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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.

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Home in Cutler Bay

4.82 out of 5 average rating, 226 reviews

Andy Resort Inc-Flash Sale

ANDY RESORT.inc is very good for couples, business travelers, tourist, family vacation... Upon arrival a representative will receive you to give you a pleasant welcome and a short tour of the installation. The installation has a majestic FULL PRIVATE POOL and fabulous waterfall In its extensive pool area also has beautiful bar, barbecue, firepit, a place to relax and feel disconnected from stress. Around the resort there are several shops, restaurants, attractions, cinemas, bakery, super market

Home in Cutler Bay

4.96 out of 5 average rating, 102 reviews

Double King Home by the Bay FAST WI-FI & Coffee

Whether you are visiting the Florida Keys, the beaches of Miami, or looking for a comfortable staycation, discover what South Florida has to offer while feeling at home. This home is located near Southland Mall, The Falls Shopping Center, Black Point Marina, and Miami Metro Zoo. Guests will be centrally located and will be within: ❧ 48 minutes from the Florida Keys. ❧ 37 minutes from Miami Beach. ❧ 33 minutes from the Everglades. Bring the whole family and enjoy our fast Wi-Fi and Free Coffee.

Tiny home 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.

Guesthouse in Miami

4.97 out of 5 average rating, 182 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.

Tiny home in Cutler Bay

4.98 out of 5 average rating, 193 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.

Home in Cutler Bay

4.97 out of 5 average rating, 139 reviews

Luxe Escape Miami 5BR Heated Pool/ Plays, BB court

5 bedrooms / 3 bathrooms 2552 interior sq. ft 11,800 sq. ft Heated pool, Pool Table, Outdoor Kitchen with BBQ, Playgroun, Half Basketball Court, Outdoor Dining Table, mini beach, Mega Chess, Mini golf, Foosball, Fire Pit 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

Guest suite in Miami

4.89 out of 5 average rating, 342 reviews

Guestsuit- Exterior Entrance, SelfCheckin.

If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Place 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 -Swimming Pool -Central A/C -Ceiling fan -Kitchenette -Refrigerator -Microwave -Coffee maker -Netflix-HBO TV -Ceramic Tile Floors -Full Closet -Towels/Bath essentials -Iron & Board

Home in Homestead

4.93 out of 5 average rating, 376 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.

Home in Miami

4.95 out of 5 average rating, 113 reviews

2K beds, Fire Pit,spa shwr, otdr ktch by Hwy exit

Fire pit Heated Pool. Surround sound systems. Creative spaces with wall murals. Front gate, pvt prkng. Fiber optic WI-FI. Indoor and outdoors kitchens-Stainless steel appliances. Self check in. 4/2 w/smart TVs in all bdrs: 2 kings, queen & 2 double beds. Master bath w/spa like shower. Crib, playpen, highchair, indoor gate and infant car seat provided. Quiet established neighborhood. Starter kit of dishwasher detergent, trash bags, toilet paper, paper towel. Laundry detergent not provided

Guest suite in Cutler Bay

4.78 out of 5 average rating, 288 reviews

Private Waterfront Studio Paradise

Casa Cocos is a private studio, with a private entrance, bathroom and kitchenette, and free and secure parking. It is nestled in Florida's tropical waterfront paradise. Come enjoy the views of the garden, go for a swim, paddle board, canoe, kayak, grill, take a nap in a hammock, and just relax. Casa Cocos is surrounded by nearby restaurants, bars, retail stores, malls all within walking distance or a short drive. 30 minutes to airport, downtown, South Beach, Keys, and Everglades.

Home in Miami

4.96 out of 5 average rating, 161 reviews

Miami Getaway - Heated Pool, BBQ, Washer & Dryer

Be our guest and have a wonderful stay in this beautiful Miami home designed to create great memories. 3 bedrooms 2 bathrooms with enough space to sleep 10 guests. Heated pool to enjoy even during winter season. Conveniently located within a short distance from all of Miami's main attractions. Restaurants, shopping malls, nightclubs, bar/pubs, art centers, bicycle trails, beautiful parks and bay views between 5 - 10 minutes away. Only 50 minutes away from the Florida keys.

Home in Miami

4.96 out of 5 average rating, 346 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.

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Popular amenities for Cutler Bay rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Miami

4.87 out of 5 average rating, 177 reviews

Heated pool Spacious home 18 miles to Mia Airport

Home in Miami

4.95 out of 5 average rating, 40 reviews

Family retreat oasis, heated pool, jacuzzi & grill

Home in Cutler Bay

4.82 out of 5 average rating, 66 reviews

Heated Pool/Jacuzzi Paradise: Cozy Miami Retreat

Home in Cutler Bay

5 out of 5 average rating, 20 reviews

Group Favorite: Pool, Fire Pit, Beach & Basketball

Home in Hollywood

4.96 out of 5 average rating, 197 reviews

Hollywood Sunshine Resort Pool House w/ Hot tub

Home in Miami

4.98 out of 5 average rating, 108 reviews

Encanto Family, cozy heated pool, center of Miami

Home in Cutler Bay

5 out of 5 average rating, 13 reviews

Canal front, 2 King Beds, Pool, Game Room

Home in Homestead

4.86 out of 5 average rating, 7 reviews

Farmhouse Oasis Magical Retreat in Redlands Miami!

Condo rentals with a pool

Condo in Mid Beach

4.92 out of 5 average rating, 181 reviews

Newly Renovated - Fontainebleau Tresor 1 Bedroom

Condo in South Beach

5 out of 5 average rating, 155 reviews

W Hotel - 1B Residence w/Ocean View

Condo in Hollywood Beach

4.88 out of 5 average rating, 146 reviews

Ocean Seaside, gated and tranquil vacation home.

Condo in Mid Beach

4.96 out of 5 average rating, 149 reviews

Fontainebleau Jr. Suite King Bed with Ocean Views.

Condo in Doral

4.86 out of 5 average rating, 132 reviews

Modern and comfortable Studio In Downtown Doral

Condo in Sunny Isles Beach

4.93 out of 5 average rating, 122 reviews

Stunning direct ocean front 2 bed / 2.5 bath condo

Condo in Mid Beach

4.92 out of 5 average rating, 129 reviews

Fontainebleau Sorrento Jr. Suite w/ Balcony

Condo in North Bay Village

4.87 out of 5 average rating, 257 reviews

Gorgeous studio with water & downtown view.

Home rentals with a private pool

Home in Hollywood

New place to stay

Casa Lucia 5br Home W/ Pool Near Hard Rock Casino

Quick stats about vacation rentals with a pool in Cutler Bay

Total rentals
60 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

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