Vacation rentals with a pool in Homestead

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Homestead

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite

Tiny homes in Cutler Bay

4.99 out of 5 average rating, 156 reviews

Quiet tropical Oasis setting with 1 bed and 1 bath

Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

Sep. 29 – Oct. 6

$229 CAD per night

Guest favourite

Guesthouse in Miami

4.96 out of 5 average rating, 167 reviews

Cozy private guest studio

Welcome! This is a private guesthouse located in a quiet neighborhood. Accommodations are with a private entrance and parking space to make you feel at home. We are located near a major expressway. We have a pool; The POOL is a SWIM AT YOUR OWN RISK. It is shared with Owner. Enjoy a smoke free cottage. Ashtrays are provided outside for those guest that do smoke. We provide a queen size bed and a couch/bed. This space is perfect and comfortable for two guest.Please NO children and NO animals.

Sep. 24 – Oct. 1

$165 CAD per night

Guest favourite

Home in Homestead

4.93 out of 5 average rating, 357 reviews

Private Paradise between Miami & the Keys

My 4/3 home is in the area known as the "Gateway to the Keys". Enjoy a comfortable stay for 10 people in 4 bed rooms. Great place for families & travelers. Very comfy home, & the back yard has the feel of a true tropical paradise. Good WIFI My cleaning crew & I work very hard to keep it clean and sterile due to COVID. NO ADDITIONAL GUESTS & NO DJs. NO PARTIES. I RESERVE THE RIGHT TO ENTER THE HOME IF I FEEL THERE IS AN UNAUTHORIZED PARTY/EVENT. FINES WILL BE APPLIED FOR NOISE VIOLATIONS.

Aug. 28 – Sep. 4

$546 CAD per night

Guest favourite

Apartment in Miami

4.87 out of 5 average rating, 336 reviews

South Beach King Suite

Situated in Miami Beach's premier neighborhood, this Art Deco hotel suite has been thoughtfully redesigned to provide everything you need for an unforgettable South Beach experience. From beach gear, to a convenient kitchenette for easy meal preparation.Indulge in a staycation with flair, complete with a rooftop deck and pool. Enjoy fast Wi-Fi, a smart TV equipped with Netflix, or venture out with the beach just steps from your door. The Miami Beach Convention Center is around the corner

Sep. 5 – 12

$212 CAD per night

Guest favourite

Guesthouse in Homestead

5.0 out of 5 average rating, 110 reviews

Guest house with pool and private hot tub

Beautiful modern new build, in a very tranquil setting and neighborhood. The guest house -bungalow has its own private parking and entrance as well as its own fenced in backyard. A large terrace for your outdoor enjoyment with gas BBQ. outdoor furniture HOT TUB and fire pit. The guest house has also access to a 40 ft. long pool. Fast WiFi also a PS4 game console. 2 blocks from a park where you can play basketball, soccer, skateboarding, kids water park, as well as gym equipment.

Oct. 18 – 25

$370 CAD per night

Guest favourite

Guest suite in Miami

4.9 out of 5 average rating, 355 reviews

Cozy Suite -Exterior Entrance, SelfCheckin

If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Room for you. We are conveniently located between Key Largo and Downtown Miami, in an upscale community. You’ll feel Safe and Welcome here! -GATEWAY to the Keys and Everglades -Private Entrance -Self Check-in -Free Parking -Fast WIFI -Bathroom with 2 sinks -SWIMMING POOL -Central A/C -HBO TV -Refrigerator -Ceiling Fan -Closet Space -Ceramic Tile Floors -Iron & Board -Towels & Bath essentials -Hair dryer

Sep. 7 – 14

$151 CAD per night

Superhost

Apartment in Miami

4.9 out of 5 average rating, 601 reviews

Tropical Suite in Miami Beach

A blend of elegance and tropical charm awaits you. Enjoy a renovated building with ultimate comfort. Dive into the 20m private pool where you can soak up the sun on the hotel's loungers while enjoying your time and relaxation , savor outdoor cooking shared with other guest, relax in the lush lobby, and rest in the refined bedroom with a King Bed Size, Netflix Tv, Central Ac and Mini Fridge . Craft extraordinary memories at our exceptional property.

Nov. 6 – 13

$219 CAD per night

Guest favourite

Guest suite in Miami

4.95 out of 5 average rating, 484 reviews

Refreshing Modern Retro Studio w/ pool &Jacuzzi

This Studio is located in the City of Miami. It has its own PRIVATE patio,pool,jacuzzi and parking with gate near to Coral Gables, little Havana, Brickell, Downtown Miami and only 20 minutes away from South beach. You won't only find a private and quiet place to stay but also a very detailed and sparkly clean place since we are the hosts and owner of the property too. And we follow a very strict cleaning protocol. Your Hosts Dunia and Arnel.

Jun. 10 – 17

$202 CAD per night

Guest favourite

Home in Miami

4.96 out of 5 average rating, 319 reviews

The Miracle Cottage & Pool on Acre Miami Florida

Beautiful, brand new PRIVATE cottage on an acre property situated in million dollar neighborhood. Perfect place to relax and enjoy the Miami sun. This is a little piece of heaven in the heart of a magical city. Come & enjoy your best vacation. Charming , peaceful & comfortable . Cottage is a completely separate building from the main house. It’s 900 sf of living area. Cleaning & Decontamination as per CDC guidelines before every check in.

Feb. 3 – 10

$289 CAD per night

Guest favourite

Farm stay in Homestead

4.92 out of 5 average rating, 155 reviews

Arritola B&B Ranch, is a unique farm experience!

Beautiful farm, with large heated pool and a lush tropical landscape. Your guest house is in the back of the property next to the chicken coop. The goats, pigs, bunnies and other small farm animals are friendly and will enjoy your company. This is the perfect spot for tourism as we’re within minutes of the Everglades National park, Florida Keys, Biscayne National Park, and much more. Owners live in the main house. You rent the guest house.

Jan. 3 – 10

$559 CAD per night

Guest favourite

Condo in Miami

4.96 out of 5 average rating, 270 reviews

Marriott Villas at Doral 2BD sleeps 8

Located in one of the most prestigious areas of Miami, Marriott's Villas at Doral are a tranquil hideaway; only 13 miles from the sizzling excitement of Miami Beach, yet a world away. Sharing the 650-acre lush landscape is the celebrated Trump National Doral Miami, a Trump-managed resort. There, you have access to four championship courses, a classic European spa, a water recreation playground and several restaurants.

Dec. 8 – 13

$224 CAD per night

Guest favourite

Guesthouse in Homestead

4.98 out of 5 average rating, 160 reviews

Charming Private Pool house for two.

Charming private back pool house on a fenced property in a quiet neighborhood close to US 1, the Turnpike, the Keys, Nascar and the Homestead Speedway, and the Everglades. You are 15-20 minutes from the Speedway, 20 minutes from the Everglades, and 30 minutes from Key Largo. For guests wishing to stay a month or more, I would require you to provide a copy of your photo ID.

Apr. 16 – 23

$138 CAD per night