
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.

Tropical Heron Hideaway w/ Hot Tub + Pool
Welcome to our unique and charming Airbnb. This cozy retreat offers the perfect blend of comfort and style, featuring a private porch where you can relax and enjoy the island breeze. Take a dip in the refreshing pool or unwind in the private hot jacuzzi after a day of exploring. Enjoy cooking a delicious meal on the grill, and experience a peaceful stay in a one-of-a-kind space. Whether you're here to relax or explore, our home provides everything you need for an unforgettable Key West getaway!

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

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.

Waterfront Condo Dock Pool Near Duval St
Relax above it all in this spacious top-floor waterfront condo in downtown Key West, offering added privacy and sweeping marina views. Perfect for families and groups, enjoy a full kitchen, open living space, and private balcony. Dockage available with a fish cleaning station and ice maker, ideal for boating and fishing. Located about 1 mile from Duval Street, restaurants, and nightlife, and 10 minutes from EYW airport, with a heated pool, tiki area, BBQ grills, parking, and secure entry.

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.

Poolside Cottage #411
Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat 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, kayaks, paddle boards and golf carts can 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.

*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.

Family House, 2 K BR's, Private Spa/Deck, 2 pools.
The Historic Family House is decorated in a light, Caribbean motif. It is a Cigar Maker's Cottage from 1880's. 2 K memory foam beds upstairs w/32” Smart TV's, Q sleeper sofa (memory foam mattress) in LR with 75” Smart TV. Bose blue tooth speakers and Alexa's. 1/2 bath up, full bath down plus an outdoor private shower. Full kitchen! Perfect for Families! Private rear deck with new 6 person Jacuzzi. 2 heated pools!

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.

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.
Popular amenities for rentals with a pool near Smathers Beach
House rentals with a pool

Pool Access + Local Art • Walk to Southernmost

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

Gorgeous Romantic Private Villa, Steps from Duval!

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute

Palm Breezes! Room for Everyone on the Ocean.

Waterfront Sanctuary in the Keys!

Casa de Cuba:Beautiful home loaded with style and

Family Home 3-bedrooms/3-bathrooms
Condo rentals with a pool

4-Bed, 3-Bath Waterfront Condo at Bayfront Suites

Seas the Breeze – Poolside Condo Near the Beach

Condo de Paradise/Salt Water Pool/Boat Dock

Oceanfront 3 bed condo Ocean Edge w/ optional slip

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

EYW Getaway

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

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

Sentient Waters: 63’ Boat, Free Snorkel Gear, etc.

43' Classic Yacht Views, Pools, Duval Shuttle

Best Resort in Key West, 2BD/2BA

Key West Beach House

Waterfront Boat Stay + Resort Amenities

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

Newly Renovated 2/2 Bath Condo, with shared pool

Palm - Beach Houses Key West
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.ﺇ 477 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
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Southernmost Point
- Key West Butterfly & Nature Conservatory
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Key West Aquarium





