Southwest Florida Vacation Rentals

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Browse Select Southwest Florida Vacation Homes

Tropical Villas of Venice Beach
3.5 star property
9.6 out of 10, Exceptional, 197 reviews
"Beautiful property well takien car of qnd very convenient the property manager tonya goes out of her way to make the stay qn great experience "
Tropical Villas of Venice Beach
Villa Margarita - 4 Bedroom w/ Beautiful Lake View and Gulf Access!
10.0 out of 10, Exceptional, 9 reviews
"House was perfect for all of us to find our happy spots. Pool, hot tub, waterside, shady seats -- all used. Sunsets were great and walked daily to Rotary Park for fun or weekend activities. Area and house are still being rebuilt from Hurricane, but it didn't hamper us much (one nearby restaurant was still closed). Recommended!"
Villa Margarita - 4 Bedroom w/ Beautiful Lake View and Gulf Access!
Charming 3 Bedroom 2 Bath Home with Pool Just 2 Minutes from Anna Maria Island
9.0 out of 10, Wonderful, 14 reviews
"Great location and super close to the Beach. If you want a less busy beach go south to long boat keys."
Charming 3 Bedroom 2 Bath Home with Pool Just 2 Minutes from Anna Maria Island
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LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...
9.4 out of 10, Exceptional, 26 reviews
"The apartment was very clean and comfortable. So many interesting photos and books. The layout of the apartment was comfortable, spacious and cosy at the same time. Very quiet area. Very close to the beach. I would definitely stay there again. Communication with owner was quick and easy."
The price is CA $172
CA $673 total
includes taxes & fees
Jun 22 - Jun 23
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...
Bay House Retreat managed by Beach Retreats
9.8 out of 10, Exceptional, 43 reviews
"Went to Sarasota for Graduation. Perfect home for 3 generations of family to stay. Beautiful property on a baby peninsula into the bay, island right across the way where birds came to roost for the night. Lovely to just sit and watch the bay, but also awesome pool and really enjoyed adding pontoon boat rental. Able to cook most meals at home. Great location for accessing Sarasota and Bradenton schools/restaurants/beaches but also didn’t have much desire to leave the house."
Bay House Retreat managed by Beach Retreats
Villa 1, Spacious, Hot Tub, Saltwater Htd Pool 136 reviews
10.0 out of 10, Exceptional, 140 reviews
"We loved the property, especially pool, hot tub, bikes and kayaks. We would book this house again."
Villa 1, Spacious, Hot Tub, Saltwater Htd Pool 136 reviews
Pet friendly renovated duplex 5 min drive from the beach
10.0 out of 10, Exceptional, 19 reviews
"Clean, cute, plenty of beach towels, quiet neighborhood. I would stay here again."
Pet friendly renovated duplex 5 min drive from the beach
Renovated snowbird-friendly home with private heated pool, pool spa, gas grill
9.0 out of 10, Wonderful, 28 reviews
"This house is perfect for a vacation, or even a weekend getaway! Great location, safe ! House has a lot of great features! We will definitely stay there again!"
Renovated snowbird-friendly home with private heated pool, pool spa, gas grill
Cozy Cottage - Steps to Riverwalk/Close to Beaches
10.0 out of 10, Exceptional, 143 reviews
"Fantastic ! We needed a place for a couple nights while we had a home repair done to our house. (we live in Bradenton). Very cozy & homey feeling. Super clean & very well set up for a long stay if needed. Fully equipped kitchen with every thing you need from a slow cooker to a blender. And everything in between. Will definitely stay again if needed. Bradenton's real hidden Gem! Super comfy bed, and nicely furnished. Thank you it was wonderful! "
Cozy Cottage - Steps to Riverwalk/Close to Beaches
Coral Cove: Walk to the Beach! Heated pool! Prime North End!
10.0 out of 10, Exceptional, 28 reviews
"It was an easy process, great location and well stocked house! Would definitely stay again."
Coral Cove: Walk to the Beach! Heated pool! Prime North End!
Vibrant Island Home w/ Pool, 1 Block to Beach
9.6 out of 10, Exceptional, 29 reviews
"Wonderful place to stay. Very close to beach and walking distance to plenty of shops and restaurants."
Vibrant Island Home w/ Pool, 1 Block to Beach
Three block walk to beach, private pool, designer home
10.0 out of 10, Exceptional, 175 reviews
"The property was very clean and met all of our needs. Plenty of room for up to six people. Having a pool onsite was a great option if we didn’t feel like walking to the beach, and access to a washer/dryer was a very nice perk. The host was extremely responsive prior to and during our stay."
Three block walk to beach, private pool, designer home
Beach Entry Heated Pool & Hot Tub!
10.0 out of 10, Exceptional, 35 reviews
"Loved our stay at this property. Pool and hot tub were amazing! The lanai was so wonderful with the ceiling fan which made it bearable with the hot weather. The house was comfortable and clean and the living room furniture was so comfortable, my mom loved it and spent most of her time there watching TV. The pool was so amazing during the day and night! Thank you for all the amenities. Just one thing was missed. There was no iron or ironing board but other than that everything was so comfortable...
Beach Entry Heated Pool & Hot Tub!
Oceanview 3-bdrm home steps from beach! Heated pool & hot tub. Sleeps 8.
9.2 out of 10, Wonderful, 30 reviews
"Jen and Kevin's home was amazing and just what we needed for a long weekend get away with family and friends. The pool and downstairs patio were great after afternoons on the beach. They are super responsive, and let us check in early and out late. We would definitely look to book again next time we visited the area."
The price is CA $584
CA $1,244 total
includes taxes & fees
Jun 29 - Jun 30
Oceanview 3-bdrm home steps from beach! Heated pool & hot tub. Sleeps 8.
Blue Lagoon North by SeaBreeze Vacation
9.8 out of 10, Exceptional, 24 reviews
"Very nice and clean. Fully equipped with beach cart and umbrellas"
Blue Lagoon North by SeaBreeze Vacation
Cozy beach getaway! Close to Siesta Key Beach! Pet Friendly!
8.8 out of 10, Excellent, 20 reviews
"Property was very nice, perfect for our trip. Had a nice lay out well decorated confortable. Very close to the beaches and stores. The only things were that the laundry room and kitchen had a strong musky smell and the hot tub was dirty with residue."
The price is CA $275
CA $435 total
includes taxes & fees
Jun 20 - Jun 21
Cozy beach getaway! Close to Siesta Key Beach! Pet Friendly!
Panoramic Gulf Access - Heated Pool - Screened Lanai -Triple Size Lot - Quiet St
9.8 out of 10, Exceptional, 36 reviews
"My hunt for our vacation place had both my dog and my youngest wishes grandson in mind. My grandson wanted so bad to have a pool and my Labrador just wanted to tag along. I found this house and instantly fell in love with it. It had everybody’s wish list in mind. I wanted to be able to have a peaceful and relaxing vacation. This beautiful house is right on the canal so I was able to rent a boat for 4 days which was amazing. We were able to boat to several beaches and boat throughout the canals....
Panoramic Gulf Access - Heated Pool - Screened Lanai -Triple Size Lot - Quiet St
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, 160 reviews
"Everything I wanted for a vacay! Nice views nice home and everything we need was there!"
The price is CA $619
CA $1,302 total
includes taxes & fees
Jul 2 - Jul 3
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak
10.0 out of 10, Exceptional, 97 reviews
"This was our 2nd year staying at Rum Cove and we would definitely book this house again. The property managers were very responsive to one minor issue that we had on check in. The house is in walking distance to the beach, the pier and many restaurants and shops."
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak
Tropical Paradise ~ enclosed heated pool with built in spa
9.8 out of 10, Exceptional, 36 reviews
"We enjoyed our stay! Relaxing and quiet. We had everything we needed and loved our time together here!"
Tropical Paradise ~ enclosed heated pool with built in spa
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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 property types in Southwest Florida

