Pet-friendly holiday rentals in Englewood

Two dogs are seen standing near a large window, gazing outside towards a grassy area. Natural light enters the space, highlighting the cozy seating arrangement nearby. The setting features a calm and inviting atmosphere, framed by the greenery outside.

4.84 out of 5 average rating, 112 reviews

50 Shades of Fray !

Beachy Chic without going over board. Modern Stainless Steel Appliances with White Quartz Crystal counter tops with a pass through to Family Room. Perfect Cozy spot in Paradise for Vacations and a perfect Get away! Two bedrooms and a pull out couch. Newly Renovated home. Bright with natural light, A Happy and Healthy Place! Karaoke, Dancing, Food Drinks, Thrifty and Classy Shops. Yoga, Beach and Boating. Pet friendly. (hurricane Ian destroyed our fenced in backyard. will update when repaired.)

Guest suite in Port Charlotte

4.96 out of 5 average rating, 119 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.

4.9 out of 5 average rating, 156 reviews

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

Unit #1 Free kayak/bikes/walk to beach/fullcottage

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.

A vibrant blue exterior of the home is showcased, framed by tall palm trees under a partly cloudy sky. A spacious driveway is visible, providing ample parking space in front of the house, which features a welcoming façade with multiple windows.

4.98 out of 5 average rating, 131 reviews

PRIME Location! 60 Steps to PRIVATE BEACH Dogs OK!

Luxury Prime Island Location-Enjoy the best location on the island with our family & pet-friendly home (pets require approval & $200/pet fee). Just steps from our private beach & 1 mile from bars and restaurants, with a free shuttle service to beaches, dining, & nightlife. Relax in comfort w/ soft beds, a spacious couch, and flat-screen smart TVs in every room & fast WiFi. We offer bikes and beach equipment. 1 mile from Manasota Key public beach. Book now for the ultimate island retreat!

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.

4.99 out of 5 average rating, 109 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.

A circular gas fire pit is surrounded by four teal outdoor chairs on a gravel surface. Lush greenery and a privacy fence provide a serene backdrop, while a pool enclosure can be glimpsed in the distance under a clear blue sky.

5 out of 5 average rating, 116 reviews

*New Listing* ☀️TheAquaOasis🌴Pool-6 miles to beach

Welcome to the Aqua Oasis! This home was built in 2020 and located just 6 miles to multiple beaches in sunny Englewood, FL! The home consists of 3 bedrooms & 2 full baths, an option to heat the outdoor pool, relaxing outdoor chairs around a gas fire pit, fenced in back yard to let your pets roam, and a gas grill to whip up your favorite meals! If your family desires your own, private space and private pool, but you want close proximity to local beaches- THIS IS FOR YOU!

Four beach chairs with vibrant tropical patterns are positioned on sandy shore, facing the sparkling Gulf waters. The bright sunlight reflects off the water's surface, creating a serene coastal scene perfect for relaxation.

5 out of 5 average rating, 41 reviews

"Lost Loon" Oceanfront Cottage by Roxy Rentals

Welcome to Lost Loon Oceanfront Cottage, a beautifully renovated 2-bedroom, 2-bath retreat on the Gulf. Enjoy private beach access, outdoor dining, and the soothing sound of waves just steps away. Inside, find a fully equipped kitchen and beach essentials like chairs, boogie boards, and games. Perfect for families, friends, or solo travelers seeking coastal comfort and charm. One pet is welcome (other pets upon request). Please note: the property is not fenced.

A spacious outdoor lanai features comfortable seating arrangements with tropical-themed cushions, alongside a dining area. A saltwater pool is visible through the screened enclosure, surrounded by lush greenery. A grill is positioned nearby, offering a perfect space for al fresco dining.

4.91 out of 5 average rating, 172 reviews

Sleeps 10! Coastal Home, Heated Pool, Near Beach!

Follow the sunshine & salty air & arrive at your meticulously maintained 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.

4.96 out of 5 average rating, 201 reviews

A bright and airy kitchen area is visible, featuring white cabinetry and a refrigerator. A large island with bar seating is positioned in the foreground. Light-colored tile flooring complements the soft yellow walls, and natural light streams through a window, illuminating the space.

