Vacation rentals in Englewood

4.86 out of 5 average rating, 145 reviews

A bright loft bedroom features a spacious bed with a patterned duvet and colorful pillows. Large sliding doors provide access to a balcony with views of the Gulf. Two bedside lamps and decorative curtains complete the inviting space.

Townhouse in Siesta Key

"Relax Here" -Royal Palm Suite- Siesta Key Beach

The pampering begins HERE: 3 bed/ 2.5 baths townhouse, sqft 1,850, 2 kings & 1 queen bed, an enchanting loft bedroom with it's own balcony and incredible Gulf / Beach views All 3 balconies have Gulf views!! Imagine sitting on your patio and watching people at the beach. Gumbo Limbo Rentals is a mini resort, 60 steps to the beach with only 2 duplexes sharing a black bottom lagoon pool which is heated during the colder winter months. Free: Wifi, beach chairs & sun umbrellas, 2-3 parking spaces

Tiny home in Port Charlotte

5 out of 5 average rating, 6 reviews

Minutes to Sand, Dog Friendly, Hot Tub Luxury

Watch the stars from your hot tub! Not camping, not glamping... This is luxury living for less! Private dog friendly property. Hooked up to city water, cold air in all rooms, immediate demand hot water and septic. This slice of paradise is minutes from the sand and has an elegantly appointed private master, two private loft bedrooms, sleeper sofa & 9' vaulted ceilings. Your private retreat includes the use of two kayaks, gazebo, beach chairs, 5G Wi-fi & Netflix, Prime, Paramount. Paradise!

4.77 out of 5 average rating, 104 reviews

A bright studio apartment features a spacious bed dressed in light grey linens. Two bedside lamps provide soft illumination. A small kitchenette is visible, while a doorway leads to a bathroom with modern fixtures. Natural light enters through a door leading to the private patio.

Apartment in Siesta Key

Gertrude's Siesta | Patio & 1-min to Beach/Village

The Village Studio Top location on island! Apartment with full kitchen, private patio, gated courtyard, in world famous Siesta Village! Leave the car behind and walk to white-sand beaches, 20 bars and restaurants, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Experience a combination of fun ease and relaxation you can't get in other vacations! Book a special getaway now! - Tollbooth by AirbnbCorpMiddlemen, but this property is from GertrudeRentalsSiesta

4.88 out of 5 average rating, 153 reviews

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

A covered porch area features comfortable seating surrounding a low table, with a view of a heated pool. String lights create a soft illumination along the ceiling, while lush greenery surrounds the outdoor space, enhancing the tranquil atmosphere.

4.96 out of 5 average rating, 123 reviews

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

4.96 out of 5 average rating, 117 reviews

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

Summer 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.

4.92 out of 5 average rating, 119 reviews

An aerial view of a serene beach with soft white sand meeting clear turquoise waters. Beach loungers are positioned along the shore, and a few scattered beachgoers enjoy the sunny day. Lush greenery lines the edge of the beach, contributing to a calm coastal ambiance.

Condo in Siesta Key

Sea Shell Ocean view On Beach Walk everywhere Pool

Post Hurricane- Complex OPEN Enjoy ocean views in this 2 bed 2 bath spacious beach side 4th floor condo at Sea Shell Updated coastal decor across from Capt Curts, restaurants, grocery, coffee, ice cream Easy to WALK everywhere No car needed Perfect location Great for families Sleeps 6- 1 king & 2 queens & walk in closets Balcony with GULF views Private beach steps away from bldg. Free beach loungers. POOL Siesta Beach #1 in US Quick Wifi Superhost- 265+ reviews that ave FIVE STAR!

4.91 out of 5 average rating, 23 reviews

Home in North Fort Myers

Paradise Found

PARADISE FOUND, you can vacation right here at your own LAKE SIDE PARK! Stunning, peaceful & beautiful waterfront property with your own little island. Fish, bird watch or feed the turtles from your private dock or double arched bridge. Huge back yard for enjoyment & safety of children & pets. Your vacation home has a sunny disposition & soaring ceilings. First floor master suite with sliders to pool/lanai. Two story ceilings in livingroom & gorgeous staircase to guest suites.

A spacious outdoor deck is framed by wooden railings and surrounded by tropical foliage. The deck features seating arrangements under a shaded area, with large glass doors leading into the cottage. Sunlight filters through the trees, creating a serene environment.

4.91 out of 5 average rating, 11 reviews

Slowtide Cottage on Siesta Key

A high-end luxury cottage retreat on Siesta Key. No parties here -- the space was designed and outfitted for those who want a quiet place to relax. 2 bed 2 bath Cottage situated on the Intracoastal water of Siesta Key adjacent to the community pool, tiki bar, fishing dock, fishing pier and deeded private beach access. Meticulously remodeled former ww2 USAAF Barracks from the old SRQ Air Force Base. All new electrical, plumbing, lighting (Buster & Punch), Arhaus furniture.

