Vacation rentals in Pineland

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Top-rated vacation rentals in Pineland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A screened-in outdoor space features a sparkling pool, surrounded by paver stones and tropical plants. Two loungers are positioned nearby, providing a comfortable area to relax. Sunlight filters through, casting soft shadows across the patio.

Apartment in Fort Myers Beach

4.99 out of 5 average rating, 70 reviews

Island Sunshine Poolside Gem

Important Note: This apartment has been totally remodeled from hurricanes in 2024. Everything is perfect here. Beaches are beautiful, pool is relaxing and welcoming. Thankfully the island restaurants and bars are also back up and going in fun island style! Perfectly remodeled bright and cheery poolside apartment. This one truly has it all. From luxury bedding to a fully equipped kitchen to a spacious screen porch right outside the living room door. This dreamy island apartment offers a king me

Top guest favorite

Home in Bonita Springs

5 out of 5 average rating, 17 reviews

Casa Bonita by the Sea

Indulge in a dream vacation at our 3-bedroom oasis near one of Florida's top beaches. Inside this brand new home, bask in natural light and chic decor. Unwind on the reclining sofa, step outside to your private paradise with a saltwater pool, infinity spa, and outdoor kitchen. The master suite offers luxury with pool access, soaker tub and shower. Enjoy nearby beach activities, hiking, shopping and dining. Every detail is designed for your relaxation. Book now for the ultimate coastal retreat!

Superhost

A bright kitchen space features a large countertop with bar seating and modern cabinetry. Colorful decor accents the walls, and natural light floods in through windows with ocean views. A stylish light fixture hangs above, contributing to the updated look of the area.

Condo in Captiva

4.65 out of 5 average rating, 68 reviews

South Seas Bayside Villa 5234

Captiva Island Bayside vacation rental condo. Pool, beach, tennis, WiFi. 1 bedroom/2 bathrooms. 2 full beds in the bedroom. Spacious living room, dining area and full kitchen. Everything nicely updated. Private screened lanai with water views of the marina and bay just beyond. Short walk over to the sandy beaches. Rent a golf cart and get around the resort easily as well as nearby shops and restaurants. Full resort access not available. Association pool, hot tub, nearby beach always included.

Top guest favorite

A screened patio area features a round dining table with four chairs, overlooking a large heated pool and scenic water views. The floor is designed with decorative stone patterns, and a ceiling fan with light is positioned above the dining space, enhancing comfort and airflow.

Home in Punta Gorda

5 out of 5 average rating, 15 reviews

Sensational! Sunny, Heated Pool

**NEW LISTING/HUGE DISCOUNTED PRICE*** LUXURY PGI home; 1.5 mile/5 minute distance to Fisherman’s Village and attention to detail with remodel and brand new furnishings. Take advantage of tremendously discounted Prime dates available in 2024 AND 2025 Winter Season. Check PREMIER HOST reviews averaging 5.0 on other site.

Superhost

A spacious bedroom features a large bed with a patterned quilt and a flat-screen TV. Expansive windows provide stunning views of the ocean and surrounding greenery, allowing natural light to fill the room. A ceiling fan adds to the comfortable ambiance.

Home in Captiva

4.95 out of 5 average rating, 92 reviews

Ocean Views |Fast WiFi & Pool |5 Min Walk to Beach

❤We have OVER EIGHTY 5★ Reviews......Book with Confidence❤ ★ 2 Story, 2,115 Sq Ft Home w/ 2 Patios ★ Views of the Ocean on 2 sides ★ 5 Min Walk to Gulf of Mexico Beach ★ Sleeps 8 - (2 Kings, 2 Twins, Sofa Bed) - 3 Bathrooms ★Fast Wifi, Keurig, & Smart TVs ★ Access to Pool, Hot Tub & Grill ★ Pack N Play + Board Games ★ Experienced Hosts - (easy check-in, clear communication, recommendations, clean home) ★★ 3 hurricanes hit the area over the last 2 years but the area is coming back nicely★★

Superhost

Condo in Bonita Springs

4.93 out of 5 average rating, 67 reviews

Bonita Springs/Gulf View 9th Floor/steps to Beach!

