Holiday rentals with outdoor seating near Caspersen Beach

Tiny home in Port Charlotte

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

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

Flat 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

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.

4.98 out of 5 average rating, 141 reviews

Heated Pool Oasis 3BR/2BA near Siesta Key Beach

Relax at this modern heated pool house located just 15 min from the famous Siesta Key Beach. Nested in a quiet neighborhood with a lot of privacy, the house has plenty of space for an entire family or a group of friends. An additional family room with a TV for kids. Relax by the pool in the spacious outdoor area or explore the beautiful downtown filled with restaurants. Recently renovated, this home offers handmade authentic Mexican tile flooring to compliment a cozy and contemporary design.

Superhost

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.

4.96 out of 5 average rating, 124 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!

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.

5 out of 5 average rating, 9 reviews

Guest house 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

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

Campervan/Motorhome 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.