
Holiday rentals with a pool in Englewood
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Englewood
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Waterfront, 3 Bed, 3 Bath, Pool/Hot Tub, Kayak
Relax with the whole family at this peaceful place to stay right on the intercoastal. Enjoy the newly renovated amenities this home has to offer. Enjoy a meal in the brand new kitchen, relax in the pool/hot tub, grill poolside, take kayak's out or paddle board to float with the dolphins and soak in the beautiful sunsets. Your stay will reinvent what true relaxation feels like! Enjoy our neighborhood restaurant just walking distance from the front door. This home has the "Coastal Charm" you need!

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.

Private 1mi to Beach. 1+ acre 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 oasis. Just 1 mile to Manasota Beach the shark tooth capital of the world! Explore all the beach has to offer with a 3-4min car/bike ride. The house has a 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. Escape the noise and enjoy nature.

Turtle Bay - minutes to Boca Grande!
Welcome to Turtle Bay Haven – Your Dream Escape on the Gulf Coast! Stay in your own private natural oasis, surrounded by lush greenery and the vibrant tropics of Florida wildlife. - Grocery Stores: just 5-10 min away - Dining Options: A variety of local restaurants are just min away. - Boca Grande: 11 mi (20 min) away, known for stunning beaches. - Manasota Key Beaches : 10 mi (20 min) - Activities: Kayaking, paddleboarding, fishing, hiking, biking, and over 20 golf courses await!

Free Heated Pool! Mins from Beach! Private Oasis!
Discover your dream getaway at this stunning 3BR tropical oasis just 5 miles from Englewood Beach! Start your mornings on the screened lanai with coffee, then dive into the heated pool featuring a swim-up bar. Surrounded by lush landscaping, this private escape offers comfort, style, and relaxation. Perfect for families, couples, or friends—close to beaches, golf, dining, and more. Book now and enjoy the ultimate Florida retreat filled with sun, fun, and unforgettable memories!

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.

Lux Home on Gulf w/Private POOL & 100ft 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 100 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!

Tropical Oasis, pool, golf, dog friendly
🌴 Tropical Oasis w/ Heated Saltwater Pool – Perfect for Families! 🏡 Small dog friendly 🐕 (pet fee: $150 for the first week, then $50 per additional week). This spacious 4BR, 3BA home sleeps 12 guests! Features include a king master suite, 2 queen guest rooms, & a bunk room (sleeps 6). Enjoy a heated saltwater pool, outdoor dining, & BBQ area. Inside, relax with a large TV, games. Close to beaches, shopping, & attractions! Book now for the ultimate getaway! ☀️🏖

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!

Studio, pool, private beach, boat dock shark teeth
Enjoy it all -Pool, private dock & private beach access-located near restaurants. Covered parking or hop on a shuttle to explore Manasota Key! Light, bright condo is complete with everything you will need to relax. Kitchenette has all the must haves-air fryer, portable stove, coffee maker, kettle & community grill. Enjoy a queen bed, shower and community washer/dryer. Fish off the pier, reserve a dock or check out the private beach.
Popular amenities for Englewood rentals with a pool
House rentals with a pool

Manasota Tree House: Private Beach & Bay Access

Luxury Casa in Venice

Specious Golf Getaway: Heated Pool/Sunset n.Beach

❤ROTONDA RETREAT❤*Spacious*Fully Furnished*Pool*

The perfect retreat with canal view

Your Coastal Getaway!

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

Golden Pond Villa! Minutes from Boca Grande!
Apartment rentals with a pool

On Manasota Key w direct access to our Beach! (A)

Bayside Escape-Condo w/ Dock, Pool, and Near Beach

Waterfront w/ Pool, mins to SK Beaches, bikes/sups

Location! Gulf Condo @ S. Jetty 30 day minimum

Gulf View! 2/1 with Heated Pool, Kayaks and SUP

Vintage Villa, Thirty-Five

Private Beach, Fishing Dock & Heated Pool Paradise

Beach Bliss Retreat on Manasota Key - Ocean View
Other holiday rentals with a pool

Pool Home Minutes From The Beach

Boaters Dream, full refund*, heated pool, sleeps 6

CLEAN*Great Location*Dockage Available*HEATED Pool

Luxury Retreat: Oasis with Pool & Putting Green.

Beautiful Floridian Oasis

☀Tropical Oasis☀Heated pool & amazing location!☀

Lake, Trees, Near Beach, with Private Heated Pool!

Steps to the beach on Manasota Key with POOL
When is the best time to visit Englewood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $257 SGD | $302 SGD | $315 SGD | $256 SGD | $224 SGD | $220 SGD | $225 SGD | $207 SGD | $199 SGD | $211 SGD | $212 SGD | $221 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 |
Quick stats about holiday rentals with a pool in Englewood

Total holiday rentals
Explore 520 holiday rentals in Englewood

Nightly prices starting at
Englewood holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 11,700 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 130 rentals that welcome pets

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wifi availability
510 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!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Fitness-friendly rentals Englewood
- Rentals with a patio Englewood
- Waterfront rentals Englewood
- Rentals with a washing machine and dryer Englewood
- Family-friendly rentals Englewood
- Rentals with a firepit Englewood
- Rentals with lake access Englewood
- Flat rentals Englewood
- House rentals Englewood
- Villa rentals Englewood
- Rentals with outdoor seating Englewood
- Rentals with beach access Englewood
- Beach apartment rentals Englewood
- Beach house rentals Englewood
- Rentals with a fireplace Englewood
- Apartment rentals Englewood
- Beachfront rentals Englewood
- Rentals with a kayak Englewood
- Pet-friendly rentals Englewood
- Rentals with a hot tub Englewood
- Rentals with pools Sarasota County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Captiva Island
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Cortez Beach
- Lido Key Beach
- Anna Maria Public Beach
- Bean Point Beach
- Manasota Key Beach
- Lovers Key Beach
- River Strand Golf and Country Club
- Englewood Beach
- Myakka River State Park
- Point Of Rocks
- Lakewood National Golf Club
- Marie Selby Botanical Gardens
- Stump Pass Beach State Park
- Blind Pass Beach
- South Jetty Beach
- Tara Golf & Country Club
- Boca Grande Pass




