10 Best Vrbo Vacation Rentals In Midnight Cove, Siesta Key, Florida

Anne
Contributing Writer
Updated
| 5 min read

Midnight Cove is located on the white sands of Crescent and Siesta Beach in Siesta Key, Florida. The resort covers 11 acres of tropical, floral, and lush greenery, along the blue coast of the Gulf of Mexico all the way to Sarasota Bay and the Intracoastal Waterway. There is a choice of staying Gulfside, with beautiful beach views and incredible sunsets, or on the Bayside, looking over the calmer waters of the Bay and the Intracoastal Waterway. The resort features condominiums and townhouse accommodations to suit everyone. Each is individually owned and decorated and offers all the comforts of home and more. There are two communal pools, tennis courts, gas grills, and a fitness center in the clubhouse, as well as boat docks for fishing and pleasure boats. Scroll below to enjoy our top picks of some of the best Vrbo accommodations in Midnight Cove, Siesta Key, Florida.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on August 28, 2025.

1. Two-bedroom condo with private beach (from USD 349)

This new, seventh-floor condo is on the gulf side of Midnight Cove and offers beautiful views over the beach and the Gulf of Mexico. Free Wi-Fi is available throughout. The living area features air conditioning and a TV with satellite or cable channels, while the kitchen has everything necessary for cooking up daily meals. The master bedroom has a king-sized bed, while the second room has two single beds. Two bathrooms are available.

Siesta Key, Florida, United States

792 meters (0.5 ft) from Siesta Key Watersports
condo 4 Guests 2 Bedrooms 2 Bathrooms

2. Lovely flat with private beach access (from USD 328)

This beachfront condo is ideal for families and offers a 180-degree view of the Gulf of Mexico and Crescent Beach. There is a screened lanai on which to relax and watch the sunset. The living area has a flat-screen TV with DVD, stereo, and DSL internet connection. The kitchen is newly remodeled with everything a chef could ask for. The master bedroom features a queen-sized bed and a TV as well as a bathroom with bathtub and shower. The guest bedroom has two twin beds and access to a half-bath.

Siesta Key, Florida, United States

790 meters (0.5 ft) from Siesta Key Watersports
PRIVATE VACATION HOME 4 Guests 2 Bedrooms 1 Bathroom

Top guest reviews
Host:
Well maintained easy to get around nice amenities
Read more reviews

3. Two-bedroom condo with private beach (from USD 202)

This attractively decorated condo is located on the second floor and has been newly remodeled. The living area is spacious and comfortable overlooking the canal front. There is a separate den off the living room and an enclosed lanai with sliders to let in the ocean breezes. The kitchen comes well-equipped and there is a washer and dryer available. The master bedroom features a king-sized bed and there are two single beds in the second bedroom. There is a further sofa bed in the living area, sleeping up to six guests in total. Free WiFi is available throughout.

Siesta Key, Florida, United States

479 meters (0.3 ft) from Siesta Key Watersports
PRIVATE VACATION HOME 4 Guests 2 Bedrooms 1 Bathroom

Top guest reviews
Location:
Nice clean and updated property in a great location
Amenities & Room:
More than I expected Very comfortable Relaxing view of canal
Read more reviews

4. Two-bedroom unit on the Gulf side of Midnight Cove

This spacious condo is just a few steps from the white sands of Siesta Key Beach and perfectly located close to all the shops and restaurants in the area as well as fishing and watersports. The condo has a spacious living area and fully equipped kitchen with everything necessary to cook daily meals. The master bedroom features a king-sized bed and a walk-in shower, while the guest bedroom has one full-size bed and one single bed, with a separate bathroom with shower.

Siesta Key, FL, US

790 meters (0.5 ft) from Siesta Key Watersports
9 reviews  
condo 6 Guests 2 Bedrooms 2 Bathrooms
Top guest reviews
Host:
some additional updating/repairs would make it even better
convenient and no hassles with rental process
we had the unique opportunity of going inside another unit in the building (other family was staying there too) and they had practically nothing compared to ours
we also found sand toys, bags, floats in closet which was a nice surprise and would be great for younger kids
the balcony had great furniture, drying rack for suits and towels, and a beautiful new floor
Location:
it is also a short walk for groceries, restaurants and bars
thankfully, we were not too close to the overcrowded siesta key village
great relaxing place to stay
great location and beautiful condo for our family of 4 1/2
the complimentary beach chairs and umbrellas were a great bonus at midnight cove
Cleanliness:
it was homey, bright, and we can't say enough about the 2 views of the ocean and pool
the bathrooms have updated walk-in showers and the master bath overlooks the pool and ocean too
Amenities & Room:
new refrigerator and microwave in the kitchen
it is right on the beach and directly over the pool
the 2-bedroom condo was just the right size for our 4-person family
more than enough towels, bedding, pillows
the use of the included pack n play was a bonus!! felt like home
Read more reviews

