Vacation rentals in Englewood

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Top-rated vacation rentals in Englewood

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Top guest favorite
A spacious bathroom showcases a freestanding bathtub beside a large mirror with stylish lighting. Natural light filters through two windows adorned with sheer curtains. A modern sink area with sleek cabinetry complements the light grey walls, providing an airy and relaxing atmosphere.
Villa in Englewood
4.98 out of 5 average rating, 102 reviews

Coastal Retreat Villa with pool • near beaches

🌴 Escape to your getaway in sunny Englewood, Florida! Whether you're a couple seeking romance, a solo adventurer, a business traveler, or a family with kids, our home is designed for comfort & relaxation. Nestled in a prime location, it's the ideal home base to anyone looking to unwind and explore. Indulge yourself in this executive cozy, built from the ground in 2018 & featuring 3 bedrooms, 2,5-bath house with a Large (seasonally) heated swimming Pool (heating $ included during colder months)

Guest favorite
A tranquil pool reflects a colorful sunset with hues of orange and pink in the sky, surrounded by lush greenery. The paved area features decorative stonework, enhancing the serene outdoor setting by the Gulf of Mexico.
Guesthouse in Englewood
4.91 out of 5 average rating, 275 reviews

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

Guest favorite
A view from the porch captures a vibrant sunset over the Gulf of Mexico, with silhouettes of palm trees and nearby buildings. The warm colors of the sky blend into the horizon, creating a serene backdrop that enhances the coastal atmosphere.
Condo in Englewood
4.93 out of 5 average rating, 152 reviews

Gulf Side Condo Englewood Florida

Monthly bookings will receive a 15% discount at this cozy 2 bed 2 bath condo. The condo has a full kitchen, dining area, living room, a king size master bedroom and a small 2nd bedroom. The coastal decor and furnishings create the ambiance of an island home. The condo opens onto a wide porch which has beautiful views of the Gulf of Mexico. Wander down the sandy path to a private beach and the turquoise waters of the Gulf. Enjoy Gulf breezes and sunsets from the porch or the beach.

Guest favorite
An aerial view captures the coastline of Manasota Key, showcasing the blue-green waters and sandy beach. The surrounding area features a mix of residential buildings and green spaces, with multiple boats visible in the water and a bridge connecting to nearby islands.
Cottage in Englewood
4.9 out of 5 average rating, 155 reviews

Free kayak/bikes/walk to beach/full cottage #1

Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

Top guest favorite
An aerial view showcases a raised townhome surrounded by palm trees, with the beach and ocean visible in the background. The home's light blue exterior complements the coastal setting, while a spacious deck on the lower level offers an inviting space for relaxation.
Townhouse in Englewood
4.96 out of 5 average rating, 135 reviews

Amazing Sunsets just 50 steps to uncrowded beach

Escape to your dream coastal retreat! This exquisite 2- king bedroom, 2-bathroom home is a paradise, located just steps from the beach. Nestled among swaying palm trees, this haven offers a serene oasis where the calming sounds of the water create a tranquil atmosphere for you and your loved ones. Live among palm trees, with the ocean as your neighbor and the sand as your playground. Natural light floods the modern interior through the large windows creating a warm and inviting atmosphere.

Top guest favorite
The exterior of a spacious home features a light-colored facade framed by lush, mature palm trees. A manicured lawn extends in front, and large windows offer a glimpse of the inviting interior. The roof exhibits a gentle slope, contributing to the overall elegance of the residence.
Home in Englewood
4.84 out of 5 average rating, 211 reviews

Manasota Beach Home w/heated pool walk to beach

Custom built large home only 2 blocks to Manasota Beach. Most guests walk and a beach wagon is provided. Located in a quiet neighborhood with easy access to downtown Venice and Englewood. Very large and private lot with beautiful mature palms! The home has tray and soaring vaulted ceilings. The whole home opens up onto the pool area with sliders in every room. The bedrooms are configured in a split style with the very large master suite being totally private. Rare beach home for rent left!

Top guest favorite
A spacious patio area is showcased, featuring a comfortable sectional sofa adorned with colorful pillows. A coffee table is positioned in front, while the heated pool and a wooden pergola are visible through large screened windows, enhancing the outdoor experience.
Home in Englewood
4.99 out of 5 average rating, 107 reviews

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.

Top guest favorite
A cozy sleeping area features a spacious bed with light-colored bedding and decorative pillows. An ornate mirror and a television are positioned on a fireplace mantel. Warm light filters through sheer curtains, illuminating the inviting space decorated with tasteful artwork.
Apartment in Englewood
4.97 out of 5 average rating, 292 reviews

The Oz Tree House over looking Hot tub, Pool

The Tree house apartment has its own entrance and off street parking. Two blocks from Dearborn St. and 2.9 miles to the beach. Light and airy in a private setting with gardens, hammock, fire pit a quiet and peaceful, walking distance to everything the historic district of Old Englewood has to offer. Public tennis courts, great restaurants with live music and once a week a fantastic Farmers Market comes to town! Lemon Bay and Indian Mound are a nice walk to enjoy the sunsets

Guest favorite
A front porch is framed by pink hibiscus flowers and lush greenery. Rocking chairs are positioned along the porch, with a view of a well-kept garden and trees in the background. The overall atmosphere reflects a serene outdoor space.
Guest suite in Englewood
4.98 out of 5 average rating, 209 reviews

Blue Cottage Suite- Peaceful Old Englewood Charm!

This charming rental is in historic Old Englewood right at the edge of Lemon Bay. The Blue Cottage is in a quiet neighborhood just 4 blocks from Dearborn Avenue with all great entertainment, eclectic shopping and restaurants, live music, and more. The Front porch pictured is part of the main house and is NOT included for use while renting the Blue Cottage Suite. IF the main home is vacant during your stay, I will let you know and it can be used during that time.

