Vacation rentals with a pool in Sunset Key

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.

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

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.

Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock

Time to relax! Bring your family & friends to this 1200 sqft Waterfront home - Stay spacious in Key West. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grill, bike rentals, parking, secure keyless entry, & elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

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.

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Oct. & Nov. 50% off! Oceanfront, 4 Bikes 2 Kayaks

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

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

Windsor Townhomes #3

Welcome to Windsor Townhomes #3! Once you enter this beautifully decorated oasis…your vacation begins. This townhome has been created to meet your every need. The location is perfect; just three short blocks from Duval Street and tucked away on a quiet lane so you can choose your level of activity. The over 1700 square foot townhome is easily accessible to the action of Duval, and yet private and quiet for those wanting peace and tranquility.

*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.

106- Newly Renovated House with Oceanview and Pool

Sunrise Beach Resort gated community (11 homes, built 2007) 2 balconies, pool, dock, hammock, tropical landscaping Dock boats up to 25 ft; kayaks & paddleboards included 20 mins from Key West; near dining, Bahia Honda, Looe Key 2 master suites w/ king beds, en-suites & Smart TVs Open living/kitchen, BBQ, outdoor dining, parking for 3 Sleeps 6 w/ air mattress; Wi-Fi, streaming, towels provided No pets allowed

Duval St Apartment w/ Balcony w/parking Adult Only

This large apartment overlooks Duval Street from a private balcony. Perfect location in the heart of Old Town within easy walking distance of restaurants, live music, and historic sites. Guests enjoy daily complimentary continental breakfast in the garden and dips in our heated pool. *Please note you must be 21 or older to make a reservation on this property and all guests must be at least 18 years old.*