4.87 out of 5 average rating, 126 reviews

A functional kitchen is equipped with stainless steel appliances, including a large refrigerator and a coffee maker. Light wood cabinetry offers ample storage. A decorative rug lies on the floor, and natural light filters through a window dressed with a light fabric curtain.

Home in Punta Gorda

Coastal cottage in Heart of Downtown

Quaint and airy historical cottage in the heart of downtown! THE BEST LOCATION...half a block to restaurants, just blocks from Harbor walk, less than a mile from Fisherman's Village. My home is tastefully decorated and gives you the feel of old Florida with all the conveniences. You can relax on the front porch swing or sip a cocktail and people watch! There is so much to do within walking distance of the house. And Punta Gorda always has something going on

4.92 out of 5 average rating, 204 reviews

A private outdoor patio is highlighted, featuring a round table surrounded by four chairs. A large blue umbrella provides shade, while tropical greenery adds a natural backdrop. Paved brick flooring completes the inviting outdoor space, ideal for relaxation.

Condo in Siesta Key

Steps to Beach & Siesta Key Village-Village condo

Steps from the sugary white sand of world famous Siesta Key Beach and the turquoise waters of the Gulf of Mexico. Our charming beach house is situated in a relaxing tropical setting with a private outdoor patio. It is ground level with a reserved parking space right in front of the unit. Newly renovated with tile floors, fully equipped kitchen with sleek granite counter-tops and pendant lighting, you will enjoy a warm and inviting atmosphere.

5 out of 5 average rating, 12 reviews

An outdoor dock area features several wooden Adirondack chairs in a warm orange hue, positioned by calm water. Sturdy posts with lantern tops line the dock, surrounded by lush greenery and palm trees. A clear sky and distant homes create a serene waterfront setting.

Home in Punta Gorda

Stunning! Luxury waterfront home

STUNNING!! LUXURY WATERFRONT HOME - HEATED POOL- Close to Harbor/Fish Village -PREMIER HOST reviews averaging 5.0 since 2018 on other site. -Modern, newly updated home with open layout allowing for enjoyment of the cool waterfront breezes. -Boat dock with very close Harbor access within 10 minutes. -Southern exposure, full sun, heated pool, and waterfront. Oversized pool extends along large portion of rear of home.

Vacation rentals for every style

Get the amount of space that is right for you

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A space thats all yours, with room for everyone

Popular amenities for Englewood vacation rentals

Self check-in

Pet friendly

Laptop-friendly workspace

Beachfront

Gym

Stay near Englewood's top sights

Chadwick Park at Englewood Beach181 locals recommend

Englewood Beach239 locals recommend

SandBar Tiki & Grille159 locals recommend

Stump Pass Beach State Park151 locals recommend

Farlows on the Water135 locals recommend

Lock 'N Key Restaurant113 locals recommend

Englewood beach vacation rentals

4.95 out of 5 average rating, 111 reviews

A spacious balcony offers a view of the Gulf, framed by lush greenery. Two wooden rocking chairs sit peacefully on the deck, accompanied by a small round table. The water shimmers in the distance, creating a serene coastal atmosphere.

Condo in Englewood

Sunset Beach

4.96 out of 5 average rating, 171 reviews

A comfortable living space features a blue sectional sofa and a patterned armchair, complemented by a wooden coffee table. Light streams in through a window with blinds, while a welcoming entry door adds to the serene ambiance.

Villa in Sarasota

Newly Renovated- 150 Yards to Beach & Restaurants!

A spacious bedroom features a elegant white bedframe with a black-and-white patterned comforter. A lamp sits on a nightstand beside the bed. A ceiling fan is visible above, and natural light enters through a window with multiple panes.

5 out of 5 average rating, 3 reviews

Walk to the beach.

4.96 out of 5 average rating, 101 reviews

An aerial view reveals a mid-century vacation villa surrounded by lush greenery and open spaces, with the coastline and sandy beach visible in the distance. The calm ocean water stretches towards the horizon beneath a partly cloudy sky.

Condo in Venice

Vintage Villa, Thirty-Five

4.93 out of 5 average rating, 226 reviews

An aerial view shows a wide sandy beach bordered by the calm turquoise water. The layout includes various buildings near the beach gate, with pathways leading to the beach area. Beachgoers can be seen enjoying the shore.

Condo in Siesta Key

Private Siesta Key Escape

4.91 out of 5 average rating, 139 reviews

An aerial view captures a serene beachside community, featuring palm trees and sandy areas leading to the beach. Nearby, tennis courts and landscaped spaces are visible, along with multiple buildings designed for guest accommodations, highlighting access to outdoor relaxation areas.

Condo in Sarasota

Cottage on Siesta Key Your own getaway!

4.85 out of 5 average rating, 101 reviews

A brightly colored three-story building stands under a starry night sky, surrounded by palm trees. Exterior lights illuminate the vibrant walls and large windows. A paved driveway leads up to the garage, flanked by landscaped greenery.

