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Southwest Vacation Rentals

(3391 rentals)
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...

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$166
avg per night
Cape Coral House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Vacation days are too precious to spend anywhere ordinary.Here, mornings begin with coffee overlooking the water as the neighborhood slowly comes to life. By afternoon, the pool has become headquarters for the family while lunch sizzles on the outdoor grill and everyone drifts effortlessly between...

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Bradenton House
Sleeps 12, 3 bedrooms, 3.5 bathrooms

Key Amenities

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

About this property

Lake O' Woods by Anchor Down Vacation Rentals Wake up to still water and glowing pool lights on a private, gated acre where the fun never stops — a 4-hole putting green, full arcade, and pool table keep everyone entertained between beach trips. This Bradenton lakefront vacation rental sleeps...

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$244
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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$979
avg per night
Bradenton House
Sleeps 12, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Tropical Tranquility! Close proximity to Lakewood Ranch, Sarasota, and Tampa Short drive to beaches Fully stocked kitchen for all of your favorite home cooked meals High speed Wi-Fi included Smart lock for Self Check-inThis beautiful, newly renovated, and furnished 4 bedroom...

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$225
avg per night

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Bonita Springs House
Sleeps 9, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

NEW! AVAILABLE 2025 SEASON! Welcome to our beautiful 3-bedroom, 2-bathroom vacation destination near Bonita Beach, where every day feels like an endless summer. Escape to paradise in this stunning and exquisitely decorated 3-bedroom, 2-full bath heated pool home just a 5-minute drive to nearby Bonita...

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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 Driftwood Dreams Just Minutes to Anna Maria Island & Bradenton Beach Private Resort-Style Pool & Fully Fenced Backyard Fishing poles & Shark Tooth Hunting gear Beach Chairs, Wagon, Cooler, Toys, & More! Game Room w/ Arcade Games, Bumper Pool, Foosball & Poker...

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$203
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! 4 Beach chairs, wagon, and a cooler available Fast WIF, Smart...

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$181
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 Cortez Cabana! Short drive to the World Class Beaches of Anna Maria Island Close proximity to Lakewood Ranch, Sarasota, and Tampa Private Heated Pool, Outdoor Seating with TV, BBQ Grill Private Boat Dock, Short Drive to Gulf High-speed Wi-Fi, Smart lock for Self Check-in, Luxurious...

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$525
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Bay Dreamin By Anchor Down Vacation Rentals Wake up to open water and views of the Sunshine Skyway Bridge from your own private deck at the tip of Anna Maria Island. This fully renovated retreat pairs a heated pool and spa with a backyard putting green, so lazy mornings and playful afternoons both have...

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$582
avg per night
Bradenton House
Sleeps 10, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Welcome to Twin Palms Oasis! Short drive to the World Class Beaches of Anna Maria Island Screened in Heated Private Pool & Spa Pool Table, Arcade Basketball, Pac-Man, Poker & More Beach Chairs, Wagon, Cooler & More Family friendly with pack'n'play Fully stocked kitchen...

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$237
avg per night
Bradenton House
Sleeps 10, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Welcome to Sandys Coral Retreat! Short drive to the World Class Beaches of Anna Maria Island Bring your Boat or other Water Toys! Fish off the Dock! Screened in Heated Pool, Hot Tub, Outdoor Seating with TV, BBQ Grill Canal Front with Quick Access to SRQ Bay Pet Friendly, Fenced in Yard! High-speed...

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$254
avg per night
Bradenton House
Sleeps 9, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Nautical Escape! Short drive to the World Class Beaches of Anna Maria Island Bring your Boat or Other Water Toys, Private Dock off Warner East Bayou Private Heated Pool, Fire Pit, Arcade Games and More Beach chairs, wagon, and a cooler available Fully stocked kitchen & BBQ for...

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$220
avg per night
Bradenton House
Sleeps 8, 3 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Welcome to Anna Maria Seascape in Hunters Point! 1 Mile to the World Class Beaches of Anna Maria Island Bring your Boat! Personal Boat Slip, Park Trailer in Garage Outdoor Seating with TV, BBQ Grill, Fire Pit, & Amazing Views Private Heated Pool, Backyard Oasis, Biggest Deck in the Community...

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$272
avg per night
Bradenton House
Sleeps 14, 5 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Montauks Point Hosted by Anchor Down VR Sink into the heated pool while the kids chase golf balls across the putting green, then trade the arcade for the fire pit as the sky turns pink. There is room for every generation in this fenced backyard, and Anna Maria Island is a short ride away. Montauks Point...

