Smoking-friendly holiday rentals in Lee County

An aerial view of a spacious home features a heated infinitive pool and hot tub, surrounded by lounge chairs on a patio. A private dock accommodates a boat, with manicured lawns and tropical landscaping completing the outdoor setting.

5 out of 5 average rating, 35 reviews

Waterfront Cape Coral Oasis+ Heated Pool | Kayaks

This Spacious 4-bedroom 3 Bathroom home was tastefully designed for relaxation and adventure, perfect for families, boaters, and vacationers. Bring your own boat and take advantage of our private dock or explore the water with the provided kayaks. Unwind in the heated pool and hot tub. Enjoy amazing outdoor furniture and outdoor kitchen. Inside, enjoy modern finishes, ice-cold A/C, Super fast WiFi and a fully stocked kitchen with all the essentials. Each bedroom features a 65-inch Samsung TV

5 out of 5 average rating, 5 reviews

Boaters Paradise: Private 1/1 with FREE parking!

Escape to your own peaceful slice of Southwest Florida! This cozy 1-bedroom offers everything you need for a comfortable, laid-back stay — just 1 mile from the famous Matlacha Bridge, known as “The Fishingest Bridge in America!” Perfect for solo travelers, couples, or boaters, this unit features a full kitchenette, private bath, and comfortable living area. You’ll also have access to FREE onsite parking for boats, trailers, RV's, etc. and be close to three public boat ramps within a mile.

4.96 out of 5 average rating, 85 reviews

Home in Fort Myers

Bohemian Bungalow / Washer + Dryer / Private

Your family will be close to everything when you stay at this centrally-located place. Stylish, yet comfortable - You have access to an additional spacious sun patio, a washer and dryer, and ample back and front yard. 10 miles to the beach, biking distance to Historic Downtown Fort Myers, this home is a renovated blast from the past. Terrazzo floors throughout kept the original Florida charm. The most peaceful neighborhood with walking distance to a restaurant with indoor/outdoor dining.

4.88 out of 5 average rating, 43 reviews

Apartment in Sanibel

The Flamingo Residence at Sandpiper Inn

The Flamingo Residence is a one bedroom, one bath, unit located in the newly renovated, Sandpiper Inn. Festooned with gorgeous palm trees and an ever present ocean breeze, The Sandpiper Inn has been coveted by travelers as the most colorful inn on Sanibel. Close to beaches, dining and shopping, this property boasts one of the best locations on all of Sanibel Island. NEW: dog enclosure for our 4-legged guests to play while you enjoy our outdoor seating areas with grill and fire pit!

A spacious outdoor area is enclosed by a screened lanai, featuring a heated pool and spa. Lush tropical plants and colorful flowers are arranged around the poolside, while the clear sky and palm trees are visible in the background, enhancing the serene atmosphere.

4.88 out of 5 average rating, 25 reviews

Cornwallis Escape

Welcome to sunny Cape Coral! At Cornwallis Escape, enjoy an AMAZING HEATED POOL with sun on the lanai all afternoon. Grill out, relax, or head 30 mins to Fort Myers Beach—beach gear included! Stay 4+ nights for FREE waterpark passes. Equipped with a BOAT LIFT and 2 JET SKI LIFTS, rent a craft nearby to explore the Gulf. Fresh coffee is ready when you arrive, and you're just 35 mins from the airport. Everything you need, nothing you don’t—just sunshine, water, and pure relaxation!

A spacious lanai features a heated saltwater pool surrounded by lounge chairs, each equipped with rolled towels. The screened enclosure allows for an unobstructed view of the canal and surrounding area, while decorative string lights add ambiance above.

