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Southwest Vacation Rentals

(3120 rentals)
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

**Welcome to our beachfront Longboat Key condo!If you’re looking for a special two-bedroom, two-bathroom retreat with beautiful waterfront gulf and sunset views, white sandy beach, palm trees and resort style community pool, this may be the place for you! We invite you to look at our photos...

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$493
avg per night
Special Offer
Naples House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 1 miles to Vanderbilt Beach & Delnor Wiggins Park & Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Canal Views from living, kitchen, dining & 1 bedroom! A luxury coastal getaway that just came on the market with an open calendar! Step into paradise and enjoy the amazing outdoors with heated pool, large patio space and spacious Gazebo for evening entertaining! Beautifully appointed with designer...

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$705
avg per night
Marco Island House
Sleeps 7, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Beautiful waterfront pool home. Located right on the water in a wonderfully quiet area of Marco Island, this beautiful home has it all. It is a short walk to restaurants, bars, super market, shops, marina, and yacht club. Also a quick drive to the fantastic Marco Beaches, golf, tennis, the everglades,...

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Featured review

"Great stay"

Great stay. Close to everything. Plenty of room and we'll stocked kitchen with everything you need.

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$326
avg per night
Naples House
Sleeps 10, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Bring the whole family to this great place with lots of room for fun. This stylish home has room for everyone! 4 Large Bedrooms, spacious dining, games, and incredible outdoor living are a few highlights of this tropical oasis. Relax by the pool, man the barbeque, hop on the bikes for a quick ride, keep...

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$594
avg per night
Naples Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 3 miles to VANDERBUILT BEACH

Key Amenities

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

About this property

This meticulously maintained first-floor condo is situated on the 16th hole of a pristine golf course, offering picturesque views of both the serene lake and lush fairways. The property features two well-appointed bedrooms, two bathrooms, and a spacious den, providing ample living space. A large lanai...

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$150
avg per night

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Bonita Springs Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Fantastic condo in highly sought after location of Lighthouse Bay in the Brooks. Second floor unit is bright and cheery with many windows and a Western view overlooking the pond, fountain and beautiful sunsets from the screened lanai. Amenities include 3 community pools, spa, fitness center, tennis, bocce,...

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$179
avg per night
Special Offer
Fort Myers Condo
Sleeps 4, 2 bedrooms, 1 bathroom
4 reviews

Key Amenities

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

About this property

Welcome to Fort Myers! The condo is conveniently located near shopping and restaurants footsteps away and a short drive to the beaches and river views, and downtown. This updated condo has an open concept with luxurious granite countertops and appliances. The kitchen is fully stocked with all that...

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Featured review

"Cute little place"

We actually stayed here for your months: December 2024 thru March 2025. Nice clean 2 bedroom apartment. King bed in master -very comfortable! Kitchen well equipped. large bathroom. Nice bed linens and...

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$135
avg per night
Naples House
Sleeps 8, 4 bedrooms, 6 bathrooms

Key Amenities

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

About this property

Experience the pinnacle of Naples living in this stunning 4-bedroom, 6-bathroom waterfront estate in prestigious Aqualane Shores. With a private office, elegant Mediterranean architecture, and unmatched access to the Gulf, this home blends timeless style with a world-class location.Waterfront Living...

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$1,418
avg per night
Ave Maria Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 27 miles to Wiggins Pass

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

You will not believe the incredible views from this GORGEOUS property. They are jaw-droppingly gorgeous. Beautifully decorated interior designed for your vacation comfort. Stunning Bromelia model features 2 bedrooms + den, 2 bathrooms and Front/back spacious lanais w/ 1car garage! All appliances incl....

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Naples House
Sleeps 4, 3 bedrooms, 2.5 bathrooms
3 reviews

Distance to beach: 5 miles to Naples Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Enjoy your vacation in this beautiful villa with a stunning lakeview. This Villa has 3 bedrooms, two bathrooms and a guest bathroom with toilet and sink. From the master bedroom, the living room and the kitchen you have a beautiful views of the lake and pool.The open kitchen is fully equipped and...

