Southwest Florida Holiday Rentals

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Holiday Rentals in Southwest Florida

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, (557)
"Rooms and view were beautiful"
The price is NZ$328
per night
16 Jun - 17 Jun
The Suites at Fishermen’s Village- 2 Bedroom Suites
Edison Beach House
3.5 star property
9.4 out of 10, Exceptional, (1084)
"It was everything promised and we will stay here again, soon!! "
The price is NZ$377
per night
2 Jun - 3 Jun
Edison Beach House
Bellasera Resort
4.0 star property
9.6 out of 10, Exceptional, (1930)
"This is second time we stayed at this property and i absolutely love it"
The price is NZ$451
per night
2 Jun - 3 Jun
Bellasera Resort
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Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2004)
"Very convenient for a big group The room was clean and the property has a great location close to siesta key you can even make it walking and also it’s close to restaurants and stores Just the pool needs a little bit of attention I think The rest was great"
The price is NZ$261
per night
2 Jun - 3 Jun
Hibiscus Suites - Gateway to Siesta Key
Wiggins Pass Chalet
4.0 star property
9.6 out of 10, Exceptional, (134)
"Great apartment style hotel. The only downfall, there's no pool or jacuzzi. That would've made it absolutely perfect."
The price is NZ$275
per night
2 Jun - 3 Jun
Wiggins Pass Chalet
Hyatt Vacation Club at Coconut Cove, Bonita Springs
4.0 star property
9.2 out of 10, Wonderful, (405)
"nice place"
The price is NZ$466
per night
4 Jun - 5 Jun
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Park Shore Resort
3.0 star property
8.8 out of 10, Excellent, (703)
"Lots of construction going on. Not advised that our balcony would be unavailable during our stay."
The price is NZ$379
per night
3 Jun - 4 Jun
Park Shore Resort
Kon Tiki Inn
2.0 star property
10.0 out of 10, Exceptional, (114)
"There was nothing to dislike about Kon Tiki. Property is well kept, very clean, updated and maintaince. "
The price is NZ$243
per night
3 Jun - 4 Jun
Kon Tiki Inn
Marco Beach Vacation Suites
3.5 star property
8.0 out of 10, Very good, (712)
"Excelente "
Marco Beach Vacation Suites
Lovers Key Resort
3.0 star property
8.8 out of 10, Excellent, (931)
"Enjoyed the facility Area is still in recovery from Ian. Dining in area wasvery limited"
The price is NZ$529
per night
2 Jun - 3 Jun
Lovers Key Resort
Lazy Cuckoo Inn
3.5 star property
8.8 out of 10, Excellent, (126)
"Very clean and peaceful. I highly recommend this company for vacation rental"
Lazy Cuckoo Inn
Tiny House Siesta
2.0 star property
8.2 out of 10, Very good, (132)
"Came to siesta keys for the first time, really enjoyed our time there and it was a beautiful tiny place"
The price is NZ$289
per night
25 Jun - 26 Jun
Tiny House Siesta
Tropical Villas of Venice Beach
3.5 star property
9.6 out of 10, Exceptional, (192)
"They were so accommodating at Tropical Villas. As part of your stay you had beach chairs, beach umbrella, cooler, coffee pods, sand sifter, beach towels (all in your villa). On-site you have access to use bicycles and washer n dryer at no extra charge. The Elite Villa we stayed in had direct access to the enclosed bug free pool. Our room was extremly clean and reminiscent of old school Florida cottage. The grounds were lush and they even had a sweet little wild brown bunny who wondered around...
Tropical Villas of Venice Beach
GullWing Beach Resort
3.5 star property
9.6 out of 10, Exceptional, (871)
"It's basically a condo you're staying in with all the amenities of home."
GullWing Beach Resort
GreenLinks Golf Villas at Lely Resort
3.0 star property
9.4 out of 10, Exceptional, (487)
"Everything in the hotel was perfect. We loved the experience "
GreenLinks Golf Villas at Lely Resort
IMG MEMORIAL DAY & SUMMER DISCOUNTS! AMI White Sand Beaches/Pickle Ball/GOLF/FUN
10.0 out of 10, Exceptional, (6)
"The house is absolutely beautiful. 4 bedrooms, 3 bathrooms (2 ensuite), well stocked , very nice lanai, big backyard, gas grill, the owner came right away when there was a small issue - she is Very nice. I would highly recommend this house to anyone who wants a beautiful place to stay. Looking forward to staying there again."
The price is NZ$990
per night
14 Jun - 15 Jun
IMG MEMORIAL DAY & SUMMER DISCOUNTS! AMI White Sand Beaches/Pickle Ball/GOLF/FUN
Venice Beach Villas
3.0 star property
9.4 out of 10, Exceptional, (375)
"Pleasantly surprised at how they’ve thought of everything you might need for a stay at the beach. The room was spotless and the grounds nicely planted and maintained. Our new Venice spot to stay."
Venice Beach Villas
Marriott's Crystal Shores
3.5 star property
9.2 out of 10, Wonderful, (202)
"Muy bueno "
The price is NZ$1,740
per night
2 Jun - 3 Jun
Marriott's Crystal Shores
Holiday Inn Club Vacations Sunset Cove Resort, an IHG Hotel
4.0 star property
9.8 out of 10, Exceptional, (215)
"Loved the transportation between hotel and the beach. Providing a cooler and beach chairs a plus."
Holiday Inn Club Vacations Sunset Cove Resort, an IHG Hotel
Charming 3 Bedroom 2 Bath Home with Pool Just 2 Minutes from Anna Maria Island
9.2 out of 10, Wonderful, (11)
"Had fun vacation and great place to stay"
Charming 3 Bedroom 2 Bath Home with Pool Just 2 Minutes from Anna Maria Island
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See all available properties in Southwest Florida
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Southwest Florida you may be interested in

Kompose Boutique Hotel
3.0 star property
9.0 out of 10, Wonderful, (3428)
"This is my third or fourth time staying at this hotel. I enjoy the service and hospitality. The only thing that might be looked down on is that there is not much water pressure in the showers. So showers do take some time when you are getting ready. Otherwise the pool is never packed and the breakfast is good too. "
The price is NZ$183
per night
11 Jun - 12 Jun
Kompose Boutique Hotel
Hyatt Regency Sarasota
4.0 star property
8.2 out of 10, Very good, (1007)
"I enjoyed my stay at this hotel from the staff to the amenities, the pool, restaurant and the comfortable room. My only issue was the elevators. They were extremely slow and very small considering most people had luggage with them. Everything else was wonderful!"
The price is NZ$294
per night
9 Jun - 10 Jun
Hyatt Regency Sarasota
The Westin Sarasota
4.0 star property
8.8 out of 10, Excellent, (1007)
"Stayed one night and it was great. Staff helpful and courteous."
The price is NZ$386
per night
10 Jun - 11 Jun
The Westin Sarasota
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Southwest Florida holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Southwest Florida. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Southwest Florida. Seeing all the best attractions is bound to make you fall in love with Southwest Florida. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Southwest Florida short-term rentals, that won’t be hard to do.

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