Bungalow in Englewood

TROPICAL OASIS, MINUTES FROM THE BEACH!!

This charming 2 bedroom/2 bathroom, dog friendly home in Englewood is located 2 miles away from our beautiful Manasota Beach. Call this your home away from home, as you will find a flat screen TV, free wireless internet and a gas grill, washer/dryer, and a fully equipped kitchen. Bring your boat (boat ramp is located in the neighborhood), bathing suits, beach towels and sunscreen. We have the rest ready for you.

4.97 out of 5 average rating, 119 reviews

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.

Guesthouse in Englewood

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.

4.83 out of 5 average rating, 129 reviews

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.

Apartment in Englewood

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.

4.95 out of 5 average rating, 434 reviews

A decorative table is displayed with a patterned tablecloth, featuring a stylish lamp and a small statue. An art piece hangs on the wall, depicting a simple bag. Various decorative items, including a book and a small decorative object, are arranged on the table.

Apartment in Englewood

Oz Cottage hot tub, Pool, 2.9 m beach

The Oz Cottage room apartment is funky with all kinds off nooks and crannies! Walking distance to Lemon bay for beautiful sunsets. Great restaurants with outdoor dining and music on Dearborn St. Tennis courts, wonderful Library and a nice park are all within walking distance. 2.9 miles to Englewood Beach

Popular amenities for Englewood pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A spacious screened-in pool area is showcased, featuring a large heated pool with clear blue water. Comfortable lounge chairs and an umbrella are positioned nearby, and a well-maintained outdoor area surrounded by greenery is visible beyond the pool.

4.98 out of 5 average rating, 100 reviews

Iguana Alley, Beach HEATed Saltwater Pool on Canal

5 out of 5 average rating, 7 reviews

The exterior of a single-story cottage is presented, featuring a light blue facade, large front windows, and a welcoming entrance. A palm tree and manicured lawn enhance the curb appeal, while a concrete pathway leads to the entrance, framed by soft landscaping.

Home in Port Charlotte

Sunny Florida Home | Private Yard + Patio

4.91 out of 5 average rating, 124 reviews

Home in Venice

Spacious 2 Bedroom Home | Near Beach | Heated Pool

5 out of 5 average rating, 9 reviews

Home in Rotonda West

Tropical Oasis, pool, pelaton, golf, dog friendly

A white wooden gate marked with a sign reading 'Waterfront Getaway Vacation Rental' provides access to the property. The gate opens to a gravel pathway leading to the house, surrounded by clear blue skies and a well-maintained outdoor area.

4.93 out of 5 average rating, 71 reviews

Waterfront Getaway, a Boating Paradise

A private, screened patio houses a heated saltwater pool with clear, inviting water. Surrounding greenery includes lush palms and a spacious lawn. A lounge chair and a blue pool float are visible, creating a relaxing environment for outdoor enjoyment.

5 out of 5 average rating, 17 reviews

Coral Cottage

A inviting backyard space features a heated swimming pool surrounded by tropical plants and comfortable lounge seating. A hot tub is positioned nearby, with decorative accents including painted tiles and charming garden sculptures. A clear blue sky and fluffy clouds provide a serene backdrop.

4.9 out of 5 average rating, 90 reviews

Englewood Cottage with Pool, Hot Tub, and Fire Pit

A spacious living area features a large, light green sectional sofa surrounded by accent chairs. A floor lamp provides soft illumination, while decorative plants add a touch of nature. Soft, colorful rugs enhance the inviting ambience, complemented by natural light filtering through a partially covered window.

5 out of 5 average rating, 11 reviews

Newly Renovated, 2/2, Large Patio, Dock, Boat Lift

Pet-friendly home rentals with a pool

4.98 out of 5 average rating, 47 reviews

Home in Venice

Venice Retreat-Saltwater Pool+Hot Tub+Near Beach

The private solar-heated pool features a clear blue surface and is surrounded by a secure fence. Two lounge chairs are positioned along the edge, offering a relaxing spot to enjoy the outdoors. A beach ball floats gently on the water's surface.

5 out of 5 average rating, 14 reviews

Pet Friendly Pool Home with Large Private Yard

The entryway features a welcoming message on the wall, accompanied by a decorative wreath and a small side table in a vibrant red hue. A patterned area rug lies beneath, adding a touch of comfort to the space, which is illuminated by natural light from the nearby door.