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Featured review

"Home with a view"

We (two couples) stayed in this comfortable house in May/June 2024 and were very happy with it. It provided everything that we needed, especially the kitchen was very well equipped. The house offers a nice...

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$334
avg per night
New
Fort Myers Beach Condo
Sleeps 4, 0 bedrooms, 1 bathroom

Key Amenities

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

About this property

Our 10th floor, gulf-front condominium (Building C) – with spectacular water views from every window - is situated on a white sand beach on the Gulf of Mexico. The waves are gentle, and the gulf-floor slopes gently to an offshore sand bar which provides seven miles of protected beaches. Because...

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$277
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 2 miles to Closest to Delnor Wiggins, Vanderbilt and Bonita

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This beautifully decorated newly remodeled first floor unit has a glass/screen enclosed lanai with a scenic views overlooking the natural preserve. Just steps away from our condo are the tennis/pickleball court and pool areas. This charming condo is conveniently located West of 41 in North Naples, just...

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Featured review

"Super clean and cute place"

Host was great to work with. She was exceptionally accommodating and her unit was exactly as described. Excellent location near tennis, pickleball, and 1 of the 2 community pools. We met many of the regular...

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$174
avg per night
Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
25 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • WiFi

About this property

Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation!Sailfish Gulf Suites is comprised of 4 separate suites. Suite 4 has garden views and is just a few steps to the beach.It features 1 bedroom with king size...

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$346
avg per night
Cape Coral Villa
Sleeps 12, 4 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Escape to your very own slice of paradise at Villa Tranquility Bay, where luxury seamlessly blends with coastal charm in this exquisite Gulf-access villa! Featuring 4 beautifully appointed bedrooms and 3 bathrooms, alongside a heated saltwater pool and spa, custom outdoor grill, deluxe pool table, grand...

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$459
avg per night
Naples House
Sleeps 4, 2 bedrooms, 2 bathrooms
10 reviews

Key Amenities

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

About this property

No hurricane damage !!! Hurricane Protection - The location is perfect, 4 minutes from the privat-beach access and own access to the wonderful and idyllic lake, ideal sun and Ligth. Close to Best Shoping and Dinning, such as Venetian Village and the Waterside Shops - Philharmonic and MuseumOn the...

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Featured review

"Beautiful Home - Well maintained, Excellent handover & Great Location"

We had a fantastic stay! The location is ideal — nestled in a quiet, peaceful neighborhood yet close enough to walk to local shops and restaurants if you're feeling adventurous. One of the standout perks...

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$550
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

A Great Home Away from Home Boatyard Gated Community Comfy Lanai for relaxing and entertaining Bamboo Wood Floors 2 bedrooms (one king and one queen bed) and 2 bathrooms Heated Pool Upgraded features include new paint and wonderful main bedroom walk in shower Wonderful fishing with several...

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$301
avg per night
Ave Maria Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This 2-bedroom, 2-bath Birkdale condo offers an unbeatable location with breathtaking views of the Gordon Lewis Golf Course, serene lake, and nature preserve. And the best part? All you pay is a $30 golf cart fee for access to privileged tee times—no green fees!Situated on the peaceful “quiet...

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Cape Coral House
Sleeps 8, 3 bedrooms, 2 bathrooms
16 reviews

Key Amenities

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

About this property

LOCATION, LOCATION, LOCATION! Welcome to Casa Royal Palms, your perfect home away from home!From the moment you step inside, you’ll feel right at ease in this beautifully updated vacation retreat. Designed for comfort and relaxation, our open-concept home features a brand-new rubber pool deck...

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Featured review

"Great Stay!"

Loved everything about this house. Jaime was always so quick to respond to my questions. There's a new grocery service that delivered groceries the day prior to our stay and it was phenomenal. Loved the...

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Marco Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Come relax in our stunning 11th-floor remodeled beachfront condo, overlooking the sparkling Gulf of America, serene Tigertail Beach, and a peaceful 31-acre nature preserve. Located in the highly sought-after South Seas community on Marco Island, our home offers breathtaking views of the island’s...

