Vacation rentals with outdoor seating near Caspersen Beach

Tiny home in Port Charlotte

Two individuals are seen kayaking on a calm body of water, surrounded by lush greenery. Bright, warm sunlight reflects off the surface, while orange paddles create ripples as they navigate their kayaks. The scene emphasizes an inviting outdoor adventure atmosphere.

5 out of 5 average rating, 6 reviews

Minutes to Sand, Dog Friendly, Hot Tub Luxury

Watch the stars from your hot tub! Not camping, not glamping... This is luxury living for less! Private dog friendly property. Hooked up to city water, cold air in all rooms, immediate demand hot water and septic. This slice of paradise is minutes from the sand and has an elegantly appointed private master, two private loft bedrooms, sleeper sofa & 9' vaulted ceilings. Your private retreat includes the use of two kayaks, gazebo, beach chairs, 5G Wi-fi & Netflix, Prime, Paramount. Paradise!

5 out of 5 average rating, 13 reviews

An outdoor dining area features a wooden table surrounded by black wicker chairs, positioned on a patio overlooking a canal. The scene is enhanced by greenery, trees, and the bright sky, creating a serene setting for meals or gatherings.

Home in Port Charlotte

Waterfront Escape on canal ocean access kayaks

This stylish waterfront home is perfect for group trips. This four bedroom two bath home has room for two families to fit comfortably. It has a variety of seating both indoor and outdoor to accommodate your stay. There is room to spend time together or find your own little quiet area. The home is located only minutes from the beach, pool, boat launch and fishing pier. Close to multiple waterfront restaurants and shopping. Only minutes from Sunseeker Resort, area boat tours and fishing charters

Superhost

A bright studio apartment features a spacious bed dressed in light grey linens. Two bedside lamps provide soft illumination. A small kitchenette is visible, while a doorway leads to a bathroom with modern fixtures. Natural light enters through a door leading to the private patio.

Apartment in Siesta Key

4.77 out of 5 average rating, 104 reviews

Gertrude's Siesta | Patio & 1-min to Beach/Village

The Village Studio Top location on island! Apartment with full kitchen, private patio, gated courtyard, in world famous Siesta Village! Leave the car behind and walk to white-sand beaches, 20 bars and restaurants, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Experience a combination of fun ease and relaxation you can't get in other vacations! Book a special getaway now! - Tollbooth by AirbnbCorpMiddlemen, but this property is from GertrudeRentalsSiesta

The exterior of the villa is framed by lush palm trees and vibrant foliage, offering a tropical ambiance. A wide porch with seating faces the street, while a gravel driveway provides access to the entrance, creating an inviting approach to the home.

4.91 out of 5 average rating, 211 reviews

☀ Villa & Garden in Downtown ~ 5 Min to Beaches

Our coastal chic, contemporary Sun Villa is situated in Sarasota’s charming downtown historic neighborhood of Laurel Park. The villa's garden hideaway is a real Floridian oasis, complete with fire pit and sun loungers. Downtown and all its restaurants, bars and shops is just on your doorstep. Plus 3 sugar white beaches – including Siesta Beach one of the most beautiful beaches in the world – are only a 5-min ride away! We’ve poured our hearts & souls into this villa, it's our family business.

Superhost

A refreshing swimming pool is framed by a well-kept lawn, with several lounge chairs positioned nearby. A shaded gazebo is equipped with dining furniture, under a bright red umbrella. Lush tropical plants and vibrant flowers enhance the serene atmosphere.

Campsite in Sarasota

4.79 out of 5 average rating, 29 reviews

Siesta RV & Tent Resort (2 of 5 sites)

This natural, yet manicured 1/2-acre venue includes all the premium amenities of a 1st class camping/RV resort. As a private enclave, we excel in providing a more intimate, cleaner and exclusive camping experience only minutes from world-famous Siesta Key Beach. Our reviews say it all. Our tropical oasis also offers premium extras not found anywhere else, including: a large pool, portable a/c or heating units, a mini-frig, microwaves, coolers, beach accessories, bike rentals and many more.

