Vacation rentals with a pool in Key West

Sea Ray Cove w/ 80' Dock, Pool, Beach & Tiki Hut

2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Twin Dolphin Marathon Deep Water Canal, 100’ Yard!

Don’t miss this one! Dock your boat & relax in the swimspa pool at this deep water, canal home in Marathon’s Boot Key Harbour! Walking distance to ocean front tiki bars, restaurants and attractions! Quiet, residential street at MM 48.5, just off US 1, this one level home is in the heart of the Florida Keys. 2 queen bedrooms plus a sleeper sofa in the living area. With no neighbors on either side of the home, this is the ideal spot for personal space at our 100 foot wide lot. 2 kayaks provided!

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Bonaire Suite

The Bonaire Suite is a bi-level suite decorated in a rich contemporary palm tree motif with two queen beds separated by a privacy curtain in the upstairs bedroom. The upstairs bath features a custom tumbled marble shower with glass door. Downstairs is a living room with sofa that converts to a queen bed and a comfortable love seat. The large dining room easily seats six people. There also is a recently-installed half-bath on this floor for your convenience. Outside your door is a delightful,

Honeymoon Hideaway, King bed, Private Deck & Spa!

This Historic unit has Pale blue interiors, small efficiency kitchen, platform Pottery Barn King memory foam bed with multiple basket drawers underneath for storage, large shower. Large private deck with 2 person spa, hammock, outdoor sofa and table/chairs. Bose Bluetooth speaker, Alexa. Private gated compound and gated entrance to Honeymoon Hideaway. Renovated August, 2019 with new full bathroom and designer kitchen with dishwasher, 2 burner stove, refrigerator with freezer, microwave!

Grouper House: 4 Masters/6 BA, Pool/Dock, BoatRamp

Welcome to Grouper House, a stunning canal home w/ 4 Master Suites, King beds, private ensuite baths, in-room wine and coffee bars, smart TVs, and patio access. The open-concept kitchen/dining/living area includes a 55-inch smart TV and half bath. A covered porch overlooks a large saline pool w/ splash deck. Poolside is a shaded outdoor grill area w/ a sink, extra fridge, commercial icemaker, bait freezer, shower and 1/2 BA. The IPE dock has a fish-cleaning station and a private boat ramp.

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

Time to relax and unwind in this spacious 1,350 sq ft waterfront corner condo in historic Downtown Key West. Walk or bike everywhere—less than 1 mile to Duval Street, the Historic Seaport, and the Hemingway House. Enjoy a heated pool, tiki bar, BBQ grills, building elevator, and secure keyless entry. Please note: The condominium dock will be under construction beginning April 27, 2026 for approximately 30 days; dock access will be unavailable and daytime construction noise is expected.

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.

Amazing Ocean Front Views Key Colony Beach

Newly renovated studio condo in Key Colony Beach, Florida Keys. Unit #40 offers two queen beds, a full equipped kitchen with full-size appliances and essentials, reliable WiFi, and a SmartTV for a comfortable stay. Enjoy the heated pool and private sandy beach just steps away. Sunset Park is next door-perfect for catching a beautiful Florida Keys Sunset.

Vacation home Island Suite 16

The Island Suite is part of a historic Key West property built around 1889. Suite #16 is located on the first floor at the rear of the 411 William Street building. The Island Suite has one of the premiere locations in Old Town, Key West with lively Duval Street just 3 blocks away and the neighborhood boasting some of the finest older homes in Key West.