
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

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

A Great Escape! Private 2 Bed Rm Beautiful Marina
Our Marina has a pool and a small private beach overlooking the beautiful Keys water! More affordable than most places in Key West while able to reconnect with nature at this private getaway on the Great Escape. As you approach the boat, you feel your dream vacation has come true . One of a lifetime. Staying on a beautiful sportfisher yacht, laying in the waters of the calm keys and in the most beautiful peaceful marina, will definitely set you free from all your worries and stress.

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.

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.

Poolside Cottage #412
Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the seaport and world famous Duval Street! Bikes, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

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.

May 3+ Night Deal | Pool + Dock | Pet-Friendly
Time to relax and stay spacious in this 1,200 sq ft waterfront condo in Downtown Key West. Walk or bike everywhere - less than 1 mile to Duval Street, the Historic Seaport, and the Hemingway House. On-site amenities include a heated pool, tiki bar & grills, parking, secure keyless entry, & building elevator. Note: Dock access will be unavailable late April through May due to scheduled improvements; some daytime noise possible.

Castaway Cove: Pet-friendly 2/2 condo near beach!
Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.

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

Duval Vibes • Pool • 10 Guests

Gorgeous Romantic Private Villa, Steps from Duval!

Mango Cottage, a charming Key West home ready for

Beachfront Condo w/ Pool & Hot Tub | Papaya Place

Palm Breezes! Room for Everyone on the Ocean.

Waterfront Sanctuary in the Keys!

Your clean and cosy family home in Key West

Oceanfront, beach, heated pool, dock, tiki hut
Condo rentals with a pool

Condo de Paradise/Salt Water Pool/Boat Dock

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Shang-Ri-La at The Beach

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

EYW Getaway

Key Wes't Best- Upgraded condo 5 mins to Smathers

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

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

Sentient Waters: 63’ Boat With Full Amenities

43' Classic Yacht Views, Pools, Duval Shuttle

Luxury Boat Stay | Resort Amenities

Sunset Harbor 2 bed Ocean views!

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

TortugasHarbor Light Suite

Newly Renovated 2/2 Bath Condo, with shared pool

Waterfront Condo FREE Slip & Pool 2B2B in Key West
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 $181 AUD 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
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home & Museum
- Sunset Park
- Seven Mile Bridge
- Key West Lighthouse Museum
- Florida Keys Aquarium Encounters
- The Turtle Hospital
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- Boyd's Key West Campground
- Calusa Beach & Loggerhead Beach
- Boca Grande Key





