Vacation rentals with a pool in Cutler Bay

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cutler Bay

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

0 of 0 items showing

1 of 3 pages

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

Treehouse in Cutler Bay

4.93 out of 5 average rating, 123 reviews

Cozy Treehouse in Private Garden, Pool & Hot Tub

Read entire listing for FAQ Contact AIRBNB for changes to your reservation We welcome all! Come reconnect with yourself and nature in this Zen garden. Surrounded by love, peace, nature in peaceful surroundings Located between Miami Beach & The Keys Beautiful & Quiet Residential Area South of Miami Close to all major roads. *this is a treehouse, so it is a small space, FULL SIZE bed (54 x 75 inches). Private bathroom adjacent to treehouse. Look at our other listings in main house.

Jun. 19 – 26

$202 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

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

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

Superhost

Home in Cutler Bay

4.99 out of 5 average rating, 149 reviews

Luxe 5BR Pool Jacuzzi Basketball

Heated pool/Jacuzzi/Basketball court/5BR Luxurious for a relaxing vacation, enjoying the warm weather of Miami. In this space you can enjoy a large heated pool and Jacuzzi with umbrellas, loungers and tables to enjoy a snack. All decorated with great taste and care in each of the rooms. In addition, for sports lovers, we have a basketball court. The perfect space for your family and friends. We are available 24 hours a day for any questions.

Mar. 3 – 10

$1,245 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

Superhost

Farm stay in Homestead

4.82 out of 5 average rating, 177 reviews

Cedar Room on Farm near Everglades & Florida Keys

We are located 8 miles from the Everglades National Park and 3 miles from Schnebly Winery. We are a small farm in the process of planting a tree grove. The room we offer is our Cedar Repurpose and Reuse room. All the wood on the walls and ceilings are from a Mansion in Miami that was being tore down.

Mar. 29 – Apr. 5

$145 CAD per night

Guest favourite

Guest suite in Miami

4.94 out of 5 average rating, 154 reviews

Sparkling Clean🌟Brand New Luxury Studio with Pool🏊🏼‍♂️

Beautiful New Designer Studio with pool access. Located in Southwest Miami, 8 minutes to shopping at The Falls and 10 minutes to Dadeland Mall, many delicious restaurants to choose from nearby, Miami Zoo just 5 miles away and 20 minutes to Matheson Hammock Park and Beach. Come stay like the locals.

Jun. 12 – 19

$139 CAD per night

Guest favourite

Villa in Cutler Bay

4.93 out of 5 average rating, 142 reviews

Luxurious house with pool and recreational areas.

Incredible house with 5 bedrooms, 3 bathrooms, large spaces, basketball court, billiards, ping pong, mini golf, heated pool, children's games, barbecue, in one of the best areas of Miami, close to the zoo, beaches, restaurants and recreational and commercial centers.

Dec. 13 – 20

$1,384 CAD per night