Nestled within the gated Truman Annex community in the heart of Old Town, this townhome boasts four separate outdoor spaces and lies just 100 feet from the pool. Bonus: An off-street parking spot is included!

Escape to this tranquil waterfront resort that lies just a few blocks away from Mallory Square. This two-bedroom unit at the Hyatt has a screened-in porch, lagoon pool and spa, and a white sandy beach. It also comes with complimentary parking, concierge services, and an in-room washer and dryer. For those with kiddos in tow, childcare, cribs, and high chairs are available upon request.

Stroll down to the lively Duval Street. Galleries and restaurants are also within walking distance. You can even charter a boat from the hotel’s dock. Limited boat slips are also available onsite. Sunday to Sunday rentals only.

Dubbed “McCartney’s Manor,” this cozy 350-square-foot studio has all the necessities: a bed, kitchen, and bathroom, plus a tiny two-person hot tub in its private gated courtyard. Share a pool with the other three rentals, all also named after members of The Beatles. There’s also a shared common area, bike rack, grill, and washer/dryer.

Don’t knock it till you’ve tried it! Stay on the water in Key West for a fraction of the price in this one-bedroom houseboat in Stock Island. It’s like staying in a floating camper. Sit on the covered patio off the front and watch for various fish, stingrays, crabs, starfish, octopus, lobsters, nurse sharks, and manatees. On the rooftop deck, enjoy great views of the bay and gorgeous sunsets, and watch for sea birds.

Miles of mangrove trails are yours to explore. Kayak or paddleboard up to grab some lunch at Cow Key Marina or Hurricane Hole.

This one-acre waterfront estate is situated on the Gulf of Mexico in Marathon, about 50 miles from Key West. Highlights include a pool, hot tub, volleyball court, and firepit. See amazing sunsets from the living room or out on the front porch.

This gated property also has a detached one-bedroom guesthouse to accommodate a total of 10 guests. The marina next door offers a place to dock your boat as well as lobstering and fishing gear. Walk to S.S. Wreck for some dreamy Key lime pie.

Nestled on 1.75 acres on the Gulf of Mexico in Marathon’s Grassy Key, this west-facing estate is pure paradise. It comes with a heated pool, tennis court, putting green, boat dockage, and lagoon! Bikes, a standup paddleboard, and a kayak are included. A concrete wall surrounds the premises with a gate to provide privacy.

Located on the southern tip of Long Key, this duplex is on one of the only private beaches in the Florida Keys. Take in spectacular views of the Atlantic Ocean from the beautiful deck, the tiki hut, or a kayak. Need more space? Rent the other side of the duplex, too!

A short walk up the beach, Long Key State Park offers camping, birdwatching, snorkeling, hiking, and canoeing. Shallow waters in front of the rental are perfect for cooling off, while a 30-foot channel allows boats to reach the dock. Boat rentals are available nearby.

This site once served as Henry Flagler’s Long Key Fishing Camp, a mecca for the world’s great saltwater anglers, and it’s still a great place to catch a tarpon.

It doesn’t get much better than this oceanfront estate set on three secluded, tropical acres in Islamorada. This four-bedroom house features a pool table, gym, tennis court, and a heated pool with an integrated jacuzzi. Watch the sun go down over the Atlantic from the dock.

A concierge service is included to make arrangements for whatever your heart desires, such as restaurant reservations, fishing or diving charters, and transportation. You can even pre-order groceries so the house is stocked with your favorite food and drinks when you arrive!

Wow! For an unforgettable vacation in the Florida Keys, rent this Dock View house on Mermaid’s Bay Estate. Set on three and a half acres, this waterfront home shares the property with two rented cottages. It also shares the walk-in pool, complete with a waterfall and hot tub. The property also features 300 feet of bayfront and a 190-foot dock. Swim and snorkel in the clear waters and take in spectacular sunset views.

Shops and restaurants aren’t far from this centrally located rental. Friday through Friday reservations are preferred.

Located on the Florida Bay in the secluded and intimate gated community of Coral Cove, this three-bedroom Islamorada vacation rental sleeps up to six adults. Not only does it have its own plunge pool, but there’s also a community bayfront pool. Two bicycles are provided, and a high chair and playpen are available upon request. There’s also a community dock if you want to bring a boat. Nightlife and restaurants can be found nearby.

About 90 minutes south of Miami and 90 minutes north of Key West near mile marker 76, this bungalow lies on the southern end of Islamorada. You can find it tucked away in a small, quiet community on the ocean side of Lower Matecumbe Key.

Take advantage of the shared heated pool and two cruiser bikes that are provided. Robbie’s Marina, restaurants, bars, marinas, and shopping centers are all within close proximity.

Located on Blackwater Sound in Key Largo, this two-bedroom condo is part of a gated community called Moon Bay. The complex offers several places to soak up the south Florida sun, including a beach, sundeck, hammocks, and pools. By the pool, there’s a clubhouse with foosball and ping pong. There’s also a sauna, tennis courts, a half basketball court, and shuffleboard.

Watch breathtaking Key Largo sunsets from the dock, which is also great for fishing and crabbing. Fishing poles, crab traps, tennis rackets, beach chairs, and two kayaks are included with the rental. A private boat slip is available for an additional fee. Reserved parking is right outside the building. There are also many restaurants nearby. Do note that the hosts prefer Saturday through Saturday bookings.