Accommodation with a pool in Windley Key

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Top-rated rentals with a pool in Windley Key

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Condo in Tavernier

4.91 out of 5 average rating, 111 reviews

500 Burton Drive Tavernier, Key Largo

Renovated suite with 2-bedrooms, 2 full baths located on the 4th floor with ocean and sunrise views, in a gated community. Positioned on the Atlantic Ocean between Key Largo and Islamorada, bordered by protected mangroves and landscaped grounds. The suite has 1 king size bed, 2 singles, with a pull-out sleeper sofa in the living room, accommodating up to 6 people. Full Kitchen, 65" 50" tv's in each bedroom, Wifi and more. We have enhanced our cleaning and added a UV light to the HVAC system.

11 – 18 Dec

$3,649 AUD total

Guest favourite

Campervan/RV in Key Largo

4.94 out of 5 average rating, 228 reviews

New Tinyhouse RV, Kayak, Beach, Fish, Marina, Pool

Newly replaced RV, lot# 19 at Key Largo Kampground and Marina Resort W/ 24 hour security. 1 Queen Bed in loft, Sofa bed, basement, Full Kitchen and Full Bathroom, Cable TV and Wi-Fi. In walking distance to Publix Supermarket, John Pennekamp State Park, deep sea Fishing, Diving and Snorkel Charter boats and first class Restaurants. Private nicely landscaped all-to-your-self lot approx. 26' x 56' and it's, conveniently near the pool, boat ramp w/ trailer parking, laundry area, toilet- bath house

26 Sept – 3 Oct

$2,042 AUD total

Guest favourite

Condo in Tavernier

4.95 out of 5 average rating, 108 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!

21 – 28 Aug

$2,551 AUD total

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 186 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

7 – 14 July

$2,686 AUD total

Guest favourite

Condo in Tavernier

4.96 out of 5 average rating, 159 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.

31 Oct – 7 Nov

$3,370 AUD total

Guest favourite

Condo in Tavernier

4.88 out of 5 average rating, 229 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.

2 – 9 Aug

$3,062 AUD total

Guest favourite

Condo in Tavernier

4.93 out of 5 average rating, 109 reviews

Keys Life Ocean Pointe Pool Jacuzzi Beach Crib

Unique Suite with 2 Balconies that have Unrestricted Ocean Views. The Gem of Ocean Pointe without Doubt. Look at the Photos & Reviews Contactless check-in, go directly to our unit with no standing in line. Come enjoy Key Largo in this Oceanfront condo that is just STEPS from the Pool and Jacuzzi. Onsite Private Beach with Boardwalk & Gazebo. Lighted Tennis Courts with Pickle Ball. Marina & Clubhouse. 24 Hour Manned Gated Resort Bird Watching from Both of your Balconies. Enjoy Life, Key's Life.

11 – 18 Sept

$3,308 AUD total

Guest favourite

Condo in Tavernier

4.93 out of 5 average rating, 136 reviews

It's Tiki Time! Top Floor SeaView 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 .

18 – 25 Aug

$2,914 AUD total

Guest favourite

Cottage in Key Largo

4.96 out of 5 average rating, 147 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!

3 – 10 Oct

$4,216 AUD total

Guest favourite

Condo in Tavernier

4.99 out of 5 average rating, 102 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!

27 Sept – 4 Oct

$4,556 AUD total

Guest favourite

Apartment in Key Largo

4.92 out of 5 average rating, 232 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Enjoy gorgeous sunsets and excellent views of Manatee Bay from this beautifully upgraded studio apartment. The perfect spot for couples and small families, this modern studio comes with kayaks and paddle boards so you can get out on the water like a local. The ideal location offers easy access to the Bay, great restaurants, and local beaches. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park Experience Key Largo With Us & Learn More Below!

21 – 28 Nov

$2,483 AUD total

Guest favourite

Condo in Tavernier

4.98 out of 5 average rating, 142 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.

24 – 31 Mar

$4,461 AUD total