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Southwest Vacation Rentals

(3085 rentals)
Anna Maria Island House
Sleeps 17, 7 bedrooms, 7.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Ocean Star! .01 Miles to Amazing Gulf Coast Beaches Private Heated Pool/Spa with Outdoor Seating & BBQ Beach Equipment Available for Use Every Bedroom Has a Private Bathroom Fully stocked kitchen for all of your favorite home-cooked meals High-speed Wi-Fi, Smart lock for Self Check-in...

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$720
avg per night
Bradenton House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Blue Chill! Close proximity to Lakewood Ranch, Sarasota, and Tampa Short Drive to the World Class Beaches of Anna Maria Island Fully stocked kitchen for all of your favorite home cooked meals Modern & Fully Updated! High speed Wi-Fi, Smart lock for Self Check-inThis 3-bedroom...

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$158
avg per night
Venice House
Sleeps 6, 3 bedrooms, 3 bathrooms

Distance to beach: 0.9 miles to Venice Beach

Key Amenities

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

About this property

Modern, beautifully furnished private oasis ideally located steps from downtown shops and restaurants, and minutes from Venice beach. 3 bedroom, 3 bathroom + office. Single-level, split plan comfortably accommodates up to 6 guests. Most pets welcome.The fabulous home offers high, airy ceilings...

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Bradenton House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Boho Bungalow! Close proximity to Lakewood Ranch, Sarasota, Tampa, and Gulf Coast Beaches Private Screened in Heated Pool Community Pickle Ball, Tennis Courts, Basketball Court, Pool, & Playground Pet Friendly, Fenced in Backyard Beach chairs, wagon, and a cooler available Fully...

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$103
avg per night
Englewood Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

10% OFF ANY RENTAL OF 30 DAYS OR MORE January and February must be booked togetherWaterfront Island 2/2 Condo-Perfect for Boaters and Beach LoversATTENTION BOATERS BEACH LOVERS! You will love this Updated Ground Floor 2/2 Condo that sits right on Lemon Bay with access to the beautiful beaches...

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Venice House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your Venice escape! This charming 3-bedroom, 2-bath pool home sits on a spacious corner lot in a quiet neighborhood—just minutes from beaches, nature trails, and local attractions. With stylish updates, private outdoor space, and a screened-in pool, this home offers the perfect blend...

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Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Seasonal rental of luxury Condo in the heart of Naples. 3B,2B, new furniture, pool and clubhouse. Close to beaches, shopping, dining and Artis Naples. 5,000.-$per month all in, only January and February available at this time, please call , or email : eco44333@

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Lehigh Acres House
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 23 miles to fort myer vanderbilt

Key Amenities

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

About this property

Welcome to Magic Paradise Pool Home! Escape to a serene retreat in SWFL Florida. This fully furnished 3-bedroom, 2-bath home offers a private pool (heated for an additional cost), scenic lake views, and a spacious garden. Perfect for families or groups, it accommodates up to 8 guests. Pet-friendly (pet...

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Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

It’s all about location on vacation, and Reef Romance does not disappoint! Sail away to this beautiful four-bedroom, four-and-a-half-bathroom custom-built home for a dose of luxury at the beach. Located on the prestigious north end of Anna Maria Island, you’re just a few houses away from the...

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Anna Maria Island Villa
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Sea Site Unit A! 100 Steps to the World Class Beaches of Anna Maria Island Close to Restaurants, Shopping, and More Water Views from Balcony King, King, & Two Full Beds High speed Wi-Fi & Smart lock for Self-Check-inWaking up to a view of the coast with your morning cup of...

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$250
avg per night
Fort Myers Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • WiFi

About this property

Home, 2 Bedrooms, 2.0 Baths, (Sleeps 4) STR #22-0469Fort Myers Beach is coming back, and the beach is open to enjoy fun in the sun! This home has been fully restored and is now accepting reservations!While our Fort Myers Beach community continues to rebuild from the impact of Hurricane Ian and...