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$289
avg per night
Bradenton House
Sleeps 8, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Coco Loco! Short drive to the World Class Beaches of Anna Maria Island Close proximity to Lakewood Ranch, Sarasota, and Tampa Private Heated Pool, Outdoor Seating, BBQ Grill Private Boat Dock, Short Drive to Gulf High-speed Wi-Fi, Smart lock for Self Check-in, Luxurious Linens and...

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$244
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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$187
avg per night
Bradenton House
Sleeps 10, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Mermaid Villa! Short drive to the World Class Beaches of Anna Maria Island Private Boat Dock, Bring your Boat! Enjoy Kayaking, Bike Riding and so much more Close proximity to Lakewood Ranch, Sarasota, and Tampa Private Screened in Heated Pool, Outdoor Seating, BBQ Grill High-speed...

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Featured review

"Dolphins at your feet most mornings and lots to do."

Dolphins playing off the deck in the canal most mornings, one time for 20 minutes. Fishing not bad from the Kayaks. The beach's are only a five minute drive or bike there in ten. Stay home and swim in the...

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$221
avg per night
Bradenton House
Sleeps 8, 4 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Turtle Bay Cottage Close proximity to Lakewood Ranch, Sarasota, Tampa, and Gulf Coast Beaches Private, Screened-in Heated Pool Water views and Pond Fishing Community Pickle Ball, Tennis Courts, Basketball Court, Pool, & Playground Beach chairs, wagon, and a cooler available ...

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Featured review

"Fantastic vacation!!!!’"

Swfl rentals is an amazing company to rent a vacation home through!! They make sure everything is as advertised. We had an amazing vacation thanks to them!! Will happily use them for our next Florida...

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$218
avg per night
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...

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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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$154
avg per night
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...

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$266
avg per night
Bradenton House
Sleeps 11, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Aqua Luxe Escape located just off the Palma Sola Bay in Bradenton, Florida! Heated Pool & Spa Combo with Sun Shelf, Waterfall, & Bubblers Outdoor Kitchen, Covered Lounge Area & Smart TV Beach Chairs, Wagon, Cooler, & Umbrella 5 Bedrooms | 4 Bathrooms (3 Ensuite + Jack...

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$622
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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$193
avg per night
Bradenton House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Sunshine Cove located in Bradenton, FL Less than 4 miles to Bradenton Beach & the world-famous beaches of Anna Maria Island Private HEATED pool, firepit, BBQ grill, fenced turf yard & pet-friendly Beach chairs, wagon, and a cooler available Family friendly with pack'n'play...

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$187
avg per night
Bradenton House
Sleeps 7, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Coastal Vibes! Short drive to the World Class Beaches of AMI! Fully stocked kitchen for all of your favorite home-cooked meals Amazing Outdoor Entertainment area! High-speed Wi-Fi, Smart lock for Self Check-in*Only 1 boat or trailer allowed at the home at a time. Work trailers...

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$185
avg per night
Palmetto House
Sleeps 8, 4 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Villa Villekulla! 1 Mile from Bradenton Convention Center & Downtown Bradenton .5 Miles to Palmetto City Fishing Pier & Riverhouse Restaurant Short drive to the World Class Beaches of Anna Maria Island Private Screened in Heated Pool Fully stocked kitchen for all of your...

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$191
avg per night
Bradenton House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Dolphin Cabin! Screened in Private Pool, Sunset Views, Dolphin Activity Short Drive to the World Class Beaches of Anna Maria Island Bring your Boat or other Water Toys! Fully stocked kitchen with BBQ Grill High-speed Wi-Fi, Smart lock for Self-Check-inWelcome to Dolphin Cabin!...

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$244
avg per night
Bonita Springs House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Great Location! Just Steps to Beach! Bonita Bliss is conveniently located directly across the street from the beach and only 200 steps to Public Beach Access #8. The open-concept living and kitchen area is perfect for family gatherings and entertaining guests. Kitchen is well appointed with granite countertops,...

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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...

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$266
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

24th St Beach House by Anchor Down Vacation RentalsTucked between the Gulf and the Bay in Bradenton Beach, 24th St Beach House puts both coastlines within a short stroll, plus a neighboring park with a kayak launch, tennis, and a playground. Recent updates keep things feeling fresh, and a full kit...

