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Southwest Vacation Rentals

(3278 rentals)
New
Naples House
Sleeps 14, 7 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Stunning, spacious living in a home that is classic in style but has a southern flair. An ideal location that is walking distance to the beach, close to Third Street South and Fifth Avenue South for world-class restaurants, shopping, entertainment, art galleries, and more. A distinguished estate with...

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North Fort Myers House
Sleeps 10, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Welcome to this beautifully maintained waterfront home located on a canal in North Fort Myers. This charming 3-bed, 2-bath single-family residence offers 1,278 sq ft of comfortable living space on a spacious 9,409 sq ft lot. Built in 1961 with solid concrete block construction and modern updates, the...

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Fort Myers Villa
Sleeps 6, 3 bedrooms, 3.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Happiness is Rentable: The Lakehouse in South Fort MyersWelcome to The Lakehouse, a beautifully designed, spacious retreat nestled on a serene lake in the charming McGregor Woods community of South Fort Myers—Florida’s renowned “City of Palms.” This architect-designed 3,100...

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Featured review

"Outstanding vacation Rental"

We had a wonderful stay for two months at The Lake House in McGregor Woods—it truly lived up to its description and more. The home is beautifully designed, incredibly spacious, and perfectly set on a...

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$280
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 Grill High-speed...

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Fort Myers Beach Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Some views are beautiful. This one is alive. From the 3rd floor corner balcony of this remodeled Lovers Key Resort luxury condo, the Estero Bay is right there — close enough to watch the morning light move across the water, and close enough to catch the dolphins, manatees, tropical fish, and birds...

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Featured review

"Nice view, nice amenities"

The location being on the south end of estero is quiet and convenient to Bonita beach and Naples. The unit was clean and had all of the necessities. You can walk to lovers key beach but is about a mile....

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Cape Coral House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Come back to Southwest Florida - the area beaches are open for your enjoyment!This waterfront pool/spa home offers guests to our area the classic Southwest Florida lifestyle! Located on a wide fresh-water canal near central Cape Coral, you will enjoy swimming in your own private heated pool, relaxing...

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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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Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Villas by the Sea 4! .01 Miles to the World Class Beaches of Anna Maria Island .02 Miles to Bridge Street Pickleball Courts & Playground Across the Street Beach Wagon, Chairs, Umbrella, & Cooler available for use Heated Community Pool Fully stocked kitchen for all of your...

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Featured review

"Very Nice Condo, close to beach"

Our stay was very nice. Found it odd that Kleenex weren't furnished, as well a basic bathroom supplies, shampoo and body wash. I just assumed they would be there. At the price point of over $400 daily,...

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Longboat Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
5 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This ground floor waterfront condo located in a gated community of Longboat Harbour and is one of Longboat Keys most desirable social communities. This one bedroom, one bathroom, first floor unit has walkout access to Sarasota Bay where you often see dolphins and manatees from your lanai. This unit is...

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Featured review

"Grreat stay atLong Boat Harbour"

What a beautiful development Long Boat Harbour is! My wife and I stayed in unit E104 for 2 months. Haley is a very gracious host to allow us to stay in her home. We had such a wonderful time, we did...

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New
Fort Myers Beach Condo
Sleeps 7, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Resort living-Monthly Rentals only Beautiful beachside condo with views overlooking the pool, soft, sugary beach, sunsets and gulf beach from your private balcony! Recent updates include luxury vinyl plank style flooring and freshly painted throughout! This 3rd floor condo features a split 2 bedroom...

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Anna Maria Island Villa
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Beachcomber showcases spacious decking and a bright, open-concept living, dining, and kitchen area, radiating coastal luxury and charm. The main bedroom features a sumptuous king-size bed and a stylish en-suite bathroom with a soaking tub and a shower, while the second bedroom can be configured as either...

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Anna Maria Island House
Sleeps 7, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Hammock Hideaway! .02 Miles to Pine Ave. Shopping, Restaurants, and more! .03 Miles to AMI Beaches 8 Hole Mini Golf Course Private Heated Pool, Jacuzzi, BBQ Grill, Sun Loungers Beach chairs, wagon, and a cooler available Family friendly with pack'n'play and highchair High-speed...

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Featured review

"How can we live here?"

We absolutely loved our stay in Holmes Beach! The location was perfect — so central and convenient to everything, which made exploring the area incredibly easy. The house itself was beautifully remodeled:...

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Punta Gorda Condo
Sleeps 4, 0 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Escape to an oasis of comfort and luxury with 4th floor Birkdale open-concept condo at Heritage Landing with golf access. This exclusive two-bedroom, two-bathroom unit offers stunning views of a pristine nature preserve and a beautiful lake from the privacy of your own lanai. Entertaining guests is effortless...

