
Holiday rentals with a pool in Englewood
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Englewood

Total holiday rentals
Explore 560 holiday rentals in Englewood

Nightly prices starting at
Englewood holiday rentals start at $52 SGD per night before taxes and fees

Verified guest reviews
Over 11,860 verified reviews to help you choose

Family-friendly holiday rentals
470 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 130 rentals that welcome pets

Rentals with dedicated workspaces
280 properties have a dedicated workspace

Wifi availability
560 of Englewood holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Englewood rentals

4.9 Average rating
Englewood stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated rentals with a pool in Englewood
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Escape to Casa Blu- private pool, minutes to beach
Your next retreat to Florida paradise should be Casa Blu with it's private pool and serene backyard. It's just minutes to area beaches, restaurants and parks. Let the stresses of daily life melt away as you float in the salt water pool, sipping margaritas, listening to Jimmy Buffett singing "It's Five O' Clock Somewhere" The single-floor layout, comfy bedrooms with private baths await. Fast WiFi, Smart TVs, and fully equipped kitchen. Everything's covered, from beach gear to a pack 'n play.

Gulf Front Escape + Beach Access
🦩 Exclusive Amenities Include: • Walk Out to the Beach – Steps from Your Door • Coastal & Surf Decks - Outdoor Seating • Historic Old Florida Charm • Beach Towels, Chairs & Umbrellas Provided • Community Pool with Picnic Tables & Chaise Lounges • Community Grills & Post-Beach Outdoor Showers • Free WiFi & TV • Coffee Maker & Kitchenette Smallwares Provided • Starter Packs of Essentials for Kitchen & Bath • Enhanced Cleaning Protocols • Combo Tub/Shower Bathroom • Desk/Chair in Unit

1mi to Beach. 1+ acre of jungle Pool & Pickleball
Over 1.2 acres of scenic Florida landscape to explore. Home to 50+ different plants, birds, animals and walking trails you are sure to feel like you are in a jungle. Just 1 mile to Manasota Beach the shark tooth capital! Explore all the beach has to offer with a 3-4min car/bike ride. huge lanai with pool, tv and seating areas. Just ten 5 min away 20+ restaurants/stores. We have a guest house in the back my wife & I live in depending on the year. We help local kids at the court with basketball

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.

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN
Luxury beach house with pool in a charming old-FL beach town, one of FL’s best kept secrets! New kitchen, 2 covered balconies & a walled backyard oasis. Spend sunny days by turquoise waters of the Gulf & host a cookout on the covered patio & pool. Enjoy the sea breeze while sipping your favorite beverage on the covered balcony off the living area. Lounge in style in the patio or go for a swim in the 6’ deep heated pool. You're walking distance to restaurants/bars and 57 seconds to the beach!

Waterfront| Pool & Spa | Near Beach| No Extra Fees
Welcome to Casa-A-Mar, your private slice of coastal paradise at our newly updated waterfront retreat. Step outside and launch straight into the water with direct Gulf access or into Lemon Bay—perfect for exploring the canals on one of our kayaks. Prefer to stay in? Spend your time in the heated pool, then ease into the hot tub as the sun sets. As evening falls, transform the backyard into your own open-air theater with our outdoor projector, perfect for movie nights under the stars 🌟

*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!

Lux Home on Gulf w/Private POOL & 50ft Dock
Rest your feet & your soul as you getaway from it all! This luxurious little piece of paradise is tucked away on a quiet Gulf Coast waterway. 10min from Englewood Beach and 5 min from stores. Tie your boat up in the back yard to the private 50 ft dock. Spend your days fishing, catching sunsets or in the pool every evening! Easy access to Don Pedro Island, local sandbars, inlet and several restaurants, all at your fingertips! Pack your bags, kick back- paradise is waiting!

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!

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.

