Luxury Vacation Rentals with a Private Pool in Englewood

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 17 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Englewood

Home in Venice

3 bedrooms•3 baths

New

Condo in Venice

2 bedrooms•2 baths

•

~$320 less than other sites

Condo in Venice

2 bedrooms•2 baths

•

New

~$255 less than other sites

Apartment in Venice

2 bedrooms•2 baths

•

New

~$270 less than other sites

Condo in Venice

3 bedrooms•2 baths

•

New

~$245 less than other sites

Home in Englewood

3 bedrooms•2 baths

•

New

~$105 less than other sites

Home in Englewood

3 bedrooms•2 baths

•

New

~$105 less than other sites

Home in Englewood

4 bedrooms•3 baths

•

New

~$220 less than other sites

Welcome to private poolside luxury in Englewood

Settle into luxury private-pool vacation rentals in Englewood where modern coastal design meets total privacy. Each Wander pairs a sparkling heated pool with sun shelf or spa, screened lanai living, and lush palms for a true at-home resort feel.

Inside, expect chef-worthy kitchens, premium linens, whole-home smart features, and ultra fast WiFi that keeps work humming without sacrificing downtime. Dedicated work nooks and blackout bedrooms make every schedule easy.

From waterfront sanctuaries with boat-friendly docks to quiet retreats near the key, every home is professionally maintained, immaculately cleaned, and supported by 24/7 concierge. Your pool is always the centerpiece, and your stay always looks exactly like the photos.

Available soon in Englewood

Home in Port Charlotte

3 bedrooms•2 baths

•

New

~$65 less than other sites

All homes in Englewood

Home in Venice

3 bedrooms•3 baths

New

Condo in Venice

2 bedrooms•2 baths

•

~$320 less than other sites

Condo in Venice

2 bedrooms•2 baths

•

New

~$255 less than other sites

Apartment in Venice

2 bedrooms•2 baths

•

New

~$270 less than other sites

Condo in Venice

3 bedrooms•2 baths

•

New

~$245 less than other sites

Home in Englewood

3 bedrooms•2 baths

•

New

~$105 less than other sites

Home in Englewood

3 bedrooms•2 baths

•

New

~$105 less than other sites

Home in Englewood

4 bedrooms•3 baths

•

New

~$220 less than other sites

View all homes

Highlights in Englewood

Discover Englewood's pristine Gulf beaches, rich coastal nature preserves, and charming historic downtown on Florida's scenic Lemon Bay.

Englewood Beach at Chadwick Park

Stump Pass Beach State Park

Historic Dearborn Street

Lemon Bay Aquatic Preserve

Blind Pass Beach

Myakka State Forest

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for private pool vacation rentals in Englewood

More popular private pool destinations near Englewood

Private pool vacation rentals in Siesta Key

Private pool vacation rentals in Captiva

Private pool vacation rentals in Cape Coral

Private pool vacation rentals in Bradenton

Private pool vacation rentals in South Bradenton

Private pool vacation rentals in Cortez

Private pool vacation rentals in Bradenton Beach

Private pool vacation rentals in Fort Myers

Other popular amenities & vacation types in Englewood

Family vacation rentals in Englewood

Pet-friendly vacation rentals in Englewood

Discover more beyond the pool in Englewood

Framed by Lemon Bay and the Gulf, Englewood blends uncrowded shoreline with a laid-back, upscale vibe. Spend slow mornings on Manasota Key, where Englewood Beach offers soft sand and Stump Pass State Park reveals unspoiled dunes, shelling, and seasonal turtle nests.

Beyond the beaches, glide a kayak through the Lemon Bay Aquatic Preserve to spot dolphins and manatees, or book a charter for tarpon runs near Boca Grande Pass. Cycle the Cape Haze Pioneer Trail, linger on Dearborn Street for gallery browsing and markets, then chase a glowing Gulf sunset.

With nature at your doorstep and everyday comforts close at hand, Wander’s luxury private-pool vacation rentals in Englewood are the perfect choice for work or leisure.

FAQs: Vacation Rentals in Englewood

Why should I book a Wander in Englewood over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.

Every home in Englewood delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular private pool vacation rentals in Englewood?

Some of our most popular private pool vacation rentals in Englewood include 25025 Spartina Dr, 17625 Opal Sand Dr #302, and 17595 Opal Sand 306. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different private pool vacation rentals does Wander have available in Englewood?

Wander offers 17 private pool vacation rentals in Englewood, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s private pool vacation rentals in Englewood?

You can check-in to Wander private pool vacation rentals in Englewood after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Englewood have WiFi access?

Yes. Every Wander home in Englewood has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.