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Featured review

"Very comfortable, peaceful and well-equipped condo."

We enjoyed our stay and appreciated the balcony and view. The beds were comfortable and the bedrooms were spacious. Loved the sliding doors from each room to balcony.

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$332
avg per night
Sarasota Condo
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Immerse yourself in beachfront bliss at Lido Bliss: Imagine stepping off the elevator into your private sanctuary. Breathtaking panoramic views of the Gulf of Mexico greet you from your expansive balcony, setting the scene for an unforgettable stay. This meticulously kept, 4-bedroom 3.5 bath haven exudes...

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$1,403
avg per night
Bonita Springs House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

For DIRECT BOOKINGS, Click to HOST and Visit Website !!!!!3 Bedrooms, 3 Baths, Sleeps 6, Maximum 8 With Sofa Bed On Your Mark, Get Set, Go... to Beach Soon! "Beach Love" is in the final stage of being remodeled after surviving Hurricane Ian, and it is "Love...lier" than it was!...

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$1,192
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat DocksLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLRe-opening of 2nd and 3rd floor units on 9/28/25. Property restoration from Hurricane Helene has been mostly completed but there may be some ongoing construction...

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$367
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FLCrescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront...

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$388
avg per night
Cape Coral Villa
Sleeps 5, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Look no further! Your Luxurious Paradise awaits you!Welcome to Blissful Bay, the entry to Paradise! You are sure to find a luxurious and modern coastal Gulf Access Resort-Style pool home at this relaxing vacation getaway. This desirably located southwest Cape Coral villa is on the Gulf Access Waterfront...

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$700
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Escape the Madness to the serenity of Anna Maria's north end. This single family, two bedroom, 2 bathroom, ground level house is located on the far north end of Anna Maria Island near Bean Point. The property is only 250 feet from the sugar sand beaches where you can walk for hours or sit and...

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Featured review

"Awesome!!!"

My family and I stayed at the cottage. House was perfect. It was nice that beach chairs and towels, etc. were available. We also enjoyed using the backyard and grill. The house is literally across the street...

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$359
avg per night
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

This brand new second floor condo, a West Indies Style Architecture completed in 2024 will impress as it features ceramic tile flooring throughout, beautiful appointed cabinetry and a neutral color palette.The condo consists of 2,010 SF total, one-car garage, a large master bedroom ensuite with an...

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$237
avg per night
New
Last Minute Deal
Fort Myers Beach House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 900 feet to Shell Mound Access

Key Amenities

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

About this property

Discover the New Fort Myers Beach with this cozy 3 bedroom / 2 baths Pool and SPA home situated on the island of Forth Myers Beach half way between Times square and the Publix supermarket. The caged Pool and SPA overlook a canal where often fish can be seen jumping out of the water. It has 2 car garage,...

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$322
avg per night
Cape Coral Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

CAPACITY: Up to 6 guests | 3 bedrooms | 2 bathrooms LOCATION: 222 SE 1st Ter Cape Coral, FL, 33990, US BUILT IN: 2024 MAIN FEATURES: Pool (electronically heated) Water/canal view Very close to entertainment (bars, restaurants, Sun Splash Waterpark) Fully stocked beach equipment...

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Featured review

"Perfectly appointed Cape Coral Vacation Home"

The owners of this home fully understand what the VRBO customer is looking for. Everything you need to make a home rental feel like a home is in the house. Upon arrival, everything was spotless, and we...

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$233
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Located in beautiful Siesta Key, Fl. this bayside condo is full of amenities needed for a relaxing beach vacation. Two tennis courts with Pickleball available, two heated pools, covered private parking, outdoor gas grills, boat docks, outdoor bathrooms within this private, gated community.Walk to...

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Featured review

"Fantastic"

Very family friendly, had beach toys and beach towels available, along with a beach tote. Host provided us a pack and play on request. Beautiful bay facing condo and easy walk to gulf side.

