Holiday Homes in Southwest Florida

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Southwest Florida

Our top choices for Southwest Florida holiday homes

Siesta Key Island Rentals
322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (46)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
Siesta Key Island Rentals
Siesta Heron Suites & Villas
Condo, Pool View | Private kitchen

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
Siesta Heron Suites & Villas
Top Location w/direct gulf access. Newly renovated kitchen and bathrooms
Terrace/patio

Top Location w/direct gulf access. Newly renovated kitchen and bathrooms

9.8 out of 10, Exceptional, (63)
"This is a great property. Quiet neighborhood which we wanted and yet close enough to everything we needed. Owner is available and helpful and on top of any problem immediately! Well stocked with everything needed. Comfortable beds. Plenty of storage areas for your things!! We were blessed with great weather to enjoy the beautiful lanai! We hope to be back next year to enjoy again!"
Top Location w/direct gulf access. Newly renovated kitchen and bathrooms
Open Water Home with lots of dolphin and manatee sightings. Boat docking.
Dining

Open Water Home with lots of dolphin and manatee sightings. Boat docking.

9.6 out of 10, Exceptional, (133)
"Cozy,calming and a relaxing stay. The outside room was great. Got to see a few dolphins while relaxing outside. We will try and stay there again in the future."
Open Water Home with lots of dolphin and manatee sightings. Boat docking.
Beach pool House Family Vacation Home.
Beach nearby, sun-loungers, beach towels

Beach pool House Family Vacation Home.

9.8 out of 10, Exceptional, (226)
"We had a great time. The house is in a very nice location and the owners were super kind and helpful. The outside space was perfect for enjoying the evenings. "
Beach pool House Family Vacation Home.
Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (238)
"Great Location !!"
Tropical Villas of Venice Beach
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Beach nearby, sun-loungers, beach towels

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

9.8 out of 10, Exceptional, (110)
"The location of this property is excellent! It is walking distance to the beach. The beach is beautiful! It was also very close to Armand Circle where you can find many shops and restaurants. The communication with the hosts was excellent! They were very attentive and responded to any questions in a timely manner. The home is comfortable for a small family. We enjoyed our stay and I would definitely like to return in the future. "
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!
Interior

Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

9.4 out of 10, Exceptional, (3)
"Well maintained propert and enjoyed our stay."
The price is AU$2,097
includes taxes & fees
1 Sept - 2 Sept
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!
Mimosa Bay: Waterfront Oasis w/ Heated Pool, Hot Tub & Bay Views
Property grounds

Mimosa Bay: Waterfront Oasis w/ Heated Pool, Hot Tub & Bay Views

10.0 out of 10, Exceptional, (1)
"Exceptional property! We truly had the most amazing stay. The property is so beautiful and clean. It has a ton of charm, and the view off the entire back of the home of the emerald green bay is unmatched!Between waking up to amazing sunrises, hearing the sound of the water, while enjoying the bay breeze and watching all of the dolphins swim by, it was one of the most serene and tranquil experiences. The pool and spa are brand new and we loved having options to swim in the pool, paddle board...
Mimosa Bay: Waterfront Oasis w/ Heated Pool, Hot Tub & Bay Views
South Seas Bayside Villa 5130: Your Perfect Island Retreat
A heated pool

South Seas Bayside Villa 5130: Your Perfect Island Retreat

8.8 out of 10, Excellent, (15)
"Beautiful apartment "
South Seas Bayside Villa 5130: Your Perfect Island Retreat
3-bedroom vacation home just steps from Periwinkle Way
Fridge, microwave, oven, stovetop

3-bedroom vacation home just steps from Periwinkle Way

2.0 star property
10.0 out of 10, Exceptional, (5)
"Ibis Lane is centrally located- within walking distance of shops, restaurants, and ice cream! The house is spacious and laid out nicely for guests to have their own space. Situated on a dead end street, it’s perfect for kids and dogs. My great niece and nephew had a ball riding their bikes, and visiting “ Cheeburger Cheeburger” to put a quarter in the huge gumball machine. Denise answered all questions and got back to me right away. She also added many thoughtful touches to her home to make...
3-bedroom vacation home just steps from Periwinkle Way
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Beach nearby, sun-loungers, beach towels

Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

9.6 out of 10, Exceptional, (109)
"Awesome location, perfect beach supplies provided, and VERY clean! "
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Siesta Beachfront Paradise: Luxurious Home Steps from Beach with Infinity Pool!
A heated pool

Siesta Beachfront Paradise: Luxurious Home Steps from Beach with Infinity Pool!

10.0 out of 10, Exceptional, (3)
"We loved the house! Great location, beautiful spaces, plenty of room for all of us. Couldn’t have picked a better place for our family to stay for our niece’s wedding! We’d definitely love to stay here again!"
Siesta Beachfront Paradise: Luxurious Home Steps from Beach with Infinity Pool!
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Beach nearby, sun-loungers, beach towels

Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

9.6 out of 10, Exceptional, (134)
"we had a good stay"
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Anna Maria Beach Condo 1/1
Property grounds

Anna Maria Beach Condo 1/1

9.8 out of 10, Exceptional, (183)
"Nice place very roomy easy check in very close to beach and restaurants"
The price is AU$560
includes taxes & fees
24 Aug - 25 Aug
Anna Maria Beach Condo 1/1
Near Bean Point!! Short stays available! Heated Pool
Exterior

Near Bean Point!! Short stays available! Heated Pool

9.6 out of 10, Exceptional, (51)
"Good property with access to the beach "
Near Bean Point!! Short stays available! Heated Pool
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes
On the beach

Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

9.8 out of 10, Exceptional, (119)
"Such a beautiful property! We can't wait to go back!"
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes
Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT
Outdoor pool, a heated pool

Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT

The price is AU$2,131
includes taxes & fees
24 Aug - 25 Aug
Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
On the beach

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (19)
"We had a great stay at this property! We had five adults and one infant with plenty of room to be comfortable. We enjoyed the short walk to the beach and that beach chairs were provided by the HOA (umbrellas are not but there was one at the property). The owners were wonderful, fast responses to any messages and made sure we had everything we needed to have a great time! Definitely recommend this property if you’re in Siesta Key and looking to be very close to the beach!"
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
~NEW! OCEAN VIEW+ ROOFTOP DECK+ SWIMSPA+POOL TABLE +PUTTING GREEN- SLEEPS 14!!!
Property grounds

~NEW! OCEAN VIEW+ ROOFTOP DECK+ SWIMSPA+POOL TABLE +PUTTING GREEN- SLEEPS 14!!!

9.8 out of 10, Exceptional, (11)
"We loved our time here and can’t wait to book it for next year!"
~NEW! OCEAN VIEW+ ROOFTOP DECK+ SWIMSPA+POOL TABLE +PUTTING GREEN- SLEEPS 14!!!
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.
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Top Southwest Florida Hotel Reviews

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

10/10 Excellent
"Everything about this place. We will be back "
Brittany 1-night trip
Posted 11 hours ago
Hyatt Vacation Club at Coconut Cove, Bonita Springs