Guest favorite
Home in Englewood
4.92 out of 5 average rating, 151 reviews

Island Home & Casita, Pool, Golf Cart, Beach

Complimentary golf cart INCLUDED. With a short stroll to warm sand and crystal waters of Englewood Beach. With all the the modern comforts in place all you have to do is relax on your short stay or extended visit. Updated 2/2 main house and 1/1 Casita with a private entrance. Walk right out the front door to the new expansive pool patio featuring a saltwater heated pool, outdoor kitchen and plenty of furniture for spending time soaking in the warm Florida sun!

Guest favorite
A beachfront property is depicted, featuring a two-story structure with a spacious porch. Surrounding landscape includes sand and lush greenery, leading to the waves of the Gulf of Mexico. Sunbathers are seen in the distance, enjoying the beach atmosphere.
Condo in Englewood
4.91 out of 5 average rating, 202 reviews

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.

Top guest favorite
An entrance is framed by lush palm trees and tropical foliage. A concrete path leads to a door, showcasing a welcoming façade with a single window providing natural light.
Guesthouse in Englewood
4.92 out of 5 average rating, 229 reviews

1 bed apart/full kitchen 5 min. drive to the Beach

Ready to relax at the beach with a cold drink? Englewood FL. has 3 nice beaches to choose from. Venice has nice shopping and lots of sharks teeth.This nice apt. is ideal for those that want to go to the beaches and look for sharks teeth,eat great local food and enjoy the beautiful Southwest Florida weather.The Wi-Fi is not the best but should run Netflix. A percent of our earnings goes to a few international charities

Popular amenities for Englewood vacation rentals

Quick stats about vacation rentals in Englewood

  • Total rentals

    1K properties

  • Nightly prices starting at

    R695 ZAR before taxes and fees

  • Total number of reviews

    25K reviews

  • Family-friendly rentals

    810 properties are a good fit for families

  • Pet-friendly rentals

    370 properties allow pets

  • Rentals with a pool

    520 properties have a pool

Your guide to Englewood

Introduction

Located an hour’s drive south of Sarasota on Lemon Bay, Englewood is known for its mellow beaches, birding, and any and every activity related to being on the water. On the mainland lies Old Englewood Village, a classic old Florida main street with pastel cottages and sidewalk cafes, while over the bridge, you’ll find the white-sand beaches of Manasota Key. These barrier islands and the surrounding area are riven with waterways just begging to be explored by kayak or canoe. Cast a line to catch a snook and bring your binoculars to spot an osprey, or, if you’re lucky, catch a glimpse of the elusive manatee. In the summer, loggerhead turtles nest on the island. Should you tire of the waterfront, there’s plenty more to do in the area: hit the golf course, visit the mineral springs in North Port, catch a spring training baseball game at Port Charlotte, or drive past the curious planned community of Rotonda West.


The best time to stay in a vacation rental in Englewood

As the tourist brochure likes to say, it’s always summer in Sarasota County. Most people prefer to book vacation rentals here for the fall, winter, and spring, when temperatures are almost always in the 70s Fahrenheit and Gulf breezes bring maximum comfort. In the actual summer, though, the region is less than ideal, weatherwise. It can be rainy and hot, with temperatures in the 90s, not to mention humid and buggy. The water temperature is good for swimming all year round, rarely dropping below 68 degrees.


Top things to do in Englewood

Beaches

Just across the bridge from historic downtown Englewood, Manasota Key is home to some of the Sarasota area’s least crowded beaches. You can go for a birding walk through secluded Stump Pass Beach, looking out for frigate birds as well as gopher tortoises and manatees, or hunt for shells and shark teeth at low tide on the busier Englewood Beach.

Lemon Bay Aquatic Preserve

Waters from seven tributaries converge in this long, shallow bay that separates downtown Englewood from Manasota Key. Surrounded by seagrass, marsh, and mangroves, this biodiverse ecosystem supports some 150 bird species and 200 species of fish. You can charter an eco-tour or explore on your own with a rental kayak.

Little Gasparilla Island and Don Pedro Island State Park

These adjacent islands offer miles of beachfront to explore, as well as the sand dunes and mangrove forests of Don Pedro Island, a 230-acre state park that’s accessible only by ferry boat. Don’t forget your rod and reel, swimsuit, and SPF — and watch out for nesting sea turtles.

Frequently Asked Questions

  • Where should I stay in Englewood?

    Make yourself at home in Englewood by choosing from our most frequently booked neighborhoods. We have over 190 vacation rentals in Englewood Isles, and over 1,000 vacation rentals in Old Englewood Village.

  • Are there vacation rentals with a dedicated workspace in Englewood?

    Yes! Work meets play with ease at over 430 vacation rentals in Englewood featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Englewood?

    Four-legged friends are welcome in Englewood. Choose from more than 370 vacation rentals for guests traveling with pets.

  • Are there Englewood vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 500 vacation homes with pools in Englewood, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in condo rentals in Englewood?

    Experience the best of Englewood with our condo rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Englewood have a gym?

    Absolutely! We offer over 20 house rentals with a gym in Englewood. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Englewood have a bbq area?

    Absolutely! We offer over 60 condo rentals with a bbq area in Englewood. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Englewood have self check-in?

    Absolutely! We offer over 20 cottage rentals with self check-in in Englewood. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly townhouse rentals in Englewood?

    Englewood has more than 10 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Englewood?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a gym, over 110 homes with self check-in, over 160 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Englewood