An indoor pool is enclosed within a screened area, offering a clear view of tranquil blue water and surrounding trees. Comfortable outdoor seating is visible, complemented by a sunlit patio space. Large glass doors provide access to the pool area, enhancing the open feel.

4.96 out of 5 average rating, 123 reviews

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

A well-maintained vacation home is surrounded by lush greenery and palm trees, set against a clear blue sky. A gravel path leads to the entrance, where inviting seating is visible on a covered porch, creating a welcoming atmosphere for guests.

4.86 out of 5 average rating, 7 reviews

Sunshine Awaits- Heated Pool Home! 6 min to DWTN!

Escape to your own private Sarasota oasis! This 3-bed, 2-bath vacation home boasts a heated pool for sun-soaked days & unforgettable evenings under the stars. Find a fully-equipped kitchen, comfy living space, Smart TVs, & free WiFi. Included are a gas grill & board games for poolside BBQs & family fun. Close to local shops, restaurants, & parks. World-famous Siesta Key Beach & Lido Beach are a short 15 min away, along with a 10 min drive to vibrant downtown Sarasota & its cultural scene.

Camper/RV in North Fort Myers

The image presents a tranquil waterfront setting with calm waters reflecting the sky. A floating dock is visible, equipped with paddle boards, while a boat is moored nearby. Lush greenery and a hammock enhance the outdoor space, highlighting a peaceful retreat atmosphere.

4.95 out of 5 average rating, 57 reviews

Waterways Escape

The intercoastal waterways is literally your backyard with the view of downtown Fort Myers across the Caloosahatchee River. You’ll treasure your time at this memorable place. Fantastic location, only 10 minutes to many restaurants, events and shops in Downtown Fort Myers. Waterways Escape is a quiet, secluded Paradise, one of a kind water front RV retreat that offers relaxation and activities like kayak, SUP board, fishing snook, redfish and you are welcome to bring your jetSkis or boat.

5 out of 5 average rating, 9 reviews

A comfortably arranged living area features a light green sofa adorned with yellow and white checked pillows. A wooden coffee table sits nearby, surrounded by potted plants. A dining table for four is positioned near large windows that allow natural light to fill the space.

Guesthouse in Bradenton

Serenity Lake Too!

Keep it simple at this peaceful and centrally-located place. 15 minutes from beaches this lovely apartment sits on a pond full of fish with a dock. Large pool ready for swimming and sunning. Charcoal and gas grill available. Beautiful upper deck to sit and enjoy the large mango tree and view over the lake. Golf cart available for evening rides. There is a large driveway for a boat. Swim and fishing accessories available. Minutes from I-75 - also near the famous Lakewood Ranch downtown.

4.96 out of 5 average rating, 107 reviews

Colorful swinging chairs are suspended from a wooden frame in a lush backyard. A small round table rests on the deck beneath a cloudy sky, surrounded by greenery and a fenced perimeter.

Home in Nokomis

Cute Little Getaway

Close to the beach and walking distance to 5 restaurants, including one on the water. Our place is less than 2 miles from Nokomis Beach! We have you covered on beach equipment, wagon, chairs, towels and umbrella. The backyard boasts a relaxing, beautiful escape with resort style touches. We have a gas grill to cook your catch, a high powered outdoor fan, and comfy seating in the shade. The house is freshly modernized, open and airy. You will enjoy an outfitted kitchen.

Superhost

A sleeping area is equipped with a cozy bed topped with a vibrant blanket featuring a camping theme. Two patterned pillows rest against the neutral wall. A small table with a black chair is positioned nearby, and an air conditioning unit is mounted above.

Camper/RV in Port Charlotte

4.8 out of 5 average rating, 5 reviews

Entire Rv with BBQ and Patio.

Escape to a charming and comfortable RV getaway, perfect for a relaxing retreat! This cozy RV is fully equipped with all the essentials, offering a unique stay with modern comforts. Step outside to enjoy your private patio, complete with a BBQ grill—ideal for outdoor cooking and unwinding under the stars. Located in a peaceful setting, this space is great for solo travelers, couples, or small families looking to experience the outdoors with a touch of home.