a huge lanai with pool, tv and seating areas. Two bedrooms and 1 bathroom with a tub. Just ten 5 min away 20+ restaurants and grocery stores. Escape the noise and enjoy nature.

Walk to beach~Sleeps 6 (B1)

This updated 1,400 s/f vacation home with vaulted ceilings is a great place to relax after a day at the beach. (Your private access to the beach is directly across the street!) Large master suite and guest bedroom with large deck. Fully appointed kitchen/dining with adjoining screened lanai. Complete with all the comforts of home. Please see "other details to note" for a description of your private beach access to enjoy sunny days and superb sunsets over the Gulf of Mexico.

Green Bamboo - saltwater pool, great backyard.

Welcome to Green Bamboo, the charming and cozy vacation rental located in the beautiful Englewood, Florida! With its prime location, Green Bamboo is the perfect place to explore all that the area has to offer, from the most amazing beaches in the US to world-class golf courses and spectacular sunsets. Home is situated in a peaceful and gorgeous neighborhood. Just a short drive away (5 miles) you will find beautiful beaches, boat rentals and vibrant shopping and dining options.

Island Condo Sun & Fun, Deeded Beach (Suite 4)

COMPLETELY UPDATED AFTER STORM. Welcome to salty air getaway on the beautiful Florida west coast. This charming one-bedroom, one-bath retreat offers the ideal blend of comfort and coastal charm. Located on Manasota Key you will enjoy your morning coffee on the private balcony with stunning ocean breeze as salt is in the air. you'll find a cozy living area, a fully equipped kitchen, and a serene bedroom with plush linens. Just a 5 min walk to the sandy shores. Book today!

Peaceful waterfront home

Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in our cocktail pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

Private Beach-Luxury 4BR+SUPs&Kayaks-Pets-BBQ

Charming 4 Bed Cottage (sleeps 9), Private Beach to Gulf Across Street, with Large Screened Porch, Super Shark Tooth Hunting, Free use of 2 Kayaks and SUPs, Restaurants, Live Music, Golf, and Tennis . Uber Eats & Grocery delivery, 50 Minutes from Sarasota Airport (75 minutes from Fort Myers airport). Lush tropical rainforest in the "Old Florida" region on the Gulf surrounds this cute cottage. *Please note small extra $50 pp nightly fee for guests 7-9.

Manasota Key

Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.

Mermaid House on Wilhelm A- Manasota Key, FL

The Mermaid House on Wilhelm survived Milton and is still a wonderful getaway on Manasota Key. Just 120 steps to the beach with everything you need to make your stay perfect. Get the privacy of Manasota and a variety of nightlife close by on the island. The entire upper is yours with this rental. The house has a full kitchen, Smart TVs and 1 gig internet. Sit on the porch, enjoy a glass on wine and the perfect view of the gulf.

Modern Family-Friendly Home Near Englewood Beach

Discover your perfect vacation getaway in this spacious and modern 3-bedroom, 2-bathroom home, just minutes away from the beautiful Englewood Beach. Whether you're looking to unwind or have an adventure, this home is designed to comfortably accommodate families or large groups, offering both relaxation and fun for everyone.

The Manor House on Lemon Bay. Available April 6th!

The Manor House on Lemon Bay will be your escape from reality as you relax and enjoy the laid back waterfront atmosphere at Tiki on the Bay. This small, inviting community is perfectly located. You're just moments from multiple Gulf front beaches, Historic Dearborn Street, and fantastic restaurants.