Luxury Vacation Rentals with a Private Pool in Key Largo

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 165 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Key Largo

Marina Villa Mariner's Club 212

3 bedrooms•3 baths

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~$110 less than other sites

Marina Villa Mariner's Club 210

3 bedrooms•3 baths

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~$110 less than other sites

Key Largo Villa, Kawama J3, 3/3

3 bedrooms•3 baths

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~$70 less than other sites

Key Largo Ocean Shore Villa 2 with pool & boat slip

2 bedrooms•2 baths

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~$65 less than other sites

Key Largo Ocean Shore Villa 3 with pool & boat slip

2 bedrooms•2 baths

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~$65 less than other sites

Key Largo Ocean Shore Villa 1 with pool & boat slip

2 bedrooms•2 baths

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~$65 less than other sites

Luxury

Islamorada Island

6 bedrooms•6 baths

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~$2,355 less than other sites

The Coquina House at Coral Cove

3 bedrooms•3.5 baths

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New

~$705 less than other sites

Welcome to private poolside luxury in Key Largo

Escape to your own slice of the Keys. Wander delivers luxury private-pool vacation rentals in Key Largo that marry the polish of a five-star stay with the privacy of a beautifully run home.

Swim in a private pool just steps from airy living spaces, then transition to focus with ultrafast WiFi and work-friendly touches. Expect chef-grade kitchens, plush bedding, crisp design, and immaculate housekeeping. Every stay is supported by a 24/7 concierge and hotel-level standards.

Book with confidence, knowing every home looks like the photos and elevates downtime in the Florida sun.

Available soon in Key Largo

Casa Largo

2 bedrooms•2 baths

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~$80 less than other sites

Luxury

Front Beach, Paradise Villa, Islamorada FL Keys

7 bedrooms•8 baths

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New

~$2,030 less than other sites

Modern Mediterranean Villa w/ Pool & Games

5 bedrooms•3 baths

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~$265 less than other sites

Luxury

Brand new Villa with Pool/Jacuzzi/GameRoom

5 bedrooms•6 baths

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~$450 less than other sites

Villa / Pool, Jacuzzi, Pickleball

7 bedrooms•4 baths

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~$505 less than other sites

Gated Villa, Pool/Spa, Bball & Ping Pong

5 bedrooms•5 baths

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~$285 less than other sites

Brickell Towers

2 bedrooms•2 baths

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~$85 less than other sites

Condo in Miami

2 bedrooms•2 baths

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~$45 less than other sites

Featured private pool vacation rentals in Key Largo

Luxury

Modern Villa w Pool + Spacious Outdoor Living

5 bedrooms•5 baths

New

Luxury

New Modern Estate, Pool / Jacuzzi / GYM / Media Room

6 bedrooms•7 baths

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~$7,105 less than other sites

Luxury

Modern Lakefront Villa w/ Pool, Jacuzzi and Gym

5 bedrooms•5 baths

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~$360 less than other sites

Luxury

Luxury Villa w/ Rooftop Pool & Theater

3 bedrooms•4 baths

New

Luxury

E11 PH - 63 Combined 2

2 bedrooms•2.5 baths

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New

~$375 less than other sites

Luxury

E11 PH - 63 Combined 1

2 bedrooms•2.5 baths

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~$455 less than other sites

Luxury

Luxury Penthouse in Brickell

6 bedrooms•7 baths

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~$695 less than other sites

Lush Villa with heated Pool, Location

5 bedrooms•4 baths

Highlights in Key Largo

Dive into Key Largo's vibrant marine life, historic shipwrecks, and lush state parks in the diving capital of the world.

John Pennekamp Coral Reef State Park

Christ of the Abyss

Florida Keys Wild Bird Rehabilitation Center

Dagny Johnson Key Largo Hammock Botanical State Park

Spiegel Grove Wreck

African Queen Canal Cruise

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.

All homes in Key Largo

Marina Villa Mariner's Club 212

3 bedrooms•3 baths

•

~$110 less than other sites

Marina Villa Mariner's Club 210

3 bedrooms•3 baths

•

~$110 less than other sites

Key Largo Villa, Kawama J3, 3/3

3 bedrooms•3 baths

•

~$70 less than other sites

Key Largo Ocean Shore Villa 2 with pool & boat slip

2 bedrooms•2 baths

•

~$65 less than other sites

Key Largo Ocean Shore Villa 3 with pool & boat slip

2 bedrooms•2 baths

•

~$65 less than other sites

Key Largo Ocean Shore Villa 1 with pool & boat slip

2 bedrooms•2 baths

•

~$65 less than other sites

Luxury

Islamorada Island

6 bedrooms•6 baths

•

~$2,355 less than other sites

The Coquina House at Coral Cove

3 bedrooms•3.5 baths

•

New

~$705 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in Key Largo

Beach essentials (77)

Tennis court (10)

Ev charger (2)

Guest house (1)

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Discover more beyond the pool in Key Largo

Key Largo anchors the northern Florida Keys, where living coral reefs, clear shallows, and protected waters invite exploration. John Pennekamp Coral Reef State Park and the Florida Keys National Marine Sanctuary showcase technicolor reefs, wild dolphins, and sea turtles in a rare subtropical seascape.

Mornings can mean snorkeling over elkhorn coral, paddling quiet mangrove creeks, or chasing sailfish on bluewater charters. Afternoons drift into golden sunsets over Florida Bay and starry skies that feel close enough to touch. All of this ease and natural beauty is why Wander's luxury private-pool vacation rentals in Key Largo are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Key Largo

Why should I book a Wander in Key Largo 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 Key Largo 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 Key Largo?

Some of our most popular private pool vacation rentals in Key Largo include Marina Villa Mariner's Club 212, Marina Villa Mariner's Club 210, and Key Largo Villa, Kawama J3, 3/3. 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 Key Largo?

Wander offers 165 private pool vacation rentals in Key Largo, 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 Key Largo?

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

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

Yes. Every Wander home in Key Largo 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.