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Englewood vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Englewood

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

Guest favorite

Cottage in Englewood

4.89 out of 5 average rating, 103 reviews

Free bikes/kayaks/walk to beach/2bed/2bath #2

Unit # 2 Beautiful 2 bed 2 bath cottage, great space to relax with family and friends. With full kitchen/ garage/laundry/outdoor shower. WiFi/Free bikes, kayaks, beach toys. Great Lanai to spend wonderful afternoons. You will love to walk to the beach and enjoy the most breathtaking sunset pictures. This cottage is fully furnished beach style for a wonderful vacation feeling. You have not only the beach and the bay to explore, but great restaurants/bars and more just walking distance. Enjoy!

Jul 8 – 15

R2,712 ZAR per night
Superhost

Home in Englewood

4.93 out of 5 average rating, 120 reviews

Stunning Home, Saltwater Heated Pool By the Beach

Stunning home meticulously maintained both inside & out. Follow the sunshine & salty air & arrive at your home away from home. Whether cooking for one or ten, the chef in the group is certain to appreciate this fully upgraded, open concept kitchen. Start the day brewing coffee in the Keurig & end the day sharing a bottle of chilled Pinot from your wine fridge. Open the sliders & the party extends outdoors. Inflate the raft & spend your days daydreaming afloat in the heated, salt water pool.

Sep 30 – Oct 7

R3,224 ZAR per night
Guest favorite

Guesthouse in Englewood

4.97 out of 5 average rating, 198 reviews

Shabby chic cottage with pool one mile from beach

This adorable shabby chic decor style studio cottage for 2 is located on one acre of old Florida landscaping. Great area for walking, biking, for exercise. Included with this home is access to a pool and large, lovely lanai, just outside the door. Head south for 7 min to historic Dearborn St or north for 3 miles to Venice. This location offers peace and tranquility combined with accessibility to endless activities nearby. 2 twins OR one King, per your preference. The pool is unheated.

Jan 8 – 15

R2,392 ZAR per night

Popular amenities for Englewood vacation rentals

Stay near Englewood's top sights

Blind Pass Beach74 locals recommend
Ann & Chuck Dever Regional Park25 locals recommend
SandBar Tiki & Grille159 locals recommend
Farlows on the Water135 locals recommend
Walmart Supercenter71 locals recommend
Indian Mound Park23 locals recommend

Englewood beach vacation rentals

Guest favorite

Cottage in Nokomis

4.98 out of 5 average rating, 123 reviews

Staycation Sanctuary - 100% Smoke-Free Property

Jul 19 – 26

R2,264 ZAR per night
Guest favorite

Condo in Englewood

4.94 out of 5 average rating, 116 reviews

Gulf Side Condo Englewood Florida

Nov 18 – 25

R4,051 ZAR per night
Superhost

Guesthouse in Englewood

4.93 out of 5 average rating, 232 reviews

Gulf front romantic cottage in paradise

Dec 1 – 8

R6,288 ZAR per night
Guest favorite

Home in Englewood

4.98 out of 5 average rating, 106 reviews

PRIME Location! 60 Steps to PRIVATE BEACH Dogs OK!

Nov 12 – 19

R9,576 ZAR per night
Superhost

Guest suite in Venice

4.8 out of 5 average rating, 109 reviews

Venice large Studio Near Manasota Beach, King Bed

Jun 6 – 13

R2,306 ZAR per night
Guest favorite

Guesthouse in Osprey

4.99 out of 5 average rating, 281 reviews

Cozy Cottage by the Bay

Apr 7 – 14

R2,079 ZAR per night
Guest favorite

Home in Englewood

4.99 out of 5 average rating, 101 reviews

Paradise on the Bay

Nov 17 – 24

R7,976 ZAR per night
Guest favorite

Home in Port Charlotte

4.82 out of 5 average rating, 234 reviews

Bright and sunny Port Charlotte home

Jul 24 – 31

R2,372 ZAR per night
Guest favorite

Condo in Englewood

4.88 out of 5 average rating, 111 reviews

A Beautiful Sunset Awaits - Steps to Beach

Sep 25 – Oct 2

R3,402 ZAR per night
Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 298 reviews

*MAY SALE! Sarasota #1 Luxury Villa Pool/Beach!*

Jan 22 – 29

R11,147 ZAR per night
Guest favorite

Guest suite in Englewood

4.95 out of 5 average rating, 66 reviews

Cozy Studio with Balcony & View of Gulf!