Condo in Sarasota

5209B Menorca Street - Siesta Key Village Condo

Apartment in Manasota Key

An outdoor deck features colorful seating arrangements with two turquoise chairs and a small table set against a backdrop of lush greenery. A patio umbrella provides shade, and a tropical-patterned rug adds a vibrant touch to the space.

4.92 out of 5 average rating, 12 reviews

DolphinCove 5035A Turtle Cove

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Pet-friendly vacation rentals in Englewood

4.98 out of 5 average rating, 47 reviews

A spacious master bedroom is depicted with a large bed and a sleek headboard. A modern office area is visible, featuring an ergonomic chair. Light enters through a window above the bed, while a mounted television adds to the contemporary design of the room.

Home in Osprey

Sarasota vacation Home!

5 out of 5 average rating, 8 reviews

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.

Home in Englewood

Pet Friendly Pool Home with Large Private Yard

4.92 out of 5 average rating, 100 reviews

The heated pool area is enclosed by a screened lanai, showcasing a turquoise pool surrounded by a sandy deck. Lush palm trees provide shade, while the orange wall adds a bright accent. Several seating options are available near the pool for relaxation.

Home in Port Charlotte

Heated Pool Paradise, Gulf Access, Pet Friendly

4.8 out of 5 average rating, 15 reviews

Venice, FL: Pet-Friendly Home Lido, Siesta Beach

4.83 out of 5 average rating, 12 reviews

A serene beach scene features a golden sunset reflecting off calm waters. Silhouettes of two individuals walk along the sandy shore, framed by palm trees in the foreground. Soft sands and a peaceful atmosphere invite relaxation and connection with nature.

Home in Port Charlotte

Florida Rental

4.9 out of 5 average rating, 102 reviews

A dining area features a wooden table surrounded by six chairs, complemented by a patterned tablecloth. A large TV mounted on the wall showcases a scene of The Beatles. A bench and a small outdoor-style table are positioned nearby on tile flooring.

Home in Englewood

Tranquil, pet-friendly-yard and 6 mins from beach

The open living area features a large television mounted on a red cabinet opposite a comfortable recliner. A separate dining space with wooden chairs is seen, while the kitchen showcases light-colored cabinetry and visible appliances. Natural light brightens the space through multiple windows.

5 out of 5 average rating, 6 reviews

2/2 Near Beaches. Smoke Free & Pet friendly!

A screened-in pool area is highlighted, featuring a sparkling swimming pool with a red float. Surrounding the pool are various seating options, including lounge chairs and a dining set, all set against a backdrop of lush greenery and a spacious fenced yard.

4.89 out of 5 average rating, 182 reviews

Venice Pool Villa with Bikes Kayaks & fun!

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House rentals in Englewood

4.93 out of 5 average rating, 72 reviews

A single-story cottage features a light blue exterior with a brown roof, framed by lush green grass and flowering plants. A small porch with railing provides entry, and a driveway leads to an attached garage on the left side.

Home in Punta Gorda

At Home in Seahorse Themed, Cozy Cottage

4.79 out of 5 average rating, 152 reviews

The entrance of the home is framed by lush greenery and vibrant flowering plants. The façade features large windows that provide ample natural light, while a covered porch welcomes guests. A clear blue sky complements the fresh and inviting exterior.

Home in North Port

3 bdrm Pool Home / Quiet Cul De Sac

4.96 out of 5 average rating, 113 reviews

A modern living area features a spacious gray sectional sofa paired with a wooden coffee table and a patterned rug. Bright light enters through large windows, highlighting a well-appointed kitchen with dark cabinetry and bar stools along the island.

Home in Cape Coral

Beautiful Waterfront House, Feels Like Home!

4.97 out of 5 average rating, 103 reviews

The modern kitchen features a central island with seating for four, surrounded by stainless steel appliances and light cabinetry. Natural light fills the space through a large window, highlighting the spacious layout that connects the dining and cooking areas.

Home in Arcadia

Hernando House 3/2 w private backyard and patio

4.9 out of 5 average rating, 42 reviews

A spacious bedroom is furnished with a plush bed dressed in soft neutral tones and decorative pillows. Two bedside tables flank the bed, each holding a lamp. Natural light fills the room, highlighting the warm color palette and elegant bedding.

Home in Port Charlotte

Charming home near the Beach and Punta Gorda.

A modern living room features a dark sectional sofa adorned with yellow cushions. Two patterned armchairs are positioned nearby. A coffee table sits in front, while a light area rug lies underfoot. Large glass doors open to a screened lanai, allowing natural light to fill the space.

4.92 out of 5 average rating, 52 reviews

Shell near the Sea, 2-Br Pet Friendly Home

4.95 out of 5 average rating, 39 reviews

A living area is showcased with a blend of comfort and style. A cozy sectional sofa is paired with a patterned armchair. A wall-mounted television is visible, and natural light filters through nearby windows. Decorative elements include a mirror and artwork, contributing to the welcoming atmosphere.

Home in North Port

Entire Home. 2/bd & 2/bath with Pool.