5. Lavish condo with Intracoastal water views and private beach

This third-floor two-bedroom condo is a corner unit and overlooks the Intracoastal Waterway, a short walk from a private section of Crescent Beach. There is a screened lanai overlooking the view. The living area features a 37-inch (94-cm) flat-screen TV and DVD player and a comfortable sofa bed. The kitchen comes equipped with all modern appliances. Free Wi-Fi is available throughout. The master suite has a king-size bed and a TV, opens onto the lanai and has an en-suite bathroom. The second bedroom features twin beds and a TV and there is a guest bathroom with bathtub and shower combination.


328 meters (0.3 ft) from Siesta Key Watersports
24 reviews  
condo 6 Guests 2 Bedrooms 2 Bathrooms
Top guest reviews
Host:
We would love to return next year to experience the beautiful beach
It was well equipped and the owner was fast about responding to any questions
Unfortunately we arrived during red tide
However I would only have one criticism
We made thanksgiving dinner and only had to purchase food
Location:
The location was also quiet
We've stayed in many places in the Sarasota/Siesta Key area and Midnight Cove is by far our favorite
Condo was spotless and we enjoyed the location- short walk to beach shopping and restaurants
We sat on the porch and enjoyed the dolphins swimming by
We've also rented multiple places in Midnight Cove and MC 2 and this tops them
Cleanliness:
It was very clean and comfortable for a family of 4
I look forward to returning again
Amenities & Room:
The only room where it is not noticeable (fortunately) is the master bedroom
The owners have thoughtfully stocked this condo for comfort from the kitchen to the beach
My younger daughter loved the little room off the kitchen
It was a great vacation - in part because of the condo
The large lanai was great for sitting and enjoying the bay with a cup of coffee
Read more reviews

6. Seventh-floor condo overlooking Crescent Beach

This modern two-bedroom condo offers a spectacular view over the ocean from the spacious lanai which stretches from the condo’s living area to the master bedroom. Enjoy views of the white sands and the Gulf of Mexico. The living area features leather sofas and a flat-screen TV with DVD. There is a modern and well-equipped kitchen offering stainless steel appliances. Free WiFi is available throughout the condo and there is an unlimited long distance telephone service. The master bedroom features a king-sized bed and full bathroom, while the guest bedroom has two full-size beds and a TV and DVD. There is also a guest bathroom with a walk-in shower.

6342 Midnight Pass Road 476

790 meters (0.5 ft) from Siesta Key Watersports
62 reviews  
condo 6 Guests 2 Bedrooms 2 Bathrooms

7. Gulf-front Midnight Cove condo

This attractive two-bedroom condo is located on the fourth floor in the Midnight Cove condo community, right on Crescent Beach. The condo has a screened lanai spanning the front of the property and overlooking the white sands. The living area features a flat-screen TV and DVD player and the master suite also features a TV and private bathroom. There is a fully equipped and spacious kitchen and open plan living area. The master bedroom has a king-sized bed while the guest bedroom features a double bed, two single beds, and bunk beds, with a family bathroom available.


790 meters (0.5 ft) from Siesta Key Watersports
62 reviews  
condo 6 Guests 2 Bedrooms 2 Bathrooms

8. Townhouse with private beach

This modern and spacious two-bedroom townhome overlooks the boat basins and the canal and is set across the street from Siesta Beach. The newly refurbished living room features a 55-inch (139.7-cm) SMART TV and a comfortable sofa bed. The kitchen has also been renovated with all-new appliances and there is a toilet on the main floor. Free WiFi is on offer throughout the property. There are two lanais on the property, one in front of the living area and the second off the master bedroom upstairs. The master features a king-sized bed and flat-screen TV with its own shower, while the second bedroom has twin beds and a bathroom with bathtub and shower combination. The unit is close to one of the community pools and convenient to all the amenities.