Aug 26 – Sep 2

R2,310 ZAR per night
Guest favorite

Home in Venice

5.0 out of 5 average rating, 8 reviews

Oasis - The Agave

Apr 19 – 26

R1,996 ZAR per night

Englewood home rentals

Guest favorite

Home in Venice

4.92 out of 5 average rating, 103 reviews

A Dream Come True

Aug 7 – 14

R2,541 ZAR per night
Guest favorite

Home in Englewood

4.95 out of 5 average rating, 111 reviews

"Lighthouse" 7 mins from Beach, direct gulf access

Sep 1 – 8

R3,424 ZAR per night
Guest favorite

Home in Port Charlotte

4.98 out of 5 average rating, 137 reviews

Cute cheery peaceful canal home fishing fun 3B/2B

Nov 24 – Dec 1

R2,237 ZAR per night
Guest favorite

Home in Englewood

4.95 out of 5 average rating, 133 reviews

New Home w/ Pool, 10 mins to Manasota Key beaches

Sep 25 – Oct 2

R4,193 ZAR per night
Guest favorite

Home in Port Charlotte

4.84 out of 5 average rating, 210 reviews

Peaceful Port Charlotte 2Bd/2Ba on water

Aug 25 – Sep 1

R2,805 ZAR per night
Guest favorite

Home in Englewood

4.97 out of 5 average rating, 32 reviews

Unique-Cotton Cottage

Oct 29 – Nov 5

R2,258 ZAR per night
Guest favorite

Home in Englewood

4.91 out of 5 average rating, 35 reviews

Adorable Vacation Home,

Jul 6 – 13

R1,939 ZAR per night
Guest favorite

Home in Englewood

5.0 out of 5 average rating, 51 reviews

Our favorite quiet place

Jul 10 – 17

R2,434 ZAR per night
Guest favorite

Home in Englewood

4.89 out of 5 average rating, 66 reviews

Tranquil, pet-friendly-yard and close to the beach

Aug 22 – 29

R2,213 ZAR per night
Superhost

Home in Englewood

5.0 out of 5 average rating, 4 reviews

Pineapple Cottage

May 29 – Jun 5

R1,800 ZAR per night
Guest favorite

Home in Englewood

5.0 out of 5 average rating, 5 reviews

Newly renovated, cozy 2 bedroom

Aug 18 – 25

R1,970 ZAR per night
Guest favorite

Home in Englewood

5.0 out of 5 average rating, 25 reviews

"Lost Loon" Oceanfront Cottage by Roxy Rentals

Nov 11 – 18

R9,635 ZAR per night

Englewood villa rentals

Guest favorite

Villa in Siesta Key

4.9 out of 5 average rating, 133 reviews

Mermaid Villa Ocean Front!

Jul 3 – 10

R14,856 ZAR per night
Guest favorite

Villa in Englewood

4.92 out of 5 average rating, 85 reviews

Casa Blu: Serene Pool Villa, Close to Beach

Dec 2 – 9

R2,484 ZAR per night
Guest favorite

Villa in Rotonda West

5.0 out of 5 average rating, 15 reviews

Stunning Villa in Golfer's Paradise/Canal Views

May 7 – 14

R2,575 ZAR per night
Guest favorite

Villa in Englewood

5.0 out of 5 average rating, 27 reviews

Ocean View Two Bedroom Villa Manasota Key

Aug 9 – 16

R14,635 ZAR per night
Superhost

Villa in Englewood

4.71 out of 5 average rating, 7 reviews

Beach Amore

Aug 31 – Sep 7

R15,853 ZAR per night
Guest favorite

Villa in Englewood

4.97 out of 5 average rating, 86 reviews

STUNNING 3/2 beach+pool property! 2 kings/2 bunks!

Nov 7 – 14

R8,011 ZAR per night
Guest favorite

Villa in Rotonda West

5.0 out of 5 average rating, 46 reviews

Gulf Coast Floridian Villa with Pool

Sep 24 – Oct 1

R4,574 ZAR per night
Guest favorite

Villa in Rotonda West

5.0 out of 5 average rating, 14 reviews

Villa Riverside for 6 persons with private pool

Nov 3 – 10

R3,098 ZAR per night
Superhost

Villa in Englewood

5.0 out of 5 average rating, 4 reviews

Luxury 4 Bedroom Villa Englewood

Sep 3 – 10

R9,770 ZAR per night
Superhost

Villa in Englewood, Charlotte County

5.0 out of 5 average rating, 4 reviews

Englewood Beach Villa - Walk to the beach!

Dec 4 – 11

R4,442 ZAR per night
Guest favorite

Villa in Rotonda West

4.96 out of 5 average rating, 26 reviews

Dolphin Oasis - Villa Close to SW Florida Beaches

Aug 30 – Sep 6

R3,582 ZAR per night
Guest favorite

Villa in Rotonda West

5.0 out of 5 average rating, 37 reviews

Enjoy Sunny Waterfront Beaches, Golf/fishing Home

Apr 26 – May 3

R3,339 ZAR per night

Quick stats about vacation rentals in Englewood

Total rentals

690 properties

Rentals with dedicated workspaces

320 properties have a dedicated workspace

Rentals with a pool

310 properties have a pool

Pet-friendly rentals

240 properties allow pets

Family-friendly rentals

520 properties are a good fit for families

Total number of reviews

17K reviews

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

  • Are there vacation rentals near Englewood's top attractions?

    You're in luck! Stay at the heart of it all with our vacation rentals near Englewood's top attractions. We offer over 2,750 vacation rentals near Chadwick Park at Englewood Beach, over 2,750 vacation rentals near Lock ''N Key Restaurant, and over 2,750 vacation rentals near SandBar Tiki & Grille, and so much more! Experience the best of Englewood right on your doorstep.

  • What types of vacation rentals are available in Englewood?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Englewood. From over 340 house rentals, over 20 villa rentals to over 40 cottage rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Where should I stay in Englewood?

    Make yourself at home in Englewood by choosing from our most frequently booked neighborhoods. We have over 770 vacation rentals in Old Englewood Village, and over 130 vacation rentals in Englewood Isles.

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

    Yes! Work meets play with ease at over 320 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 240 vacation rentals for guests traveling with pets.

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

    Experience the best of Englewood with our villa rentals, starting at about $180 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Englewood vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 310 vacation homes with pools in Englewood, available on Airbnb. Make a splash and soak up the sun in style!

  • Do villa rentals in Englewood have a bbq area?

    Absolutely! We offer over 10 villa rentals with a bbq area in Englewood. Enjoy a tailored experience with all the comforts you desire.

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

    Absolutely! We offer over 10 villa rentals with self check-in in Englewood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Englewood have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Englewood. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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