The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0 star property
9.8 out of 10, Exceptional, 573 reviews
"The room was wonderful, beautiful views of the bay and beach. However the floors were filthy. Management needs to hire a tile cleaning company to professionally clean the floors. The dust mop method used by the hotel staff does not work. If you walk aroung barefooted in the room your feet WILL become black."
The price is CA $221
CA $248 total
includes taxes & fees
Jun 23 - Jun 24
The Suites at Fishermen’s Village- 2 Bedroom Suites
Bellasera Resort
4.0 star property
9.6 out of 10, Exceptional, 1,940 reviews
"Excelente atención. Instalaciones muy agradables y pulcras. El único detalle fue que por salir apresurada a la playa dejé mi cadena con baño de oro en un cajon del baño, cuando regresamos ya habían hecho la limpieza y mi cadena ya no estaba. No deje tip para room service puesto que la persona ya se había cobrado. Una lástima que la gente no valore su trabajo y se expongan a ser despedidos. El hotel es excelente, sin duda volveré por tercera vez. "
The price is CA $361
CA $438 total
includes taxes & fees
Jun 23 - Jun 24
Bellasera Resort
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, 2,013 reviews
"El hotel está en un lugar bien asequible. Pero se necesita que le dan un update."
The price is CA $178
CA $201 total
includes taxes & fees
Jun 17 - Jun 18
Hibiscus Suites - Gateway to Siesta Key
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.

Southwest Florida Vacation Homes information

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