Holiday 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.

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Guest favourite

Tiny home in Cutler Bay

4.99 out of 5 average rating, 159 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.

5–12 Sep

$196 SGD 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.

5–12 Jul

$156 SGD per night

Guest favourite

Guest house in Miami

4.96 out of 5 average rating, 168 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.

10–17 Sep

$137 SGD per night

Guest favourite

Home in Cutler Bay

5.0 out of 5 average rating, 124 reviews

Private Villa Pool Spa Games-Beach

Located within a private cul-de-sac with no neighbors in sight is this modern, contemporary home with everything you could possibly need for a relaxing stay. Enjoy resort-style living at its finest with open plan living, a gourmet kitchen, 5 stylish bedrooms & a glamorous outdoor oasis with salted heated pool, sunbeds, cabanas a basketball court, a playground, pool table & so much more! Amazing designed and decorated home with top High end Furnitures that will Provide you a unique Stay. #miami

22–29 Apr

$1,357 SGD per night

Guest favourite

Home in Palmetto Bay

4.92 out of 5 average rating, 172 reviews

Hamilton House Tropical Oasis in Miami-Heated Pool

Hamilton House Miami is a spectacular tropical oasis, featuring privacy electric gates, 6 bedrooms, 3.5 baths, with a Jaccuzzi in the master. Close to Airport, Cruise Port, South Beach, all hot spots. All rooms have King beds.The house is open concept, featuring a custom kitchen, game room w/Billiards & Dominoes, Ping Pong & high speed Wifi.Heated pool has slide,waterfall & salt filter system which eliminates harsh chlorine. Lots Tiki, fridge, sunbeds, outdoor kitchen, Brazilian BBQ & Smoker.

25 Oct – 1 Nov

$1,014 SGD per night

Superhost

Home in Cutler Bay

5.0 out of 5 average rating, 117 reviews

Amazing Home Miami with Heated Pool & Plays

5 bedrooms / 3 bathrooms 2800 interior sq. ft 11,800 sq. ft Heated pool/Pool Table/Outdoor Kitchen with BBQ/Playground/Basketball Court/Outdoor Dining Table/mini beach/Mega Chess/Mini golf/Foosball/Fire Pit/Sleeps 17 Come enjoy your next vacation in this beautiful modern property. Located in a wonderful and safe area,. The house has a fully equipped kitchen, smart TV in all bedrooms and living room, heated pool for you to enjoy the eternal Florida summer,Visiting Downtown Miami,South beach

28 Sep – 5 Oct

$708 SGD per night

Guest favourite

Home in Homestead

4.93 out of 5 average rating, 358 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.

2–9 Apr

$448 SGD per night

Guest favourite

Guest house in Homestead

5.0 out of 5 average rating, 111 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.

23–30 Aug

$284 SGD per night

Guest favourite

Guest suite in Miami

4.9 out of 5 average rating, 356 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

21–28 Aug

$108 SGD 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.

19–26 Jan

$230 SGD 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.

16–23 Jan

$805 SGD per night

Guest favourite

Home in Miami

4.98 out of 5 average rating, 146 reviews

Beautiful and Spacious 4-Bedroom Heated Pool

Bring your friends and family to this great place with lots of room for fun. Conveniently located near some of south Florida's best attractions, we welcome you and your folks to relax, cook, and swim. Full of fruit trees and green grass, you would never guess that you are just minutes away from the highway. También hablamos español! Escríbanos para más información.

19–26 Jan

$438 SGD per night