566 meters (0.4 ft) from Siesta Key Watersports
33 reviews  
townhome 6 Guests 2 Bedrooms 3 Bathrooms
Top guest reviews
Host:
the beach was absolutely awesome
and we really had no problems having vehicles stop for us
We recommend highly the resort the beach and the wonderful sun
We didn't use the pools tennis court or the clubhouse
but they also seemed well maintained
Location:
Beach is a few minutes walking distance
The unit was in a great location - an easy walk to the beautiful Siesta Key beach and area shops
This townhouse is in a perfect location for lots of fun
Townhouse was in a great location to restaurants beach and pool
Siesta Key is a wonderful vacation area and Midnight Cove is what we were looking for
Cleanliness:
It was very clean and comfortable
The condo was very clean and was furnished with everything we needed
The condo is absolutely gorgeous and clean very nicely decorated
Amenities & Room:
the private beach access with chairs/umbrellas was great
There was plenty of room for the four of us not to be on top of each other
The kitchen was spacious and well stocked with everything you need
The property itself was wonderful and the condo was AWESOME
It was great to have lounge chairs and umbrella at the beach already set up
Read more reviews

9. Family townhome on Siesta Key

This lovely townhome is located on Siesta Key and offers unlimited access to Crescent Beach. The spacious living room, with a TV with satellite or cable channels, opens onto an enclosed lanai and a dining room and there is also a fully equipped kitchen. On the upper level, there is a laundry room and open lanai off the master bedroom which features a queen-sized bed. The second bedroom has twin beds and there are two aero beds available, plus a sofa bed in the living area and a Porta-crib, making the townhome ideal for a family vacation. The property is air-conditioned and free WiFi is available throughout.

Sarasota, Florida, United States

472 meters (0.3 ft) from Siesta Key Watersports
PRIVATE VACATION HOME 6 Guests 3 Bathrooms

Top guest reviews
Host:
We absolutely loved our unit and the Midnight Cove complex and have found our new home away from home
so we were somewhat hesitant about trying something new
Can not wait to come back again
We are creatures of habit usually staying at the same complex every year
Location:
We have stayed in this condo for severalyears now and it is always impeccable
The home is convenienly positioned between the bench on the inland waterway for a leisurly read and great boat watching the heated pool and the sands of Siesta beach and easy walk to great restaur...
Amenities & Room:
The condo itself is nicely furnished - we are cooks and the kitchen has all the conveniences of home great lighting and whole place is easy to maintain
I also like that they just put in a new 40inch flat screen TV
Read more reviews

10. Penthouse right on the water

This luxurious and spacious penthouse condo is located on the Intracoastal Waterway in a gated complex, a five-minute walk from the beach in Siesta Key and with private beach access. The penthouse is on the fifth floor with an elevator and offers breathtaking water views from three sides of the condo. There is a screened lanai with sliding windows facing the bay, accessible from both the living area and master bedroom. The living area features an entertainment center with a flat-screen TV with cable channels, AM/FM stereo, and a DVD/VCR. The kitchen comes equipped with modern appliances for daily cooking and there is a washer and dryer available. Internet connection is available for guests. The master bedroom features a king-sized bed, while the second has two single beds.

Siesta Key, Florida, United States

960 meters (0.6 ft) from Siesta Key Watersports
condo 4 Guests 2 Bedrooms 2 Bathrooms

Top guest reviews
Host:
the owner was real easy to work with too
Location:
great breakfast place too
there is a good choice of golf courses close by too
some are within walking distance - our favorite was at the marina just across the bridge
Cleanliness:
condo was very clean roomy and beautifully furnished
it is very spacious and clean
fantastic stay at this beautiful clean comfortable condowith all the amenities
the condo was clean well furnished and had everything we needed for a week vacation
it’s very clean and has a nice open living room and dining area
Amenities & Room:
the decor of the condo is light and airy and was so comfortable
Read more reviews

Enjoy the magic of Siesta Key

Whether relaxing on the sand, boating, or fishing, make Crescent Beach your home in a condo or townhome, while staying in comfort and style in one of the best Vrbo accommodations in Midnight Cove, Siesta Key, Florida, USA.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Anne Sewell was born in England, but has spent most of her life in Africa - Malawi, Zimbabwe and South Africa - and now resides on the beautiful Costa del Sol in southern Spain. She loves writing...View profile

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