
Beachfront rentals near Smathers Beach
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Top-rated beachfront rentals near Smathers Beach
Guests agree: these stays are highly rated for location, cleanliness and more.

ATLANTIS...Ocean Front Cottage Retreat!
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

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.

Powell Family Resort
Tranquility abounds in this unique property with fantastic sunset views, beach and a superior pool. Total privacy is yours, deep water dockage abounds on this 2.5 acre estate.. Outdoor gas grill , kayak's and paddle boards included, Tiki Bar. Master bedroom with whirlpool tub, enclosed porches, newly remodeled kitchen. A great place to gather for a large group of family time or friends. Contact for rentals less or over a weekly stay when available. May 30-June 6 available and 2 weeks in Aug.

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS
AWESOME VIEWS 3 BEDROOMS/2 BATHROOMS/KITCHEN/LAUNDRY ROOM/SCREEN PORCH/SUN PORCH GREAT SNORKELING UNDER DOCK./FISH FROM DOCK TOO. GROCERY (WIN DIXIE) LOCATED 3 MINUTES AWAY/BIG PINE Snorkel or dive at Looe Key coral reef, ride bicycle through Key Deer country, or take fishing adventure in back country or troll deep blue waters beyond the reef. Explore National Key Deer Refuge, large expanse of mostly undeveloped pine lands where the diminutive Key Deer live, or venture out to the "wetlands"

Oceanside home 111, dock,kayaks,bikes,pool,fishing
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #111 and I also rent adjacent homes 109 and 107 in case you need more than one. We are 40 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

Family Suite at Sugarloaf Key Hotel (Pet Friendly)
Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

Oceanfront Key West Condo
Discover the charm and grace of Old Key West in a new and distinctive setting. Luxury, two-bedroom, two-bath, waterfront condominium set in a tropical garden paradise with sweeping balconies overlooking the Atlantic Ocean. Your vacation hideaway is decorated in authentic island tradition with fully-equipped modern kitchen, living room with wet bar, and dining room. Washer/dryer, phone, TVs, stereo, and over-sized jacuzzi tub in the master suite.

Key West Condo with Balcony Ocean View
Enjoy beautiful views of the Atlantic Ocean while enjoying a private balcony. Newly re-modeled kitchen. Air conditioning and ceiling fans located in every room. Amenities include pool, hot tub, and tennis courts. Just a few steps across the street in Smathers Beach which offers beach chairs, umbrellas, paddle boards, kayaks and sailboats available for rent. Two vehicles max. NO TRAILERS of any kind allowed to park on property.

Hyatt Windward Pointe Resort: Beachfront Condo
Experience this tropical paradise as you relax in a family friendly timeshare within the Hyatt Residence Club. Have breakfast on the oceanfront balcony followed by a dip in the pool/hot tub or visit the nearby spa. There are 2 bedrooms and 1 sofa bed which can fit 6 people. 2 bathrooms with a spa tub in master bedroom. Fully functioning kitchen and dining area in addition to an in-home washer/dryer unit.

Blue Palms Retreat
This 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key private heated salt water swimming pool, shaded hang out area, ping pong table, corn hole game. The pier, gazebo, kayaks and kayak launch area is shared with one other home, Latitudes. You can dock your 24' boat at the pier. The water is shallow getting out to the channel with about a 2' draft.

Galleon Resort - Walk to Duval & Mallory Square!
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach, pool, jacuzzi, with a restaurant and bar. Relax in the Jacuzzi or sauna during your stay or work out in the onsite fitness center. Enjoy fishing off the dock, or rent bicycles and take in all that Old Town Key West has to offer.

Oceanfront, beach, heated pool, dock, tiki hut
This is a minimum 28 night minimum rental. Welcome to your dream getaway, just 13 miles from downtown Key West! This charming two-level beach home offers the perfect blend of relaxation, adventure, and luxury. With accommodations for up to 10 guests, bring the entire family, friends, and even your fur babies, and don’t forget your boat!
Popular amenities for beachfront rentals near Smathers Beach
Pet-friendly beachfront home rentals

Traditional 2 Queen, The Pier House, Beach Access

Pure Wellness Spa Jr Suite, The Pier House Resort

RV In The Keys | Tropical Retreat

Relaxing Ocean View Stay! Pool & Onsite Dining!

Serene Resort w/ Private Beach & Spa in Key West

Seaside Getaway! Gym, Spa, Pool Harbor Access

Family Retreat

Calypso Cottage
Beachfront home rentals with a pool

Ocean Front Studio private Sandy Beach in Key West

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Ocean front 1BR/1BA Suite w/ kitchen & living rm

Oceanside home 111, dock,kayaks,bikes,pool,fishing

Affordable Beachfront Luxury Condo Sleeps 6

Oceanfront, beach, heated pool, dock, tiki hut

Oceanside home 109, dock,kayaks,bikes,pool,fishing

Tropical Paradise Resort Near Southernmost Point
Private beachfront home rentals

Beach House Resort + Premium Amenities, 2BR Condo

Key West ocean front Resort w/private sandy beach

Key West paradise- 3 night stay Minimum

Ocean front 1BR/1BA Suite w/ kitchen & living rm

Galleon-Walk to Duval & Mallory Square!

Beach House Retreat + Premium Amenities, 2BR Condo

Hyatt Beach House-Quiet Key West Spot!

Private Beach House Resort Oasis, 2-Bedroom Suite
Luxury beachfront home rentals

Key West Perfect Family Vacation! Pets Allowed

Lanai Two Queen, The Pier House, Beach Access

Oceanfront 2Q, The Pier House, Private Beach, Pets

Island-Style Resort Perfect for Beach Getaways

WATERFRONT GALLEON BEACH & MARINA, 2BR+Amenities
Quick stats about beachfront rentals near Smathers Beach

Nightly prices starting at
Smathers Beach holiday rentals start at $165 SGD per night before taxes and fees

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

4.6 Average rating
Smathers Beach stays receive an average rating of 4.6 out of 5 from guests
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
- Southernmost Point
- Key West Butterfly & Nature Conservatory
- Boyd's Key West Campground
- Calusa Beach & Loggerhead Beach
- Boca Grande Key





