Holiday rentals in Englewood

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Top-rated holiday rentals in Englewood

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Guest suite in Port Charlotte
4.96 out of 5 average rating, 131 reviews

Garage to a Tiny House Studio Near Shopping Center

Experience comfort and style in this charming, pet-friendly space, perfect for short getaways. Enjoy the privacy of your own entrance, along with a full shower, cozy living room, dining area, and bedroom, all within one convenient layout. The fully fenced backyard, shared with other tenants, features a grill and fire pit—ideal for relaxing evenings outdoors. While the space includes a kitchenette, access to the main shared house may be available if you need a full kitchen or laundry facilities.

Top guest favourite
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, 141 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 favourite
A charming yellow house is embraced by tall palm trees and lush greenery. A welcoming entrance features a black wrought iron gate framed by vibrant tropical plants. Light cascades from the windows, reflecting the historic character of the home.
Flat in Port Charlotte
4.94 out of 5 average rating, 115 reviews

Old Florida Charm near Beaches

Take it easy at this unique and tranquil getaway. Florida charm at its finest. Tropical garden setting in an historic home in your own private space. Walking distance to three restaurants including an original landmark restaurant, the Bean Depot. Fishing pier and boat ramp on the Myakka River to the gulf are also nearby. The house was originally owned by the Adams Family, makers of chewing gum ( chicklets and tea berry gum). Beautifully restored older home with lush tropical landscaping.

Top guest favourite
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, 210 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.

Top guest favourite
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.
Apartment in Englewood
4.91 out of 5 average rating, 211 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 favourite
A spacious interior of a cozy tiny house studio is featured, showcasing a comfortable king-size bed and a small dining table. A well-equipped kitchen area with modern appliances and a rustic wooden countertop is visible, along with light streaming in through bright windows.
Guest suite in North Port
4.93 out of 5 average rating, 115 reviews

Charming Studio w/ King Bed near Mineral Springs

Escape to our cozy Tiny House Studio in North Port, FL, just minutes from the relaxing Warm Mineral Springs! This charming garage conversion offers a private entrance, a comfortable king-size bed, and a full bathroom. With its own in-unit laundry and a small kitchen, you'll have everything you need for a convenient and relaxing stay. Perfect for those seeking a peaceful retreat close to local attractions, this studio is your ideal getaway!

Top guest favourite
Apartment in Englewood
4.97 out of 5 average rating, 105 reviews

Studio, pool, private beach, boat dock shark teeth

Enjoy it all -Pool, private dock & private beach access-located near restaurants. Covered parking or hop on a shuttle to explore Manasota Key! Light, bright condo is complete with everything you will need to relax. Kitchenette has all the must haves-air fryer, portable stove, coffee maker, kettle & community grill. Enjoy a queen bed, shower and community washer/dryer. Fish off the pier, reserve a dock or check out the private beach.

Top guest favourite
A comfortable bedroom features a spacious bed with crisp white linens, accented by decorative pillows. Two framed beach-themed images hang on the blue wall, and natural light filters through a nearby window, complemented by light, airy curtains.
Guest house in Venice
4.92 out of 5 average rating, 187 reviews

Private, cozy, beach guest-suite

Discover your slice of paradise in Venice, Florida! Our charming Airbnb apartment offers a cozy and comfortable retreat in this coastal gem. With a great location, this apartment is your gateway to pristine beaches, local culture, and vibrant dining options. Perfect for a relaxing getaway, this apartment invites you to explore all that Venice has to offer. Book your stay today and experience the magic of Venice, Florida.

Top guest favourite
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.
Guest house in Englewood
4.92 out of 5 average rating, 234 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

Top guest favourite
The living area features a comfortable sofa adorned with decorative pillows and a woven chair. Natural light filters through a large window, enhancing the space. A wooden coffee table sits in the center, with a decorative bowl and greenery on display, while soft curtains frame the window.
Guest house in Englewood
4.98 out of 5 average rating, 123 reviews

Blue Bungalow-Quaint & Quiet-Perfect Getaway!

Looking for something extraordinary? This charming, full, one bedroom upscale bungalow is in Historic Old Englewood, overlooking an inlet of Lemon Bay. Quiet neighborhood is just 4 blocks from Dearborn Ave., with great entertainment, eclectic shopping and restaurants, live music, and more. 4 great beaches are a 5 minute drive from our front door-- and 15 minutes from Venice Island.

Top guest favourite
A light-filled living space features a gray sectional sofa adorned with striped cushions. A mid-century modern coffee table sits at the center, while natural light filters through the windows dressed in bamboo shades. A decorative rug adds warmth to the wooden flooring.
Cottage in Englewood
4.94 out of 5 average rating, 119 reviews

Bamboo Cottage, minutes to beach, no guest fee!

We pay Airbnb's Guest Fee. Save on Weekly and Monthly Stays! Discount automatically applies :). Welcome to The Bamboo Cottage! A peaceful and private 1940's Old Florida farmhouse tucked away in Englewood's Historical District. Centrally located within walking distance to Dearborn Street & Lemon Bay, and just miles to the beautiful beaches of Manasota Key!

Guest favourite
The exterior of a vibrant yellow bungalow is visible, surrounded by lush landscaping with palm trees and tropical plants. A screened-in porch extends from the front, and a white picket fence borders the property, providing an inviting entrance.
Flat in Englewood
4.83 out of 5 average rating, 130 reviews

BeachBay SeaHouse - 1521

Best location/value on Manasota Key in Englewood, FL... 300 yards to pristine gulf beaches, 300 yards to boat ramp and dock on Lemon Bay if you have a boat or want to see dolphin or fish off the dock. 4/10s of a mile to several great restaurants and 1 mile to Stump Pass State Park and a few more miles to walk via the park to Stump Pass.

Popular amenities for Englewood holiday rentals

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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 210 vacation rentals in Englewood Isles, and over 1,050 vacation rentals in Old Englewood Village.

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

    Yes! Work meets play with ease at over 460 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.

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

    Experience the best of Englewood with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Englewood house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 250 house rentals with pools in Englewood, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Englewood have a gym?

    Absolutely! We offer over 30 house rentals with a gym in Englewood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Englewood have a bbq area?

    Absolutely! We offer over 160 house rentals with a bbq area in Englewood. Enjoy a tailored experience with all the comforts you desire.

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

    Absolutely! We offer over 120 house rentals with self check-in in Englewood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Englewood have free parking?

    Absolutely! We offer over 500 house rentals with free parking in Englewood. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Englewood?

    Englewood has more than 490 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Englewood

  • Total holiday rentals

    Explore 1,090 holiday rentals in Englewood

  • Nightly prices starting at

    Englewood holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 25,350 verified reviews to help you choose

  • Family-friendly holiday rentals

    860 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 390 rentals that welcome pets

  • Holiday rentals with a pool

    580 properties feature pools

  • Rentals with dedicated workspaces

    500 properties have a dedicated workspace

  • Wifi availability

    1,080 of Englewood holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront and Free parking on premises across Englewood rentals

  • 4.9 Average rating

    Englewood stays are highly rated by guests – averaging 4.9 out of 5!

Destinations to explore

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