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Southwest Vacation Rentals

(3270 rentals)
Bradenton Condo
Sleeps 5, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Manatee Cove #106! 2.4 miles to the World Class Beaches of Anna Maria Island Personal slip available for a 20ft boat, No Trailer Parking Available Beach Wagon, 4 Chairs, Cooler, & More available for use Close proximity to Restaurants and Bars Community Dock, Waterfront Seating,...

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$118
avg per night
Bradenton House
Sleeps 10, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Mermaid Bay Located in San Remo Shores just off Anna Maria Island! Short drive to the World Class Beaches of Anna Maria Island Private Dock, Bring your Boat or other Water Toys! Enjoy Kayaking, Bike Riding and so much more Private Screened in Heated Pool, Outdoor Seating, BBQ Gas...

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$221
avg per night
Bradenton House
Sleeps 14, 5 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Montauks Point! Short Drive to the World Class Beaches of Anna Maria Island Close proximity to Lakewood Ranch, Sarasota, and Tampa Pet Friendly, Fenced in Backyard Large Exterior Lanai With Smart TV Fully stocked kitchen for all of your favorite home cooked meals High speed Wi-Fi,...

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$469
avg per night
Bradenton Townhome
Sleeps 6, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Welcome to Cappy Hour! Where every day on vacation is happy hour at Cappy Hour! Close proximity to Lakewood Ranch, Sarasota, and Tampa Short drive to World Class Beaches of Anna Maria Island Community Pool, Pickleball/Tennis Courts, Playground and Basketball Hoop Fully stocked kitchen for all...

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$102
avg per night
Bradenton House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Bloom Lagoon! Short Drive to the World Class Beaches of AMI Basketball Hoop, Bikes, & Beach Equipment Available for use! Close proximity to Lakewood Ranch, Sarasota, and Tampa Private Screened in Pool Area Fully stocked kitchen for all of your favorite home-cooked meals High-speed...

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$184
avg per night

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Bradenton House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Blue Heron House! Close proximity to Lakewood Ranch, Sarasota, Tampa, and Gulf Coast Beaches Private Heated Pool, Backyard Oasis Community Pickle Ball, Tennis Courts, Basketball Court, Pool, & Playground Beach chairs, wagon, and a cooler available Fully stocked kitchen & BBQ...

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Featured review

"Fantastic Vacation"

This home is so darn cute and contains everything you need/want for a great vacation. The decor is outstanding, the bedrooms comfortably large and the location is close to stores and restaurants. The location...

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$174
avg per night
Bradenton House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Cape Vista Getaway! Short Drive to the World-Class Beaches of Anna Maria Island Close Proximity to Lakewood Ranch, Sarasota, and Tampa Private Heated Pool, Putting Green, Loungers, & More Fully Stocked Kitchen for All of Your Favorite Home-Cooked Meals High-Speed Wi-Fi, Smart...

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Featured review

"Average Home"

The home was nice but needed updating and cleaning. The pool was heated and I got to enjoy it during the evening.

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$192
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to "Down On The Island" the perfect beach destination for your next family getaway! .01 Miles to the World Class Beaches of Anna Maria Island Nearby Park with Basketball, Playground, Kayak Launch Fully Stocked Kitchen for Home-Cooked Delights Seamless Arrival with Fast Wi-Fi...

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$245
avg per night
Bradenton House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Cortez Chic! Short drive to the World Class Beaches of Anna Maria Island Close proximity to Lakewood Ranch, Sarasota, and Tampa Screened In, Heated Private Pool with water View Cinema Room and Coffe Bar Golf Courses Nearby High-speed Wi-Fi included, Smart lock for Self Check-in...

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$219
avg per night
Bradenton House
Sleeps 10, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Agave Sun! Short drive to the World Class Beaches of Anna Maria Island ​​​​​​​ Screened in Heated Pool/ Backyard Oasis Close proximity to IMG Academy, Parks & More Fully stocked kitchen for all of your favorite home-cooked meals High-speed Wi-Fi included, Smart lock...

