Vacation rentals with a pool in Bokeelia

Boater’s Paradise in Bokeelia!

Welcome to Bokeelia! Forget your worries in this spacious and serene space. Beautiful Newly Remodeled Home located right On the Water with Boat Lifts & Dockage, and plenty of parking for All Come and enjoy a Relaxing and Comfy Home. Boaters! We are across the street from the Public Boat Ramp, Minutes to Captiva & Sanibel Islands, Cayó Costa, Cabbage Key, and Boca Grande which is known for its sugar sand Beaches. Best of all, Amazing Fishing in Florida aka “Tarpon Fishing Capital of the World!”

Family · Location · Access

Antigua Cay Retreat

Stylish and classy, with plenty of space to relax and enjoy one of Floridas most unique and special hidden treasures. Bokeelia on Pine Island! Beautifully remodeled home has 3 full bedrooms, as well as a bonus room with double futon downstairs at pool lanai. Lots of outdoor space around the pool, on the new boat dock as well as an upper level outdoor breakfast area that can be fully opened up to both main bedrooms via the oversized sliding glass doors to each bedroom. Also includes an elevator!

Family · Location · Grill

Pine Island Pelican Suite: privacy, pool, gardens

Welcome to the Pelican Suite! Secure, private entrance, king bed, outdoor kitchen and patio. This suite is totally separate from the owners' home/upstairs. Adults only. King bed, ensuite private bathroom with shower; AC. WiFi, cable, TV. Exclusive use of ground floor screened guest lanai: kitchen, fridge, BBQ. Beautiful gardens, small/secluded heated pool. Free parking. The Pelican Suite is ideal for a relaxing no-stress break in the sun! We welcome guests who prefer a low-key getaway.

Family · Location · Indoor spaces

Blue Laguna - Vacation in paradise!

This bright, fully equipped welcoming three‑story home features a private heated pool and a rooftop observation deck with stunning 360‑degree water views. It offers three comfortable bedrooms and three full bathrooms for up to six guests, plus two screened lanais where you can relax in the island breeze and listen to the birds. A four‑seater golf cart is included, so you can easily explore the beaches and sandy paths of beautiful North Captiva Island. Also full access to Island Club amenities!

Value · Family · Solo travel

Romantic Getaway “Waterside” Dockage~Canal front

Also available: airbnb.com/h/aframeausable Minutes to open water and Jug Creek Marina! Wait till you see this freshly updated cottage! Bring your boat, or rent one nearby. There is a dock available here. Tarpon capital of the world, and Charlotte Harbor moments away! Boca Grande, Cayo Costa, Useppa, North Captiva, Sanibel and Cabbage Key, etc. a short boat ride away! The golf carts/kayaks/boats/bikes are available to rent at local resources! Jug Creek Marina is steps away with food & music!

Location · Beach · Getting around

Private Paradise on Pine Island

Wake to soft island breezes and golden sunlight, sip coffee on the spacious screened porch, then slip into your own sparkling private pool with soothing fountain, fully enclosed for privacy. This bright three-bedroom retreat offers open living, soaring ceilings, a beautiful chef’s kitchen with oversized island, split bedrooms, and shaded outdoor space perfect for gathering. Walk to parks and shops, explore nearby beaches and boating, and savor the true charm of peaceful Old Florida living.

Location · Family · Check-in

Charlie's of Bokeelia

Enjoy sun-filled days and serene sunsets at this peaceful Bokeelia retreat on the canal. Relax by the saltwater pool with mangrove views for privacy and tranquility, located on a quiet cul-de-sac. The three spacious bedrooms, all with smart TVs, include two open to the patio. The open-concept home seamlessly connects to the patio, and the fully stocked kitchen is perfect for a wonderful family or romantic dinner. Plus, take a quick ride out to the open water to wherever you decide.

Family · Location · Outdoor spaces

Waterfront Fisherman’s Retreat Quick Harbor Access

Welcome to your perfect Pine Island getaway! This charming 2-bedroom, 1-bath canal-front home is an ideal escape for fishing lovers, boaters, and anyone looking to relax in a peaceful island setting. Located on a quiet canal, the property offers direct access to Charlotte Harbor within minutes, making it easy to reach open water for fishing, boating, and exploring. Our private boathouse and lift are currently occupied, but guests who rent a boat are welcome to tie up at the dock.

Family · Location · Outdoor spaces

​Boater’s Paradise: No-Bridge Gulf Access & Pool

⚓ Direct Gulf Access (No Bridges): Cruise to open water! 🏊‍♂️ FREE Heated Pool: Waterfront views, zero daily heating fees. 🛏️ Group Oasis: 4BR | 3BA | 7 Beds (Sleeps 13 comfortably). 🎣 Outdoor Living: Fish from your dock, BBQ & spectacular sunsets! 🐾 Pets Welcome & Fast Wi-Fi! 🚙 Massive Parking: Room for boat trailers! 📍 Location: Heart of Matlacha, minutes to Cape Coral. ⚡ Prime season dates book fast. Lock in your direct water access and reserve your dates today.

Family · Location · Cleanliness

Charming 2-BR Home w/ AC, Dock & Peaceful.

Discover this charming 2-bedroom waterfront home in peaceful Saint James City. Each bedroom features a comfortable queen bed, plus a cozy living room with a sofa bed for extra guests. With 2 full bathrooms, everyone enjoys space and privacy. The home offers air conditioning and heating for year-round comfort. Relax indoors, unwind by the water, or plan your next island adventure from this inviting home away from home. We’re always happy to share local recommendations.

Location · Decor · Biking

Bokeelia Breeze - Boater's Dream

Discover paradise at Bokeelia Breeze on a Gulf access canal! This stunning Bokeelia vacation rental offers boaters the perfect getaway with a heated pool, wrap-around deck, private dock fishing, and breathtaking 360-degree views from the third-floor sanctuary. Located on quiet Pine Island with easy marina access to Charlotte Harbor. Modern amenities, beautiful grounds, and three bedrooms make this your ideal Florida retreat. Your bucket list adventure starts here!

Location · Family · Pool

Salt Life Serenity

Canal front property, pet friendly, complete with pool, jacuzzi, and boat dock. 2 King beds with 2 full bathrooms. Den/tv room that pulls out into a comfortable Queen bed. We pride ourselves on having a fully stocked kitchen with multiple coffee makers to make your stay in this newly renovated home one to remember. Enjoy fishing from the dock or watching the manatees as they move with the tides.

Location · Family · Comfort