Resort holiday rentals in Monroe County

4.87 out of 5 average rating, 97 reviews

Ultimate Getaway! Private Beach Access, Pools

LukeRating, 5 stars1 month ago

This resort was absolutely stunning, and we will definitely be visiting again! The beaches and pool were perfect and the Bakers Cay staff was unbelievably friendly and helpful throughout our entire trip. Both restaurants on site were also delicious and very conscientious of any allergies. I will say that since this particular Airbnb host is actually a third-party company, the communication was a little bit poor (they could not provide me with a confirmation number); however everything worked out great and the hotel had our room ready for us.

Orchid Suite

PET FRIENDLY up to 2 pets!! Unwind in this one bedroom suite located in the heart of Old Town Key West. This sun filled suite features a living room with a queen sleeper sofa, a kitchenette with a microwave\convection oven, a separate bedroom with king sized bed and a gated private outdoor area. Enjoy our complimentary breakfast, 3 pools, complimentary wifi, and smart TVs. Sleeps 4. We have very limited paid parking, first come first serve. *$25/pet per night, paid upon arrival to the property*

Enticing two Bedroom at Hyatt Sunset Harbor!

We are able to offer reservations in weekly increments with arrivals and departures on Fridays, Saturdays, and Sundays only. Discover a relaxing oasis overlooking the Gulf of Mexico in the heart of Old Town, steps from the shops, galleries, and cafes of Duval Street, and close to the nightly sunset celebration at Mallory Square. Hyatt Sunset Harbor’s spectacular gulf coast setting is matched only by the gracious service, top-tier amenities and meticulous attention to detail.

4.91 out of 5 average rating, 11 reviews

Parrot's Perch

The Parrot’s Perch (formerly Zeke’s Retreat) is a sun filled suite with soaring ceilings features a living room with a queen sleeper sofa, a wraparound porch with a hammock, a kitchenette with a convection \microwave oven and a bedroom with a king size bed with private balcony overlooking the palm trees. Sleeps 4 people. Complimentary breakfast included. Enjoy 3 pools, wifi, and smart TVs. Very limited paid parking available onsite on a first come first serve basis.

2BR Villa Hyatt Windward Pointe

2BR, 2Ba Villa (1065 sq ft) with full kitchen at 4-star Hyatt Windward Pointe Resort. Infinity-edge pool, outdoor grills, on-site restaurant and amenities. 1 BR has King bed, 2nd BR has queen bed. Each BR has attached full bathroom. Villa includes dining room, living room and furnished balcony with partial ocean view. Quiet location, 1.5 miles to popular Smathers beach, 5 miles to Mallory Square (with attractions, excursions, and nightlife).

4.82 out of 5 average rating, 17 reviews

Katie's Kottage

Relax in this private cottage located in the heart of Old Town Key West. The cottage sports 2 private bedrooms with queen beds, 2 bathrooms, a queen pullout couch, full living room and kitchen, & deck area that surrounds one of our pools. Enjoy our daily complimentary breakfast, 3 pools, wifi, and TV. Perfect for a group of up to 6 or families! We have paid parking first come first serve, or you can find free street parking.

Resort in Naval Air Station Key West

Oceans Edge Key West Resort, Hotel & Marina!

This stylish place to stay is perfect for group trips. This smoke-free hotel features a marina, 6 outdoor pools, and a restaurant. Additionally, a 24-hour fitness center, a bar/lounge, and a poolside bar are onsite. All 175 soundproofed rooms feature minibars and room service. Comforts include Egyptian cotton sheets and down comforters, and guests will also find conveniences like refrigerators and coffee makers.

A space that's all yours, with room for everyone

HVC The Beach House- your home away from home!

You'll enjoy your time at this cheerful getaway. The property has 3 floors with beautiful views. Suites come fully equipped with a kitchen, 2 BR, 2 BA. King beds in Brs and a double sleeper sofa in living area *PLEASE NOTE- Once you request specific dates, I reach out to Hyatt Vacation Club for availability. We own points, not a specfic unit. * A cleaning of $60 is due on checkout.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

Bungalows

Intimate homes, inviting architecture

Apartments

Convenient locations with everyday essentials

Popular amenities for Monroe County resort stays

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly Resort Stays

4.83 out of 5 average rating, 12 reviews

1BR Condo Banyan Tree, KeyWest Unit 505/701

JulieRating, 5 stars32 months ago

Fantastic location… walked everywhere! Enjoyed the pool and tiki area and the pathway, trees and foliage just gorgeous. I’m a sucker for a spiral staircase so loved the interior! We had everything we needed.

4.67 out of 5 average rating, 9 reviews

Studio#202CondoBanyan Tree Key West

MelissaRating, 5 stars34 months ago

WOW! I was so impressed with the amenities and the location of this place. I would most definitely try to stay here again the next time I come to Key West. Such a good location. So close to all the fun. A short bike ride away from EVERYTHING. The regulars at the resort were a blast too. Everyone was so nice and friendly.

4.67 out of 5 average rating, 6 reviews

Key Largo Cottages w/ Free Sailboat, Kayaks + More

NataliaRating, 5 stars52 months ago

This cottage is in an ideal spot in Key Largo. The amenities here are outstanding - two docks, snorkel gear, kayaks, stand-up paddle boards, and sailing! Great restaurants are within walking distance, too!

4.88 out of 5 average rating, 16 reviews

1BR #405 Banyan Resort Key West, FL

KimRating, 5 stars5 months ago

Great location! Enjoyed the beauty of the banyan trees.

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Resort rentals with a pool

Hotel room in Islamorada

2 Relaxing Garden View Suite | Beach Access

Hotel room in Islamorada

Relaxing Ocean Front Suite w/ Outdoor Pool

Hotel room in Islamorada

Beachside Stay w/ Private Beach + Garden View

Fleming's Veranda Townhome

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Resort rentals with a gym

4.83 out of 5 average rating, 12 reviews

Explore Key Largo! Beach Access, Pool, Parking!

BethanyRating, 5 stars14 months ago

The Key Largo location at Baker’s Cay is truly a gem! I would most definitely return in the future. There is so much to do and the resort is truly beautiful. I did not want to leave! The staff were also very friendly and helpful.

4.67 out of 5 average rating, 3 reviews

Studio - Hyatt Residence Club Key West

KatherineRating, 5 stars42 months ago

Great location and beautiful property! We’ll be back! Anthony was an excellent host!

4.82 out of 5 average rating, 11 reviews

Pool, Private Beach Access, Pet-friendly!

JanaRating, 5 stars1 month ago

The friendly and attentive staff really made our stay top tier. This is a beautiful place to relax and have fun.

Guest favourite

4.87 out of 5 average rating, 97 reviews

Ultimate Getaway! Private Beach Access, Pools

LukeRating, 5 stars1 month ago

This resort was absolutely stunning, and we will definitely be visiting again! The beaches and pool were perfect and the Bakers Cay staff was unbelievably friendly and helpful throughout our entire trip. Both restaurants on site were also delicious and very conscientious of any allergies. I will say that since this particular Airbnb host is actually a third-party company, the communication was a little bit poor (they could not provide me with a confirmation number); however everything worked out great and the hotel had our room ready for us.

4.82 out of 5 average rating, 50 reviews

Keys Escape! Close to Beach Road, Onsite Pool!

StacyRating, 5 stars4 months ago

We loved our stay at Bakers Cay. This is our 3rd time staying here, and booking with Victoria. The resort is beautiful. We loved being able to use kayaks and go fishing. We enjoyed restaurants in the area and a trip to the sandbar in Islamorada. We hope to come back again some time soon!