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$299
avg per night
Bradenton House
Sleeps 19, 5 bedrooms, 5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Retreat at Palma Sola Bay your Waterfront Oasis! 150+ Feet of Direct Palma Sola Bay Waterfront Private Heated Pool & Spa (Pool Heat Included) Private Dock – Fish, Kayak, Paddleboard or Bring Your Boat Separate Guest House + Game Room Sleeps 19 Guests Comfortably Walk...

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Featured review

"Perfect"

We were a group of soccer moms (and one dad) there for a few days for a tournament. This house was everything we could have wanted! Clean, well appointed, excellent location, I can't say enough!Nights...

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$936
avg per night
Englewood House
Sleeps 16, 6 bedrooms, 4.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

About this space Rare 1-acre beachfront estate on Manasota Key. Main house (3BR) + separate guest house (3BR) sleeps 16. Private pool, putting green, ocean-facing sun room, balconies with chairs and beach views on both houses. Guest house with 2 car garage has stairs directly to the beach. Gated entry...

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Featured review

"The beach was beautiful, with clear water, endless shark teeth to find, we saw manatees swim by, sea turtles nesting!"

This home truly had it all. From the moment we arrived, the hosts made us feel less like guests and more like old friends. Their kindness, hospitality, and attention to every detail made our stay so special.The...

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New
Naples House
Sleeps 12, 6 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Stunning, gulf views throughout the property. Gorgeous sunsets every night, just a few steps from your balcony to a large yard that faces the beach. Grand wrap around porches that face the beach and water, with gracious seating areas. Contemporary home with five bedroom suites plus a den that accomodates...

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Bradenton House
Sleeps 10, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Seas The Day! Short drive to the World Class Beaches of Anna Maria Island Private Screened in Heated Pool, Pac Man, Golden Tee, Smart TVs Available for Use Fully stocked kitchen & BBQ for all your cooking needs! 4 Beach chairs, wagon, and a cooler available Fast WIF, Smart...

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$200
avg per night
New
Naples House
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 11 miles to Wiggins Pass Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Experience refined seasonal living in Naples, FL at this beautifully appointed 3-bedroom, 2-bath coach home in the prestigious gated community of LaMorada. Available immediately offered fully furnished turnkey, this elegant residence is move-in ready and designed for effortless comfort and style. Inside,...

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New
Port Charlotte Apartment
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Gorgeous one bedroom, one bath private apartment for rent, fully furnished

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New
Venice Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 9 miles to Venice Beach Sharkey's Pir

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Spectacular veiws of the Plantation golf course fairway and lake from your Lanai, as seen on the LPGA qualifiers. This beautiful, well appointed 2 bedroom, 2 bath condo is located on the 3rd floor with prime location. Quiet retreat yet in close proximity to restaurants, beaches, shopping, Cool Today Park,...

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New
Naples Condo
Sleeps 4, 0 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

A cozy place with landscape viewing on porch ! Close to clubhouse, pool, hot tub, pool room and fitness center. Pickle ball court nearby and tennis court. Just down the road walking distance is a plaza with breakfast dining, nails, multiple businesses.

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Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 6 miles to Many

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Very social building ! Brand new clubhouse opened Spring 2025 featuring 3 dining venues, 2 outdoor bars, and a beach entry pool with food and beverage service available. This 15 million dollar renovation has made Countryside the talk of Naples and the place you want to spend your winter. Super clean...

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Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 11 miles to Delnor-Wiggins Pass State Park

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Heritage Bay Condominium-- Have yourself a five star vacation! Well cared-for, 1st floor, two bedroom 2 bath condo. Golf (all 27 holes) is available at this unit!This young, freshly painted ( 2024 ), two bedroom unit has a fully-equipped kitchen with stainless steel appliances, Corian countertop,...

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Featured review

"Best vacation I’ve ever had."

Spent 4 months at this condo in Naples. The unit is located at heritage bay. The condo is beautifully furnished along with all the amenities included. We had such a wonderful time. We were near all of the...

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