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Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Pool
  • WiFi

About this property

Welcome to Villas by the Sea 5! .01 Miles to the World Class Beaches of Anna Maria Island .02 Miles to Bridge Street Pickleball Courts & Playground Across the Street Beach Wagon, Chairs, Umbrella, & Cooler available for use Fully stocked kitchen for all of your favorite home cooked...

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Cortez House
Sleeps 9, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Manatee Dreams! 1 Mile to the World Class Beaches of Anna Maria Island Bring your Boat or other Water Toys! Personal Boat Slip, Park Trailer in Garage Private Heated Pool, BBQ Grill, Amazing Views, Fish off Dock New Eco-Friendly Construction, Tesla Charging Station, with Elevator Access...

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New
Naples House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool

About this property

Beautiful 4BR, 2BA Pool Home – 5 Minutes to Pickleball CourtsSunny, single‑level rental with four spacious bedrooms, two baths, and a sparkling pool. Open living area, chef’s kitchen with stainless appliances, and a primary suite with private bath. Enjoy outdoor entertaining on the widened...

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New
Fort Myers Beach House
Sleeps 10, 5 bedrooms, 4.5 bathrooms

Distance to beach: 0.0 miles to Gulf-front (direct access)

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your dream beachfront escape on Fort Myers Beach. Spanning three stories, this 5-bedroom, 4.5-bath home is designed for large families or groups seeking space, comfort, and unforgettable Gulf views. Step outside and experience true paradise-your private pool and hot tub sit directly on the...

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New
Cape Coral House
Sleeps 7, 3 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Seasonal & Monthly Pool Home Rental in Desirable South Cape Coral Welcome to this beautifully maintained 3-bedroom, 2-bath pool home located in the heart of South Cape Coral, one of the areas most desirable and convenient neighborhoods. This inviting home offers the perfect blend of comfort, location,...

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New
Marco Island Condo
Sleeps 2, 1 bedroom, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

You come to Marco Island for the Beach, right? The Island's amenities and attractions are merely a distraction from your time away from the Beach. Our luxurious Tradewinds Penthouse Paradise, high up in the sky, decorated in a coastal contemporary decor, a constant reminder of your place in paradise,...

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$367
avg per night
New
Fort Myers Condo
Sleeps 7, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Experience your ideal getaway in this stunning 2-bedroom, 2-bath condo with a covered carport and ample guest space, located in the sought-after Terraces of Riverwalk community. This immaculate home is perfectly positioned in a vibrant central location, with all your needs just moments away. Step inside...

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$60
avg per night
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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New
Siesta Key House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Distance to beach: 1 miles to Veterans Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

Tucked beneath the palms in the heart of Siesta Key, this thoughtfully designed 3-bedroom home offers the ease of a boutique stay with the privacy of your own retreat.Located just a short walk or bike ride to both Siesta Key Beach and Siesta Key Village, the home is perfectly positioned for days spent...

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New
Venice Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

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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Fort Myers House
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Oh so “home sweet staycation”home! This 2/2 gem in ideallic setting and location awaits you~ Everything you need and more, in this beautifully appointed and incredibly well-furnished home. You’ll thoroughly enjoy relaxing with morning coffee and evening cocktails on this screened lanai,...

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Featured review

"very safe and friendly property. everything is needed was close by. also met realtor and owner as well as her brother in"

the pool was very nice and clean. safe place to stay. trailers and/,or prefab houses are very close to each other. you have to be very quiet. friendly people throughout the park. no activities going on...

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Estero Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Business Traveler Ready With a laptop-ready workspace, a hairdryer, and an iron. An Amazing location west of 41, newly decorated with 1sr floor access. 15 minutes north of Naples and 10 minutes from the Beach, where the best sunsets occur! The space Stunning 1st floor, professionally decorated 2 bedroom...

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Featured review

"N"

Trying to make a reservation for March 2027 -April 2027 can’t let me I live in Glendale hts Illinois not far from you

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Punta Gorda Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 45 miles to Venice Beach

Key Amenities

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

About this property

Imagine starting your day with a freshly brewed cup of coffee and a light breakfast on the lanai, overlooking the serene 11th green and a wildlife refuge area. With our newly installed “no-see-ums” bug screens, you can enjoy the view without any interruptions.After breakfast, take a quick...

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Fort Myers Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

NOW BEING OFFERED FOR SALE BY OWNER! $319,900 -Will. consider long term seasonal renters. COMPARE TO OTHERS in area communities! OPEN HOUSES STARTING APRIL 9 from 11-2 pm daily thru the weekend. SEE IN PERSON! Great references upon request…. This home is even better in person ... take a look first-hand! HURRICANE-BUILT,...

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Naples Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Want to play golf? Head to the beach and enjoy the sun? Well Vasari is where you need to be. A beautiful renovated, turn key, 2300 sq. ft. Coach Home with 3 bedrooms (1 King Bed, 1 Queen Bed and 2 Twin Beds) plus a den with a pull out queen size couch, 2 bathrooms and a single car garage in the highly...

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