Vacation rentals with a pool in Windley Key

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Windley Key

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Guest favorite

Condo in Tavernier

4.95 out of 5 average rating, 110 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

Guest favorite

Condo in Tavernier

4.96 out of 5 average rating, 164 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Guest favorite

Condo in Tavernier

4.88 out of 5 average rating, 231 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 38 acres and one side is surrounded by a nature preserve.

Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 188 reviews

Casa Mariposa: Easy walk to Sombrero Beach

***SUMMER SALE*** Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated by Forbes the #1 Airbnb for couples south of Orlando for 2024 and a top 10 Airbnb in Florida. Step from your private suite to our 50' chilled lap pool surrounded with swaying palm trees and tropical foliage, large coral stone patio, and extensive tropical gardens. Avoid beach parking fees at beautiful Sombrero Beach with a short stroll from your suite at Casa Mariposa!

Guest favorite

Condo in Tavernier

4.94 out of 5 average rating, 141 reviews

It's Tiki Time in the Keys! Mid-Mod 1 Br/1Ba

Stay at our tropical hideaway rated one the “Coolest Airbnb’s in the Keys” by Trips to Discover! Our romantic condominium (sleeps 4) is located at the gated Ocean Pointe resort in the nature isle of Tavernier. You'll love the colorful mid-century modern decor that reflects the shades of this Keys paradise in the American Caribbean. With 60+ pristine acres, Ocean Pointe is the perfect blend of natural beauty and modern-day luxury and convenience for a great couples or small family getaway .

Guest favorite

Rental unit in Key Largo

4.94 out of 5 average rating, 252 reviews

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi

Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

Guest favorite

Cottage in Key Largo

4.96 out of 5 average rating, 149 reviews

Charming Key Largo Cottage on the Water w/Kayaks!

Charming "Tiny House" Cottage on a main canal just two units from open water. Amazing location for boaters, fisherman and alike. This is a quaint and close knit RV park where you can keep to yourself or wander around and enjoy happy hour with new local friends. Bar none the best kayak, paddle board and fishing area. Two Tandem (each kayak accommodates two people) Kayaks and two paddle boards included in rental. Great outdoor space to dock your boat, fish off of or enjoy a few cocktails!

Guest favorite

Condo in Key Colony Beach

4.96 out of 5 average rating, 179 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Guest favorite

Condo in Tavernier

4.99 out of 5 average rating, 106 reviews

Ocean View Corner Penthouse | Ocean Pointe 5416

Coastal decor greets you in this serene Penthouse unit with all around views of the Atlantic ocean. This end unit is located in fabulous Ocean Pointe Suites, complete with small beach, pier, marina, large pool, jacuzzi, tennis and pickle ball court and even basket ball hoop. This unit is smack dab in the middle between Key Largo and Islamorada in the Florida Keys. Very close to amazing waterfront dining, snorkeling, diving, fishing, paddle boarding and kayaking. Must stay to believe!

Guest favorite

Condo in Tavernier

4.98 out of 5 average rating, 149 reviews

Ocean Views at Ocean Pointe

Conveniently located at MM 92.5, approximately 1 hour drive from Miami, you can enjoy a modern, newly redecorated Keys escape with amazing views of the sunrise right from your oceanside balcony. 2 bed/2 bath with full kitchen and washer/dryer. Pool, beach, pier, BBQ area, and private boat marina within this private community. Kayaks, paddle boards and bikes available for rent. No need to leave, but grocery stores, spas and ample restaurants are close by to fill any need.

Superhost

Villa in Marathon

4.9 out of 5 average rating, 167 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Guest favorite

Condo in Key Largo

4.98 out of 5 average rating, 120 reviews

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike

Enjoy a Key Largo adventure in our deluxe oceanfront condo WHICH INCLUDES 2 KAYAKS, 2 PADDLEBOARDS, 2 BIKES, TENNIS RACKETS/BALLS AND FISHING GEAR in a private beach resort community with a fishing jetty, a 24/7 boat ramp & a 3-acre salt-water lagoon for swimming, snorkeling, kayaking & paddleboarding. The condo sleeps 6 & is in the gated Kawama Community of Key Largo, surrounded by JOHN PENNEKAMP CORAL REEF STATE PARK. Marina boat slips may be available for rent.