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$206
avg per night
New
Estero Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Apartment contains two plush bedrooms with king and queen size beds plus a den/office with pull out sleeper sofa. Living room is cozy & spacious with the ability to seat up to 10 people comfortably Kitchen features, cozy breakfast nook, counter seating as well as a coffee maker, microwave, and...

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$149
avg per night
New
Naples Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Discover the perfect blend of comfort, style, and the Florida lifestyle in this newly renovated 2-bedroom, 2-bathroom condo with a spacious den and private garage in the desirable Calusa Bay community.Thoughtfully updated and ready to enjoy, this inviting retreat offers the perfect home base for your...

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$165
avg per night
New
Venice Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 10 miles to Manasota

Key Amenities

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

About this property

Blue Heron Luxury Condo17630 Opal Drive #308 | Venice, FL 34293Available November 1, 2027 | 30-Day Minimum StayEscape to paradise at Blue Heron Luxury Condo, a beautifully furnished, turnkey three-bedroom, two-bathroom retreat in the desirable Wellen Park Golf & Country Club community...

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$181
avg per night
New
Cape Coral House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Canal-Front, Family & Dog-Friendly Home with Private Saltwater Pool, Dock, WiFi, & Covered LanaiExperience peaceful views of the canal and enjoy many nature sightings from your private dock or while sitting on your own covered lanai. Sip a beverage and make dinner on the gas grill or cook...

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New
Sarasota House
Sleeps 10, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

This Tropical Island Oasis Escape boasts a private pool and ample room inside and outside for family and friends. Conveniently located on Siesta Key with walkability to the quaint Shell beach with ocean access or take a short bike ride or drive to the beautiful beaches of Siesta Key or dining and shopping...

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$675
avg per night
New
Sarasota Mobile home
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Located in Orange Acres Estates at Clark Rd and I 75 *** Pet free community ***Cozy home in a clean family run community. 765 sq ft with additional living space in attached screened in lanai.Carport and shed with washer/dryerBeautiful, deep pool with newer outdoor furniture and umbrellas....

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$47
avg per night
New
Englewood Studio
Sleeps 3, 0 bedrooms, 1 bathroom

About this property

YEllow Gecko is part of Gecko House on Manasota Key. It has a comfortable king Nectar mattress which couples enjoy, and a Murphy XL cabinet bed to accommodate the extra friend or child. It is self-contained with a galley kitchen, including Keurig and regular coffee maker, plates, silverware, microwave,...

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Siesta Key Villa
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 100 yards to Siesta Key private area of beach

Key Amenities

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

About this property

This updated Villa is on the beach side of Siesta Key, with private beach!!! It does not get better than this!! Fully renovated private villa on beachside. In 1 to 2 mins you can have your feet in the sand. Parking directly in front of villa.There is an amazing huge heated pool,, one of the biggest...

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Featured review

"Fantastic vacation, great rental!!"

Highly recommend!! Property was very clean, interior is updated; we had a very comfortable stay. Fully stocked with towels and essential kitchen cookware. Ruth was great to work with, very responsive and...

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Fort Myers Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Lovely first floor condo in beautiful Heritage Palms. 2 BR 2 BA. Freshly painted and decorated with TV in living room and both bedrooms. Cable and internet included. There are 2-18 hole golf courses, tennis and pickleball courts, 9 swimming pools, practice range, activity center, fitness center....

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Featured review

"Heritage Palms"

Friendly people as well as staff and professionals. Great golf courses and club house as well as fitness center and practice facilities. Would highly recommend!

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Babcock Ranch House
Sleeps 7, 3 bedrooms, 3 bathrooms

Distance to beach: 40 miles to Multiple Options

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Stunning 3-Bedroom Calusa-Style Home with Pool in Webb’s Reserve – Luxury Meets Florida SunshineDiscover your ultimate seasonal retreat in this beautifully designed 3-bedroom, 3-bath Calusa-style home in the exclusive Webb’s Reserve community at Babcock Ranch. Blending coastal contemporary...

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Manasota Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Welcome to your dream beachfront escape in beautiful Manasota Key, Florida! This stunning 2-bedroom, 2-bathroom condo offers a perfect blend of luxury, comfort, and breathtaking views of the Gulf of Mexico.- Prime Location: Situated directly on the Gulf of Mexico, you'll enjoy unparalleled access...

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Featured review

"Very nice"

We loved our stay at this condo. On the beach and close to stump pass. Condo was spacious and clean. Kitchen was well equipped.

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