Photo by Graciela Arena
Midtown holiday rentals
We found 1,846 holiday rentals — enter your dates for availability
Discover a selection of 36 homes and other holiday rentals in Midtown that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a pool. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Find spaces that suit your style
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Condo/Apartment
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Find the best place to stay - Midtown
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
125 reviews(125 reviews)
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
287 reviews(287 reviews)
Ultimate Beach Adventure! Pool, Restaurant, Bar, Bike Rental, Gym,
Sleeps 3 · 1 bedroom · 1 bathroom
8.08.0 out of 10
Very goodvery good
50 reviews(50 reviews)
Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
180 reviews(180 reviews)
Casa Atlantica: A studio condo on the Atlantic shore of Key West
Sleeps 2 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
153 reviews(153 reviews)
**NATURES EDGE @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
150 reviews(150 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental accommodation in Midtown?
Based on our research, houses are the most popular holiday property type in Midtown. But that goes without saying, everyone’s idea of an awesome trip differs. Vrbo has holiday rentals with every shape, size and budget in mind, and we’ll help you find the perfect fit for you.
How much does it cost to rent a holiday rental in Midtown?
The average price for a holiday rental in Midtown is based on a number of factors, including season, property type and length of stay. Whether you’re looking for a sprawling house with room for friends and family or a cosy cabin for just you and your sweetheart, just add your dates of travel to see stays that offer great value.
How much does it cost to rent a beach house in Midtown?
The average price for a holiday home by the beach in Midtown depends on when you’ll be there and the style and size of property you want. You can quickly and easily find prices on Vrbo by entering your preferred travel dates and destination. Then use the handy filters to pick the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday rentals in Midtown?
Good news! Yes. You’ll have your pick of 34 holiday rentals that cater to pets in Midtown. Plenty of our pet-friendly holiday rentals even have space outdoors for your fur child to have fun in, complimentary treats, doggie beds and proximity to parks or green space. Apply the “Pets allowed” filter to find a pad that’ll set tails wagging on Vrbo.
Can I rent a house with a pool in Midtown?
Check the “pool” box in our handy filter tool and take your pick of 28 houses with private pools in Midtown on Vrbo. Gentle soak, ball games or noodle joust? Leisure time is your call when your holiday property comes with a swimming pool.
What are popular rental amenities in Midtown?
When it comes to rental amenities that people search for in Midtown, a water view, a barbecue grill and an ocean view are the most popular. With Vrbo holiday homes, there are choices to match your style and taste, whether you’re travelling with friends, family or even pets.
Are there large group holiday rentals in Midtown?
With three holiday rentals that can sleep 10 guests or more in Midtown, there’s no need to limit the invite list. From holidays with the extended family to events like anniversary parties and weddings, Vrbo can help you find a large group rental to suit the occasion.
Are there holiday rentals in Midtown that welcome kids?
With 34 family-friendly holiday properties to select from in Midtown, now is a great time to introduce your children to the excitement of travel. Just check our “Properties good for families” filter to search for stays that feature amenities ideal for families on the move, like full kitchens, yards, entertainment areas and bunk beds.
What are the top attractions for families in Midtown?
Keep the kids happy at these fabulous family-friendly attractions in Midtown:
- Smathers Beach
- South Beach
- Higgs Beach
Are there one-bedroom holiday rentals in Midtown?
There are three one-bedroom properties in Midtown to choose from. A one-bedroom holiday property is an excellent choice if it’s only you and your partner or if you’re flying solo. Throw in more privacy, convenience and space compared to a hotel, and you’ve got the makings of an unforgettable trip.
Can I find two-bedroom holiday rentals in Midtown?
Take off with your besties and enjoy peace, privacy and comfort in one of the nine two-bedroom holiday homes Midtown has to offer.
Are there holiday rentals with WiFi in Midtown?
Whether you want to stay in touch with world events, make a video call or surf social media, there are 11 holiday homes with WiFi in Midtown. Check the “WiFi” box when searching on Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Midtown?
Midtown has 32 holiday rentals where you’ll be able to relax in air-conditioned comfort. To book a stay on Vrbo that features this amenity, enter your desired travel dates and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a holiday rental in Midtown?
The minimum required age is generally 16, 18 or 21. It can change from property to property on Vrbo, so check the rules of your preferred Midtown stay before booking your escape.
How long can I rent a holiday rental in Midtown for?
How long you can book a holiday rental in Midtown is down to the property. Simply enter your chosen travel dates to display a list of options offering extended stays. With loads of creature comforts like washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you’re sure to get a terrific place to call your home away from home in Midtown.