Luxury Beach Retreat w/ Heated Pool
Welcome to our luxurious home, just 5 minutes from Manasota Key! Enjoy two master suites, a bunk room, and a gourmet kitchen with granite countertops. Relax in the screened lanai with a heated pool, outdoor dining, and lounge chairs. Additional features include high-speed internet, smart TVs, and an attached garage with entertainment options. Perfect for families or groups, this home is your ideal coastal retreat for relaxation and fun!

Canal-Front 3BR – Pool, Hot Tub & Boat Access
Experience Old Florida charm reimagined for modern coastal living at this fully renovated 1960 canal-front retreat in Englewood. With direct boating access to Lemon Bay and Stump Pass, private dock for up to a 30ft boat, heated pool, hot tub, outdoor bar lounge, and premium indoor-outdoor sound system, this 3BR waterfront escape blends heritage, luxury, and laid-back Gulf Coast living just minutes from beaches and waterfront dining.
Popular amenities for Englewood rentals with a pool
House rentals with a pool

Pool Haven by The Private Beach, Dog Friendly

Coastal Sanctuary - Pool & Privacy

Your Coastal Getaway!

Edison's Pool House

6min to Beach. Saltwater Pool, Jacuzzi. Fits 8ppl.

Paradise Palms | Private Pool | 10 min to Beach

Heated Spa Waterfront Home | Port Charlotte, FL

Pebble House w/ Screened Pool, Horseshoes, & more
Apartment rentals with a pool

Sunset Beach

Bay Breeze @ManasotaKeyCondos

Entire Beachside Condo! Don’t worry Beach Happy!

Vintage Villa 35 | Steps to Beach | Pool

Studio, pool, private beach, boat dock shark teeth

Spacious Beachfront 3br Manasota Key Condo

A little slice of paradise

Boardwalk Beachfront Getaway
Other holiday rentals with a pool

Luxury House Florida, Golf View, Privacy Pool.

3 Bedroom Home | Heated Pool | Close to Beaches

10 mins to Beach, Heated Pool, Beach Gear & Games

Englewood Beach Villa - 3 min Walk to the Beach!

Pool Home Walkable to Shops and Dining

Water view Villa private Heated Pool golf beach

The Mangrove House

Stunning Lemon Bay Water & Sunset Facing Home!
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $258 SGD | $314 SGD | $313 SGD | $257 SGD | $225 SGD | $221 SGD | $226 SGD | $208 SGD | $200 SGD | $200 SGD | $217 SGD | $235 SGD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Destinations to explore
- Miami Holiday rentals
- Four Corners Holiday rentals
- Miami Beach Holiday rentals
- Orlando Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Hollywood Holiday rentals
- Jacksonville Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- St. Augustine Holiday rentals
- Cape Coral Holiday rentals
- Rentals with a washing machine and dryer Englewood
- Fitness-friendly rentals Englewood
- Waterfront rentals Englewood
- Rentals with beach access Englewood
- Rentals with outdoor seating Englewood
- Pet-friendly rentals Englewood
- Beach house rentals Englewood
- Rentals with a patio Englewood
- Family-friendly rentals Englewood
- Rentals with a kayak Englewood
- Rentals with a firepit Englewood
- Beachfront rentals Englewood
- Rentals with lake access Englewood
- Beach apartment rentals Englewood
- Flat rentals Englewood
- House rentals Englewood
- Rentals with a hot tub Englewood
- Apartment rentals Englewood
- Rentals with a fireplace Englewood
- Villa rentals Englewood
- Rentals with pools Sarasota County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Siesta Beach
- Captiva Island
- Anna Maria Island Beach
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Turtle Beach
- Caspersen Beach
- Manasota Key Beach
- Crescent Beach
- Englewood Beach
- Anna Maria Public Beach
- River Strand Golf and Country Club
- Lovers Key Beach
- Cortez Beach
- Img Academy
- Myakka River State Park
- Florida Gulf Coast University
- Stump Pass Beach State Park
- Blind Pass Beach
- Lido Beach
- North Jetty Beach
- Bowman's Beach