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Featured review

"Wonderful Vacation Home"

We stayed at 120 Del Mar on March 1-9. The house was cute and only a 3 minute walk to the beach. The beach cart, chairs, towels were so convenient. We enjoyed the bikes also. The kitchen had everything...

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Fort Myers House
Sleeps 1, 1 bedroom, 1 bathroom

 

Anna Maria Island House
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Have you been dreaming about the water here on Floridas Beautiful Gulf Coast? Well, come enjoy "Bay Dreamin" Walk To Bayfront Park located directly across the street! .03 Miles to Pine Ave. Fishing, Shopping, Restaurants, and more! Private Heated Pool/Spa, Putt-Putt Golf Fully Renovated...

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$595
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 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! Beach chairs, wagon, and a cooler available Fast WIF, Smart TVs, &...

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$103
avg per night
Anna Maria Island Townhome
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

VRC 304 60th St Unit A Holmes Beach FL 34217Escape to Azure Beach House—a stunning 3-bedroom, 2-bathroom vacation home nestled in the heart of Holmes Beach on Anna Maria Island. Located just minutes from the pristine Gulf beaches, this beautifully designed home offers the ideal setting for...

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Punta Gorda Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Beautiful walk up second floor condo with stunning sunrise lanai as well a STUNNING second Lanai to watch the spectacular sunset. Fully appointed condo with king Master and queen second bedroom and also a den with a sofa bed. Brand new golf community with all the amenities including resort style pool,...

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New
Bradenton House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Garry's Landing! Short Drive to the World Class Beaches of Anna Maria Island Enjoy Fishing off Dock! Kayaks Available Bring your Boat or other Water Toys! Beach chairs, umbrella, wagon, and a cooler available Fully stocked kitchen with Air Fryer, Keurig, and BBQ Grill High-speed...

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$103
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Be one of the very first to stay in this LUXE, newly constructed custom home. Heated pool & spa, rooftop deck with GULF VIEWS. Grill, custome kitchen, wet bar on thrid level. ALL THE BELLS AND WHISTLES! This stunning 4 bedroom + bonus room (2 additional twin beds), 5 bathroom home only 2-minute...

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Featured review

"Holmes beach"

This is an amazing property! Location and pool and lanai were awesome! Private and close to everything! There was a Publix right up the road also. We rented golf carts from zoom around and we could easily...

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$438
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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$185
avg per night
Anna Maria Island House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

VRC Book with confidence: NO CANCELATION FEES Cancellation Policy (Effective for reservations made on or after August 13, 2025) $500 deposit due at time of booking; balance due 60 days prior to arrival Cancel 60+ days before arrival → Full refund (no fees). Cancel within 60 days of arrival →...

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$153
avg per night
Fort Myers Beach Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Come make our NEWLY REMODELED condo your vacation getaway on beautiful Fort Myers Beach.Features of the complete newly remodeled condo... - All new tile floors throughout - Fully remodeled bathrooms - Completely remodeled kitchen to include white cabinets, stainless steel appliances & beautiful...

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Featured review

"First trip to Fort Myers Beach"

This condo is amazing! The unit is beautifully decorated and very welcoming. The kitchen is well equipped. Because of Covid we ate in a lot and appreciated having everything we needed. There is still...

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Anna Maria Island Villa
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Sea Site Unit B! 100 Steps to the World Class Beaches of Anna Maria Island Close to Restaurants, Shopping, and More Private Patio for Beach Equipment and Grilling King, King, & Two Full Beds High speed Wi-Fi & Smart lock for Self-Check-inWelcome, too Sea Site Retreat Unit B!...

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$250
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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$195
avg per night
Bonita Springs Apartment
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Beautiful gulf-facing apartment across the street from the beach; 2 bedrooms in a well-maintained building with pool, manicured grounds and large lanai from which to enjoy the gulf breeze.

