We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Florida Keys Vacation Rentals for Weddings

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $779 Average
    |||
    |||
    $0$1,000+
    Suitability
    Suitability
    More filters
    Travelers to Florida Keys are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    20 Matching Rentals in Florida KeysView all 1,543 rentals
    Sort by:
    Default
    Large Townhouse in Mariner's Club Resort - 3 BR/3.5 Bath1 / 26
    (5)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    7 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Patio
    • Grill
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you have your sights set on the ideal spot to spend your next tropical getaway, then jump on the chance to book your stay at this dog-friendly, oceanfront Islamorada home on a one-acre lot. Boasting a private stretch of white sand beach, a private pool, hot tub, and water toys like kayaks and...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    Make Inquiry
    Tee by the Sea - NO DAMAGE FROM HURRICANE IRMA , Plus 7 Bikes FREE1 / 30
    (67)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • DVD Player
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 25, 2017
    This lovely condo was great for our stay in Key West. Located on Stock Island just at the entry of Key West, it was perfect for staying "out of the frenzy" of town, but...
    Reviewed May 13, 2017
    We had a great three days on the island. Condo was well equipped although we ate out or got pizza - pizza place across the road served delicious pizzas. Ther were 5 of us so my...
    See all reviews
    About this property
    Very nice luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in very well maintained gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa with a 5' thick memory...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Private Yard
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in the beachside pool. The front home sits...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    Key Largo Rental Fantastic Views1 / 32
    (24)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • Ocean Views
    • Waterfront
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 23, 2018
    We had a great time at this condo. The owner is close by and extremely accommodating. He has gear for nearly every activity you can imagine, all for your use. The condo itself...
    Reviewed January 5, 2016
    Positive: complex was great with wonderful amenities..snorkeling, kayaking, pool, tennis, golf cart. Norman was very nice and went overboard to provide anything we asked for...
    See all reviews
    About this property
    Experience the relaxed lifestyle of the Florida Keys. 3 Bedrooms + Loft, 2 Baths, Sleeps up to 8 comfortably. There are 2 large bedrooms on the 3rd floor, each with queen size beds. The first floor bedroom is small with 2 bunk beds. The 4th floor loft is a general purpose room. Newly remodeled,...
    View all property information
    Location Information
    Key Largo, Florida Keys 33037
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Waterfront
    • Ocean Views
    • Washer
    • DVD Player
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your awe moment begins as you drive through the gates of the Moja Draga Estate, located on a beautiful 2 acre parcel of prime ocean front property in the village of Islamorada. Moja Draga is where your vacation dreams begin. Your island vacation home is well appointed with all that you need for a...
    View all property information
    Location Information
    Islamorada, Florida Keys 33070
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    Make Inquiry
    Save time - get the best Florida Keys rentals sent straight to your email!
    Get the List
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Washer
    • DVD Player
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Main House, a fully furnished 2-bedroom split-level house facing the bay. Features include private patio and barbecue, two dining areas and a large living room. The masters bedroom located at the top of the stairs contains 2 queen size, large closet, and an adjoining bathroom. The neighboring...
    View all property information
    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Make Inquiry
    Bayside Retreat. Pool, Boat and Beach1 / 13
    (4)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Porch
    • Washer
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 26, 2016
    We rented both of the houses for two weeks in June 2016. The houses were large and the views were great. Although the furnishings were sparse, and the televisions small, the...
    Reviewed January 21, 2014
    We needed space for 10 adults who were willing to share beds. This place was perfect. The stacking condos was a good idea and there was enough space in the top condo for...
    See all reviews
    About this property
    Island style, waterfront home with exclusive private white sand beach, A pool and protected dockage. 10 bedrooms, 8 bathrooms should be enough room for any size group.4 Living Rooms, Dining Room, Kitchen all have unsurpassed views of the open water and Sunset. On the first level is the pool. This...
    View all property information
    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Inquiry
    Banana Key1 / 25
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Terrace
    • Air Conditioning
    • Washer
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 20, 2018
    Really nice space. I would rent again. Great location. Clean, you can easily have 4 people in this property.
