
Home rentals with a pool near Smathers Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool near Smathers Beach
Guests agree: these stays are highly rated for location, cleanliness and more.

Fully renovated 2/2 bath condo w/ shared pool!
**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

Dock Pool Downtown Duval Pet-Friendly Waterfront
Relax and unwind in this spacious 1,200 sq ft waterfront condo in downtown Key West. Perfect for families and groups, enjoy a full kitchen, open living space, and a private balcony overlooking the marina. Dockage available with a fish cleaning station and ice maker, ideal for boating & fishing. Located about 1 mile from Duval Street, restaurants, and nightlife, and just 10 minutes from EYW airport. Amenities include a heated pool, tiki area, BBQ grills, free parking, elevator, and secure entry.

Charming Key West Vacation Rental 3bedrm/3bath
Beautiful gated home located in Coral Hammock just minutes away from Key West. It's a spacious 3 bedroom, 3 bath home with a full kitchen, living room, indoor and outdoor dining. With access to shared pool, club house and gym. Everything you need to enjoy vacation. We have also updated the unit with new flooring throughout! Beach Gear is also available Beach towels, beach chairs, beach toys, floats and cooler. Baby / Toddler. Portable Crib, high chair & more. Items available upon request

Gorgeous Ocean View in Paradise, Close to Key West
This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

KW Luxury 2/2 Beachfront resort Tropical Oasis
1357 s f Luxury beachfront resort condo w/ all the amenities - beachfront heated Olympic pool, 3 lighted tennis courts, 20 man hot tub, tropical gardens, beach, saunas, Gym, BBQ Grills everything to make your vacation spectacular! You must be at least 25 years old to rent this property. This is a no animal rental due to extreme allergies of the owner. Thank you for understanding. Spalling work hs begun on the balconies of the other building this may impact your enjoyment of the pool

Penthouse in Paradise
Coconut Mallory is a waterfront private community that provides resort amenities. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also a Jacuzzi and a picnic area with BBQs for guest use. This unit is a two bedroom two bath. It also features two off street parking spaces included. *The Master Tub is not to be used per the community as leaks have occurred in other units before.

The Lighthouse - Beach Houses Key West
If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

Tropical Old Town Bungalow
Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

Tropical Escape at Sunrise
We thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, basic cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests. Must be 25 and older.

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Paradise found
Located on Stock Island this 3 bedroom home is only 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large resort style swimming pool. Queen bedroom on first floor with full bath. Second floor King room with private full bath. 3rd bedroom as two twin beds beds with private full bath.

Affordable Beachfront Luxury Condo Sleeps 6
My place sits on Smather's beach! Close to downtown and the airport. You’ll love the condo because of the location, the large indoor space, it's quiet, the pool, and has all the comforts of home. My condo is good for couples, solo adventurers, business travelers, families (with kids), and big groups. It’s spacious - and very clean!
Popular amenities for rentals with a pool near Smathers Beach
House rentals with a pool

Gorgeous Romantic Private Villa, Steps from Duval!

KW CanalFront 3BR: Htd Pool, Boat Tie-Up, Pet OK

White House - Receive $400 towards a Boat Rental!

Beachfront Condo w/ Pool & Hot Tub | Papaya Place

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Palm Breezes! Room for Everyone on the Ocean.

Waterfront Sanctuary in the Keys!

Your clean and cosy family home in Key West
Condo rentals with a pool

Oceanfront 3 bed condo Ocean Edge w/ optional slip

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Shang-Ri-La at The Beach

Key West at Hyatt Windward Pointe

EYW Getaway

Sunrise Suites Resort, Key West FL U #408 2bdr2bth

Orchid Bay Condo + Pool • Old Town • Walk to Duval
Other holiday rentals with a pool

43' Classic Yacht Views, Pools, Duval Shuttle

Castaway Cove: Pet-friendly 2/2 condo near beach!

Best Resort in Key West, 2BD/2BA

Sunset Harbor 2 bed Ocean views!

Luxury Boat Stay | Resort Amenities

3BR In Resort Village, Pools, Free Kayak & Shuttle

Newly Renovated 2/2 Bath Condo, with shared pool

Luxurious 40' Sailing Yacht!
Quick stats about rentals with a pool near Smathers Beach

Total holiday rentals
Explore 20 holiday rentals in Smathers Beach

Nightly prices starting at
Smathers Beach holiday rentals start at $222 NZD per night before taxes and fees

Verified guest reviews
Over 120 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Smathers Beach holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Smathers Beach rentals

4.9 Average rating
Smathers Beach stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Sombrero Beach
- Long Beach
- Bahia Honda State Park
- Sunset Park
- Ernest Hemingway Home & Museum
- Fort Zachary Taylor Historic State Park
- Seven Mile Bridge
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Key West Lighthouse Museum
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- Boyd's Key West Campground
- Calusa Beach & Loggerhead Beach
- Boca Grande Key