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$200
avg per night
Ave Maria Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 35 miles to Naples and Vanderbilt beech

Key Amenities

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

About this property

luxury living with this exquisite Diangelo II second-floor unit, nestled within the prestigious Ave Maria Nation Golf and Country Club. This 2-bedroom, 2-bathrooms plus Den has a sleeping option and office space residence offers a unique blend of sophistication and comfort, all set against the backdrop...

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Featured review

"Great Place"

We had a wonderful time at Ashok’s place at the National, Ave Maria. The condo is well kept and clean. We did stay for 3 months and found that a few things were needed for a long stay. Ashok met our...

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$233
avg per night
Fort Myers Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
19 reviews

Key Amenities

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

About this property

Hurricane Ian (2022) damaged the Estero Beach Club. Repairs are now nearing completion and the Club will once again be a wonderful, unique, vacation spot We should be able to accept reservation in the near future Pool repairs may not be completed by then. PLEASE NOTE: The pictures now showing are...

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Featured review

"Beautiful"

Great condo, great beach. It’s a lovely area to be at. Will be returning for sure. All amenities are within walking distance

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$215
avg per night
Port Charlotte House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Discover the allure and convenience of this stylish 3BR 2BA oasis in the lovely neighborhood of Port Charlotte, FL. Indulge in a luxurious escape with an elegant interior, entertaining and comfortable amenities, and much more, just a short distance from sun-soaked beaches, renowned restaurants, shops,...

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$178
avg per night
Last Minute Deal
Bradenton Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This beautifully updated condo offers a serene and spacious escape with stunning sunset views from the balcony. The unit features a king bed in the master bedroom and two double beds in the guest room, making it perfect for families or groups. The large windows bring in plenty of natural light, creating...

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$451
avg per night
Punta Gorda Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Lease this Luxury Birkdale, 2-bedroom, and 2-bathroom, on the desired top floor of the Terrace Condominiums; located in the beautiful, secured with gated entrance at Heritage Landing.Heritage Landing is a brand-new Golf Country Club Community in the beautiful Punta Gorda, Florida. Current amenities...

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$185
avg per night
Naples House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Escape to our stunning, custom-built pool home and experience the ultimate in relaxation and comfort. Nestled in a prime location, just minutes from world-class shopping, dining, and pristine beaches, this vacation rental offers the perfect blend of style, convenience, and tranquility. Step inside and...

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$584
avg per night
Naples Condo
Sleeps 2, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 10 miles to Naples Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Discover your slice of paradise just 10 miles from Naples' pristine beaches! This beautifully remodeled 1-bedroom condo is nestled in a charming gated community, close to first-tier shopping, dining, and world-class golf courses.Step inside to find a modern open-concept kitchen with new appliances...

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Featured review

"Convenient and quiet condo"

This condo is well located in close proximity to Naples downtown and local beaches. I stayed here during a work contract and found the hospital to be conveniently located for commuting. The neighborhood...

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$90
avg per night
Marco Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beautiful 2 bedroom, 2 bath recently updated condo located on the south end of the Island at the Essex Condominium. The condo is well appointed with a king bed in the master with in-suite bathroom with walk-in shower and dual sinks. The guest bedroom has 2 full beds and an adjacent bathroom with single...

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$251
avg per night
New
Punta Gorda Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

Resort Living at Its Finest!Fully furnished, turnkey monthly/seasonal rental available in the exclusive Heritage Landing Golf & Country Club. This highly sought-after 2 bedroom, 2 bathroom Birkdale floor plan offers a bright, spacious open-concept layout with quartz countertops, stainless-steel...

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$163
avg per night
Cape Coral Villa
Sleeps 60, 3 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Beautiful and modern “Doll House”. Awesome Swimming Pool with a vanishing edge and integrated Hot Tub. Featuring 3 bedrooms and 2 full bath, great location on a unrestricted Gulf Access canal 2 minutes from the River. Truly a Boater’s Dream.PLEASE NOTE.... the correct address is...

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Featured review

"Fun in the Sun"

Had a great time. House was wonderful and Remy was very responsive. Pool area was amazing and house location was quite and close to everything.