    Reviewed July 25, 2018
    Banana Key is the perfect place to stay in Key West for 2 couples of a family of 4. Within walking distance to Duval St, piers, and a plethora of shops and restaurants. We never...
    See all reviews
    About this property
    Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can enjoy breathtaking views just...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Inquiry
    Alligator Reef Compound1 / 99
    (2)Excellent
    10 Bedrooms, 10 Bathrooms, Sleeps 28 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2018
    We stayed for a week the end of June, we rented all four houses which was perfect for our group of 22. We ranged in age from one to 68 and everyone had a blast!The pools are...
    Reviewed May 30, 2018
    We had a great time at Alligator Reef. The house is so well stocked. The view is breathtaking. And there is so much to do we never left the property. We kayaked, swam in the...
    See all reviews
    About this property
    Got a large group that wants to 'get away from it all'? Or do you need lots of space for a family reunion or wedding? This is the perfect solution! Terrific location, beautiful view, two private pools for you to enjoy... And since it's 4 separate homes, you aren't right on top of each other. Wide...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 10 Bedrooms, 10 Bathrooms, Sleeps 28
    Make Inquiry
    Private Beachfront -Perfect for Families and Events Historic Shadow Point Estate1 / 82
    (20)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 5, 2018
    I was so fortunate to visit Shadow Point for a second time. I just love the feeling of being in such a special place. It is old Florida at its best with all the modern...
    Reviewed April 29, 2018
    First visit to the Keys after Hurricane Irma and return visit to Historic Shadow Point since November 2015. Same group of friends enjoyed much better weather this time around...
    See all reviews
    About this property
    Why would anyone want to rent a house on a canal right next to other houses and no real place to swim when you could rent this private, secluded, stunning place surrounded on 3 sides by water? We have the most charming and spectacular and intimate property in Key Largo for your vacation rental....
    View all property information
    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 16
    Make Inquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Bow Channel Manor and step back in time to Old Florida! You'll find this plantation style home remeniscent of Florida past! Enjoy family-style vacationing on a private 4 acre parcel of land on Upper Sugarloaf Key. The grounds are like a playground. There is a full-size heated pool with...
    View all property information
    Location Information
    Sugarloaf, Florida Keys 33042
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    Southern Diversion Islamorada see our fall special1 / 29
    (7)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Cable/satellite TV
    • Parking
    • Outdoor Dining Area
    • Washer
    • Grill
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 18, 2015
    Our family of 13 people enjoyed a full week at this property. The house was amazing along with outstanding views. The property was well clean that includes the yard, pool and...
    Reviewed March 28, 2015
    I did not stay here but our friends did and we attended a wedding there and it was amazing. Beautiful place and very clean. I hope my kids get married there!
    See all reviews
    About this property
    This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat lift, Tiki hut on private beach, Heated pool and Wireless remote Internet. Southern Diversion has just been completely renovated. Brand new...
    View all property information
    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 16
    Make Inquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Pelican House, is a 3 bedroom, 2.5 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the cooler seasons),...
    View all property information
    Location Information
    Long Key, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute 2 bedroom, 2 bath home directly on the gulf with a great dock too! Amenities * Air Conditioning * Aquatic Encounters * Area Fitness Center * ATM/bank * Babysitter * Bait Freezer * BBQ Grillbird watching * Boondocks Miniature Golf * Cable TV * Ceiling Fans * Central Airchildren welcome *...
    View all property information
    Location Information
    Duck Key, Florida Keys 33050
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    Pavilion Villa ~ Weekly Rental1 / 20
    (8)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 21, 2016
    Stayed with friends and family place need work. A/C in bathroom terrible, none. Kitchen, family room in main house never stayed cool. it says 3 baths 1 is outside beside the...
    Reviewed August 17, 2015
    When we arrived the main house smelled very musty. I immediately cranked the AC units down to 73 to get some of the air dried out. The King bedroom never lost the musty smell...
    See all reviews
    About this property
    A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a half-block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    Florida Keys Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    72° 62°
    December
    72° 61°
    January
    72° 61°
    February
    73° 64°
    March

    Additional Florida Keys Info

    Go to map view
    • Local time: 08:24 PM (EST)
    List your property
    Owner log in