Gulf Views of Bonita Beach Coastline from your 9th Floor Lanai! -One from the Penthouse -Beautiful Beaches -Sunset Just Across the Street!!- On the beach Every Night- Everything included for an Amazing Stay- including -Beach chairs ,Umbrella- Free WIFI -Just bring Shampoo and get ready to have some Fun!! A famous bar and grill right on the Beach with your favorite Cocktails and Happy Hour all day long- OUR PRICES ARE DISCOUNTED off season and for longer stays -just send in a request!!

Guest favorite

Cottage in Captiva

4.85 out of 5 average rating, 87 reviews

Cottage Secluded in Palms 1 minute walk to Beach

Actual review left by a Guest “We had a great time in Captiva Island. It's the perfect place to get away for a relaxing, secluded, car-free vacation. Federico's cottage is conveniently located just a short walk to the beach and had all of the amenities we needed to relax and enjoy the trip. Federico was helpful and responsive when I had any questions. I highly recommend staying here if you are looking to disconnect and enjoy pristine beaches with lots wildlife and natural beauty. ”

Guest favorite

Home in North Fort Myers

4.91 out of 5 average rating, 23 reviews

Paradise Found

PARADISE FOUND, you can vacation right here at your own LAKE SIDE PARK! Stunning, peaceful & beautiful waterfront property with your own little island. Fish, bird watch or feed the turtles from your private dock or double arched bridge. Huge back yard for enjoyment & safety of children & pets. Your vacation home has a sunny disposition & soaring ceilings. First floor master suite with sliders to pool/lanai. Two story ceilings in livingroom & gorgeous staircase to guest suites.

Top guest favorite

The kitchen and dining area feature modern appliances and ample granite counter space. A stylish table with seating for four is complemented by a potted plant. The open layout allows for easy movement, with light-colored cabinetry and a black refrigerator providing contrast.

Home in Fort Myers Beach

5 out of 5 average rating, 63 reviews

Coastal Retreat; paradise found!

Welcome to our tranquil retreat, nestled just minutes away from the pristine shores of Ft Myers Beach and Sanibel. Step inside and be captivated by the inviting ambiance of our thoughtfully designed space. The airy living area welcomes you with its abundant natural light, stylish decor, and comfortable furnishings. Relax on the sofa or enjoy the backyard space as you plan your beach adventures. TV's in every bedroom and living room. We look forward to hosting you!

Superhost

A wall-mounted sign features the words 'Welcome to the BEACH' in bold turquoise lettering, set against a white background. Above the sign, a decorative ship wheel adds a nautical touch to the entryway.

Cottage in Fort Myers Beach

4.89 out of 5 average rating, 28 reviews

DEJA BLUE 1000 FT from Beach Great for Families

1000 ft from the beach No car needed!!!! Walk around town or Trolley Best location on beach Perfect vacation spot, beautiful sunsets Newly renovated Close to time square restaurants and shopping. Relax on landscaped palm tree front patio 3 New flat screen tv’s and Brand new stainless kitchen Beach chairs, umbrella and towels are ready to go to the beach Backyard with grill Let’s book and start your vacation!!!!!!!!!!!!!!!!!!!!!!

Superhost

A serene white sand beach stretches along the shore, meeting calm turquoise waters. Gentle waves lapping at the beach create a tranquil atmosphere, with a clear sky overhead. Distant vegetation adds a natural element to the landscape.

Home in Cape Coral

4.67 out of 5 average rating, 123 reviews

La venezia beautiful 4 bedroom pool/spa heated

Nicely decorated big spacious rooms comfortable beds close to great restaurants 10 minutes from cape coral beach and 1/2 an hour from fort Myers beach 10 to sun splash water park and great house just to relax and enjoy great pool and spa Now with covid-19 we are taking all the precautions to completely sanitized all areas using all the right products for all your protection

Superhost

The shoreline is captured, showing gentle waves lapping against soft sand. The clear blue sky meets the horizon, while nearby buildings outline the coastal landscape, indicating proximity to urban amenities.

Home in Fort Myers

4.88 out of 5 average rating, 220 reviews

The Beachy Retreat

This is the ultimate getaway for our guests. Our cozy newly renovated retreat is in the perfect location that is close to the beach, near all the best restaurants, and has all the amenities you will need for a breezy family vacation. Just a short 10 min drive to all the best beaches (Sanibel Island and Ft. Myers Beach), shopping locations, and more!