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

Distance to beach: 12 miles to Fort Myers Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

This is a 2 bedroom and 2 bathroom (full) condo. We are on the ground level with your own covered parking space. You have a beautiful lanai to enjoy your morning coffee or a glass of wine in the evening. This is a quite peaceful area. There is a swimming pool, jacuzzi and a BBQ pit for your pleasure.

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New
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Escape to paradise at Endless Summer . A perfect retreat in the heart of Naples Florida . The unit is a first floor accessible condo in the vibrant Falling Waters community . This beautiful gated community offers resort style heated saltwater pool . The pool is one of the largest in the area with water...

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New
Nokomis House
Sleeps 3, 1 bedroom, 1 bathroom

About this property

Our property is close to the beach and walking distance to 5 restaurants. We are less than two miles from the comas.Beach! We have you covered on beach equipment.We supply wagons, chairs, towels and umbrella. The legacy trail is only across the street.Through the park. We offer a relaxing backyard equipped...

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$171
avg per night
New
Marco Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

From your private balcony, watch the sun melt into the horizon each night.This top-floor 3-bed/2-bath condo is perfect for family and friend groups — close enough to enjoy the beach, pool, spa, and onsite restaurant, yet just moments away from all the island offers: paddleboarding, shelling,...

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New
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

About this property

Come experience luxury in a 2 bedroom, 2 bath in one of our beautiful Naples Florida rentals. The Naples Continental Club is one of the finest beachfront rentals. The space: King size beds, walk in shower, fully furnished. Open concept kitchen ,an island with plenty of seating, and new quality appliances...

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New
Marco Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Casa DeMarco is a small, 27 unit building located on a quiet street with only a 10 minute walk to the South Beach Access. DESCRIPTION: 2 Bedroom/2 Bathroom Large screened in Lanai: 8’4” x 27’4” New appliances in Kitchen: Bosch Dishwasher, Fisher & Paykel Refrigerator,...

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New
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Completely remodeled unit in a quaint, lush courtyard-style community. This condo is furnished and decorated as if it was your 2nd home. French Oak floors throughout the living and bedroom areas, walk in showers with high end finishes, instant water heater for never ending hot showers, fully furnished...

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Punta Gorda House
Sleeps 7, 3 bedrooms, 2 bathrooms
7 reviews

Distance to beach: 4 miles to port charlotte

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

HE HOUSE 2800 sq. foot 2 car garage When you enter the house you will appreciate the sophisticated modern decor and attention to detail, making you feel right at home. The living room, dining room and kitchen have an open floor plan and fully updated. The kitchen has granite counter tops and stainless...

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Featured review

"Amazing Holiday Villa"

Brian and Denise were the perfect hosts, they meet us on arrival and gave us a wee tour of the house showing us how the equipment worked and familiarised us with the villa. This is a spacious well equipped...

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Naples House
Sleeps 8, 4 bedrooms, 3 bathrooms

Distance to beach: 1 miles to Naples Pier, Miramar beach,

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Waterfront Home overlooking SPECTACULAR bay views in Royal Harbor, near Fifth Avenue South.The enchanting Naples waterfront lifestyle can be fully experienced in this upscale residence. This home is located on Naples Bay, it features 3 bedrooms with plenty of space for the entire family. Large...

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Fort Myers Beach Condo
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Escape to Sunny Paradise: Luxurious Penthouse Condo at Fort Myers Beach!Are you ready to trade snowflakes for sunrays? Welcome to your dream winter escape on Fort Myers Beach! This stunning, newly remodeled penthouse condo is your ticket to a luxurious and warm winter.Why You'll Love It:Spacious...

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Cape Coral Villa
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Villa Long Island (southern exposure) was built in 2020 in the desirable Southwest of Cape Coral in a quiet neighborhood with boat access to the Gulf of Mexico. The open floor plan of 2,234 sqft with high ceilings offers a spacious living area with open kitchen and kitchen counter, dining area for 6 people,...

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Featured review

"Villa LongIsland"

We thoroughly enjoyed our stay at the Villa Long Island. It is really a very first class home. Everything was in good working order and we had no issues with the house whatsoever.

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