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$256
avg per night
Fort Myers House
Sleeps 8, 4 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Just minutes from SW Florida's award-winning beaches, shopping, dining, golf and professional baseball you will find the gated golf community of Crown Colony. As a seasonal guest, you will have access to the clubhouse and other desired amenities including tennis, fitness center, heated community...

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$201
avg per night
Englewood Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Charming Old Florida Condo…Minutes to World Famous Beaches. 2 Bedroom, 2 Bathroom Condo in Active Adult Community with Pool. Spacious Condo with plenty of room for 4 with screened in porch and all the necessities for a short vacation or a seasonal stay!

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$114
avg per night
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

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

About this property

first floor classic coach home with secluded garden viewThis brand new first floor condo, a West Indies Style Architecture recently completed will impress as it features ceramic tile flooring throughout, beautiful appointed cabinetry and a beach-driven color palette. Pets are permitted with prior...

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$224
avg per night
Cape Coral Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Our air-conditioned Seaside Villa The Sanibel not only impresses with its south-facing orientation, but also with its bright and friendly interior design. From the first day of your vacation, you will never forget the beach feeling. In the living area there is a TV incl. Sonos sound system where you can...

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Featured review

"An unbelievable, memorable experience"

I’m a mom/wife. I work for the United States government as a Federal Marshal. My job carries a great amount of stress and responsibility. For me to be able to give this vacation to my two beautiful boys...

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$338
avg per night
Marco Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Gorgeous inland home with beach access

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$439
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

2 bedroom + Den and 3 bathrooms with views of the Beach of Longboat Key. Prestigious entrance to the Pierre through the lobby with a concierge doorman to great your guests as they arrive to visit. This unit offers 2 balconies to relax on and enjoy the view of the sunset or calm waters of the Gulf of Mexico....

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$416
avg per night
Sarasota Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 1 miles to Siesta Key

Key Amenities

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

About this property

OUR RATES:June-November 2025 $2250 December 2025 $3000 January 2026 $4500 February 2026 $5000 March 2026 $5000 April 2026 $3000 May-December 2026 $2250*Calendar...

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Featured review

"Great stay at Oasis on Osprey"

It was a pleasure working with Ana (and her husband). The unit was clean, modernized, and comfortable. The area was very nice, quiet, friendly neighbors and kept clean. Location was good, plenty of restaurants...

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$145
avg per night
Naples Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

**Recently renovated - bedrooms, bathroooms, kitchen**Gorgeous, highly-desirable 2 bedroom 2 bath with lake and golf course views located on the second floor. This fantastic condo is in the highly desirable North Naples community of Cypress Woods Golf and Country Club, a very active Golf Community. In...

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$108
avg per night
Sarasota House
Sleeps 7, 3 bedrooms, 3.5 bathrooms
3 reviews

Key Amenities

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

About this property

Our 3 bedroom, 3 1/2 bath beach house is located on Siesta Key and is on the gulf side of Beach Road. Our home is a standalone unit on 3 levels with 2 decks, a ground level patio, with a on e car garage. We are directly on Crescent Beach with gulf views and have a private access to the beach. It is...

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Featured review

"Well taken care of beach front rental."

This house was great for our family. It was right on the beach and walking distance to town. It was clean and I don’t think we saw a bug inside the whole time. Great communication with the owner as well....

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$388
avg per night
Cape Coral Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 7 miles to Yacht Club Cape Coral

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The Villa Allegra has been newly renovated and furnished in 2012 and has room for six people with three bedrooms and two bathrooms. Also, the living and dining area, and a bright typical American kitchen are perfectly equipped.The most beautiful is the stay on the spacious pool terrace, which invites...

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Featured review

"Pleasant winter getaway"

We enjoyed our stay at the house. It was clean, comfortable and had many amenities to use. The pool was wonderful and the colorful lighting made it fun to swim at night. The only downside was the television...

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$206
avg per night
Naples Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

About this property

This 2b/2b + Den condo sits right on the Cypress course at Heritage Bay. Equipped with everything you need for the perfect getaway and close to fine Dinning exclusive shopping and world class Beaches this is a Golfers Paradise.Heritage Bay is an upscale-gated community with a championship 27 hole...

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$283
avg per night
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