5 out of 5 average rating, 35 reviews

Sunny Days-Canal Home w/pool & spa

Relax with the whole family at this peaceful place to stay which features: *2200 Sq. Ft *10-foot windows and doors *Private large, screened in Lanai *Large heated SaltwaterPool & Spa *Outdoor kitchen, living room w/TV, and dining area *Fully stocked and equipped Kitchen *Nespresso Coffee Machine *Off street parking, driveway will accomodate 2 vehicles *Safe Neighborhood *On the canal. Room to tie up a boat or two *1 walkable Mile to coffee shops, and several restaurants

An open living area is depicted, featuring light-colored leather sofas arranged around a central coffee table. A ceiling fan hangs above, and a large television is mounted on the wall. Dining space is visible in the background with a round table and decorative mirrors.

5 out of 5 average rating, 16 reviews

Southwest Cape Coral like new 3 bed 2 bath home

This is a great 3 bedroom 2 bath home in like new condition with all brand new furniture ready for you to relax in. This home is located in Southwest Cape Coral close to shopping, great restaurants, 27 hole golf course at Cape Royal. Located in a quiet neighborhood on an oversized 3 lot site with a huge private fenced back yard. Home has Wifi, cable TV, full lawn maintenance you do not need to do anything just bring your clothes and toothbrush everything you need is here.

4.99 out of 5 average rating, 210 reviews

A serene waterfront scene features two small boats gliding through calm waters, surrounded by lush palm trees. Nearby structures exhibit a mix of colors, with a sailboat anchored in the background, creating a peaceful atmosphere in the canal.

Home in Matlacha

Matlacha Paradise! NEW Waterfront Home-Free Kayak

Matlacha is for LOVERS! Lovers of relaxation, fishing, art, friends, social scenes and enjoying Life in a beautiful location ON THE WATER! Matlacha had damage from Ian. Our new home - none. You can still walk to great restaurants, shops and the fishing bridge. Enjoy the water in Matlacha & the Barrier Islands. Use our 1 person kayak for fun or fishing from our 8'X22' FUN & SUN deck docked in the back canal with picnic table & loungers. Relax, sun, grill and fish.

4.84 out of 5 average rating, 138 reviews

A spacious outdoor entertaining area is highlighted by a hot tub and a saltwater pool, both surrounded by mesh screening. A large dining table with multiple chairs sits shaded beneath the ceiling fan, complemented by decorative string lights for a cozy ambiance.

Home in Lehigh Acres

LIVING in PARADISE 🌴 ⛱️ 😎

Hotel accommodations with the comforts of home! Clean and beautiful house. Hot tub and pool, full grill Gazebo,patio for cookouts. Beautiful living room area, with a TV and family space. Dedicated dining room space, equipped with everything needed with a spectacular dinner. Kitchen is fully equipped. King , two queen beds. Beautiful full bathrooms. Close to Downtown Fort Myers, Bell Tower Shops, and Fort Myers Beach.

5 out of 5 average rating, 7 reviews

A spacious pool area is enclosed by a screened lanai, featuring a large heated pool. Lounge chairs are positioned alongside the pool, and a dining set is visible in the covered outdoor area. Lush greenery and water views provide a serene backdrop.

Villa in Cape Coral

Intervillas Florida - The Barefoot Oasis

Kick back and relax in this calm, stylish space.Escape from everyday life and enjoy the luxury of an upscale resort. Villa Barefoot Oasis was built in 2021 and is furnished very bright and modern. It is located in SW Cape Coral near restaurants, attractions and beaches. The home features a large, heated canal pool and patio with a beautiful outdoor area where you can be pampered by the Florida sun all year round.

5 out of 5 average rating, 9 reviews

Apartment in Fort Myers

King Studio Close To Beaches, Trails and History!

Cozy studio with a king-sized bed and organic cotton linens, pristinely clean and inviting. Enjoy a lush tropical yard with vibrant plants just steps away. Minutes from beaches, FGCU, RSW Airport, nature trails, and historic sites. Ideal for couples, solo travelers, or anyone seeking a comfortable, serene getaway with easy access to Fort Myers’ best spots. 🌴✨ The most central spot of SWFL you can book!