4.85 out of 5 average rating, 150 reviews

Gulfstream Haven

5 out of 5 average rating, 3 reviews

A modern single-story home is surrounded by well-maintained landscaping, featuring lush greenery and palm trees. The entrance is marked by double doors, with large windows providing ample natural light. Blue window awnings complement the exterior, creating a comfortable and inviting appearance.

Home in Port Charlotte

Luxury NW Port Charlotte Retreat, pool/spa, canal

5 out of 5 average rating, 16 reviews

A private heated pool and spa are set within a screened enclosure. Four lounge chairs are positioned along the poolside, with colorful inflatable floats resting on the water's surface. Lush greenery can be seen through the enclosure, enhancing the serene atmosphere.

Home in Rotonda West

Luxury Golf Villa w/ Heated Pool & Spa

The exterior of a mid-century modern home is showcased, featuring a clean white facade and a welcoming porch. A manicured lawn with shrubs and palm trees surrounds the property. An American flag is displayed, adding a touch of character to the serene landscape.

5 out of 5 average rating, 22 reviews

The Mangrove House

5 out of 5 average rating, 15 reviews

A serene pool area is surrounded by lush greenery and palm trees. A vibrant inflatable in the shape of a dog floats in the clear water. Comfortable lounge chairs are positioned nearby, inviting relaxation under the sunny sky.

Home in Venice

Tropical Bliss | Lush Garden Poolside Retreat

5 out of 5 average rating, 23 reviews

A swimming pool is surrounded by a screened enclosure, featuring a shaded seating area with a thatched umbrella. The clear water reflects the sunlight, and a built-in ledge invites relaxation. Lush greenery is visible beyond the pool area, creating a serene outdoor environment.

Home in Long Meadow

Golden Pond Villa! Minutes from Boca Grande!

Private, pet-friendly home rentals

4.95 out of 5 average rating, 22 reviews

An aerial view of a spacious villa surrounded by lush greenery and a serene canal. The well-maintained lawn is accentuated by landscaped gardens with colorful flowers, while nearby homes are visible in the peaceful neighborhood.

Villa in Long Meadow

Stunning Villa in Golfer's Paradise/Canal Views

5 out of 5 average rating, 3 reviews

A scenic view features a vibrant sunset over Lemon Bay, with hues of orange, pink, and purple filling the sky. A silhouette of a palm tree stands in the foreground, alongside a private dock extending into the water, enhancing the tranquil setting.

Villa in Englewood

The Yellowtail

Campervan/RV in Englewood

A spacious kitchen area features modern cabinetry and a wooden countertop, accommodating a sink and a coffee maker. Natural light streams through the window adorned with a simple curtain. An entrance to the bathroom and a view of the bedroom are visible in the background.

4.88 out of 5 average rating, 16 reviews

Classic Airstream in a private oasis

Holiday home in Englewood

A tranquil shoreline is observed, with gentle waves lapping at the sandy beach. The sky displays soft hues of pink and blue as the sun sets over the Gulf of Mexico, creating a serene coastal scene.

4.95 out of 5 average rating, 58 reviews

Ocean view, Totally remodeled, Beach Home!

A vibrant sunset is captured beyond the horizon, casting a warm glow over the beach. A silhouette of a palm tree stands in the foreground, while people are seen walking along the sand. The scene is framed by a wooden walkway leading to the shore.

4.92 out of 5 average rating, 24 reviews

Lil Nauti South is a perfect place to unwind.

A sandy area is seen leading to calm turquoise waters, with a few palm trees standing nearby. The sky is clear and blue, complementing the tranquil beach setting. Steps can be seen leading down towards the water's edge.

5 out of 5 average rating, 20 reviews

Luxury Beach Front 1 BR, private hot tub & deck

An open living space is shown with a ceiling fan and recessed lighting. A comfortable armchair is positioned beside a stylish entertainment unit with a flat-screen TV mounted above. Decorative plants add a touch of greenery, while light-colored walls contribute to the bright atmosphere.

4.96 out of 5 average rating, 26 reviews

Stylish and Peaceful Home