
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

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Ocean Front Studio private Sandy Beach in Key West
Studio unit with fridge, microwave, settings for 2 and a king sized bed. Doors that open to a balcony overlooking the Atlantic Ocean. There is pool, hot tub, and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street. The resort is located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. There is free garage parking with the room. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy air conditioning.

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

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.

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!

Waterfront Condo FREE Slip & Pool 2B2B in Key West
🌴 Key West Waterfront Paradise – FREE Dockage Included! Wake up to breathtaking marina views, unwind in the heated pool, and walk or bike to Duval Street in minutes. Enjoy a spacious condo with a private balcony, exclusive boat slip, and all the comforts you need for an unforgettable stay in the heart of Key West.
Popular amenities for rentals with a pool near Smathers Beach
House rentals with a pool

Gorgeous Romantic Private Villa, Steps from Duval!

Palm - Beach Houses Key West

Brisa Del Mar by AvantStay | Ocean Front Community

Funky Chicken Cottage with Shared Pool in Paradise

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

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Shang-Ri-La at The Beach

Waterfront Dock Pool Condo Near Duval St Pet OK

EYW Getaway

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

Orchid Bay Condo + Pool • Old Town • Walk to Duval

Henry's Piece of Paradise On The Ocean In Key West
Other vacation rentals with a pool

Sentient Waters: 63’ Boat With Full Amenities

43' Classic Yacht Views, Pools, Duval Shuttle

Best Resort in Key West, 2BD/2BA

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

Ocean~View w/ Dock, Pool, Kayaks, King Bed
Quick stats about rentals with a pool near Smathers Beach

Total vacation rentals
Explore 20 vacation rentals in Smathers Beach

Nightly prices starting at
Smathers Beach vacation rentals start at ﺩ.ﺇ477 per night before taxes and fees

Verified guest reviews
Over 120 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Smathers Beach vacation 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





