
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 £30 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.

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. Two bedrooms and 1 bathroom with a tub. Just ten 5 min away 20+ restaurants and grocery stores. We have a guest house in the back my wife & I live in depending on the year

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

Englewood Private Paradise near beach
This wonderful estate is ready to be your temporary home. With 2600 ft of luxury and exterior cameras for your peace of mind, you are more than inclined to relax at this gorgeous location. Close to restaurants and parks such as Manasota Beach, Stump Pass Beach Park and others, this is an ideal location. This custom-built home features 3 bedrooms, 2.5 baths, saltwater, heated pool with a waterfall, outdoor shower and an oversized 2.5 car garage. Perfect vacation home. Beach just 5 minutes away.

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 🌟

Heated Pool—Manasota Key—Dog Friendly
“Leisurely breakfasts out on the lanai while our dogs basked in the sunshine.” That's what guests keep saying about our Englewood home, 10 minutes from Manasota Key. Mornings start with breakfast on the lanai while your dogs claim the fenced yard. Afternoons are for the pool - kids on floats, the grill going for dinner. Sleeps nine, queen master with pool sliders, second queen, full-over-full bunk with trundle. Bikes and beach chairs in the garage, Publix 7 minutes away.

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!

Manasota Tree House • Private Beach & Bay Access
Welcome to Manasota Tree House, our piece of paradise on Manasota Key. The location is the best on the island & we are family friendly. Just steps to the bay & a short walk to private beach access, 1 mile to bars & restaurants w/ free shuttle! Amazing beds, comfy couches, flat screen smart TV's & free fast Wifi. Private over sized lot, outdoor quiet oasis under the beautiful trees w/ chairs & gas grill, 2 SUP's, beach chairs, & towels. 1 mile to public Englewood Beach.

Stunning Bay Waterfront! Jaw dropping Views!
Spectacular Lemon Bay views! Upstairs at Blue Island Inn, waterfront “Bella Vista” with Bay & Pool views! 2 bedrooms; kitchen & family room. Enjoy “Lemon Bay-front beach” in backyard. Low-key quiet vacationers. 1 car parking spot. No visitor parking. Free 2 kayaks. Login to your favorite streaming services with Smart TVs. Beautiful Blind Pass Beach, Englewood Beach, 5 restaurants & Tiki Bars are just 1.5 mile away or hop on Stumpy's Free Shuttle (tip based)

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!

Luxury House Florida, Golf View, Privacy Pool.
Enjoy a Stylish Experience at this Centrally-Located Place. Rotonda West A Deed Restricted Community. Located on the SouthWest Coast of Florida. Gulf of America Best Beach 12 min. Boating is popular in Lemon Bay and around Boca Grande. Around the Rotonda a Lot of Gulf Places, Water Canal, Lakes. GOLFING, BOATING, FISHING, TENNIS,HIKING, CLUBS & GROUPS. Is a lovely, established community in the picturesque area known as Cape Haze.
Popular amenities for Englewood rentals with a pool
House rentals with a pool

Englewood, Fl 2 bedroom home with heated pool.

Island Home & Casita, Pool, Golf Cart, Beach

Mango Beach Cottage with a swim spa

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

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

Edison's Pool House

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

BayFront 2.5 ac Private Gem 2 King bds + Game room
Apartment rentals with a pool

Sunset Beach

Bay Breeze @ManasotaKeyCondos

Entire Beachside Condo! Don’t worry Beach Happy!

Ocean Oasis on Manasota Key - Ocean View

Vintage Villa 35 | Steps to Beach | Pool

Studio, pool, private beach, boat dock shark teeth

A little slice of paradise

Boardwalk Beachfront Getaway
Other holiday rentals with a pool

Modern 3BR Retreat | Near Beach, Fishing & Golf

Coastal Sanctuary - Pool & Privacy

Your Coastal Getaway!

Trails End Two

Saltwater Villa/Pool/Jacuzzi/MovieTheater/FishDock

Water view Villa private Heated Pool golf beach

Paradise Palms | Private Pool | 10 min to Beach

3 Bed/2bath beautiful New Home with Pool
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £152 | £184 | £183 | £151 | £132 | £130 | £133 | £122 | £117 | £117 | £127 | £138 |
| 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 |
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- Anna Maria Island
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