The 30 Best Holiday Rentals in Florida

Ranked 1 out of 26,101 in the Florida region, as well as being 1 of 732 for holiday rentals in Orlando.

• “Our first stay in Orlando”
• “”
• “Everything was perfect.”
• See more reviews of Roy's guest house

Ranked 2 out of 26,101 in the Florida region, as well as being 1 of 107 for holiday rentals in Key West.

• “Quiet.”
• “Heather and Scott were great / super nice and accommodating”
• “Perfect location, nice hosts, excellent service, comfortable...”
• See more reviews of Key West Villas

Ranked 3 out of 26,101 in the Florida region, as well as being 1 of 107 for holiday rentals in Pensacola Beach.

• “”
• “The location.”
• “Great view of the beach and Blue Angel airshow.”
• See more reviews of Pensacola, Oceanfront Paradise With Private Beach

Ranked 4 out of 26,101 in the Florida region, as well as being 1 of 231 for holiday rentals in St. Augustine.

• “We loved the decor and amenities.”
• “Lovely cosy bungalow in quiet location close to Historic centre”
• “Beyond our expectations”
• See more reviews of Luxurious Bohemian Bungalow in Lincolnville - Mins from Downtown!

Ranked 5 out of 26,101 in the Florida region, as well as being 1 of 19 for holiday rentals in Jensen Beach.

• “we had a great time staying at Ambers' place.”
• “Amber was an AMAZING HOST! She’s very attentive, kind, and we’re still in touch to plan our future stays! We can’t wait”
• “Beautiful home close to everything”
• See more reviews of Ambers Jensen Beachhouse with Hot Tub

Ranked 6 out of 26,101 in the Florida region, as well as being 2 of 231 for holiday rentals in St. Augustine.

• “Excellent home that was very clean and walking distance to everything.”
• “Beautiful home, fully stocked for anyone's stay”
• “”
• See more reviews of Weeden Cottage

Ranked 7 out of 26,101 in the Florida region, as well as being 1 of 688 for holiday rentals in Miami.

• “”
• “Perfect place to be for a trip to Miami.”
• “A lovely stay”
• See more reviews of Casa Cuba in Little Havana, Brickell, Calle 8 and 10 minutes to the Beach FREE PARKING

Ranked 8 out of 26,101 in the Florida region, as well as being 1 of 31 for holiday rentals in Port Charlotte.

• “”
• “Beautiful house and interior”
• “We loved everything about this place.”
• See more reviews of Lake Marlin Villa

Ranked 9 out of 26,101 in the Florida region, as well as being 1 of 9 for holiday rentals in Palm Beach Shores.

• “Beautiful property, in a great location!”
• “Design”
• “It was excellent, peaceful and fun.”
• See more reviews of Fernando Flats

Ranked 10 out of 26,101 in the Florida region, as well as being 1 of 38 for holiday rentals in Cape Canaveral.

• “We stayed 2 nights before leaving on a cruise and it was very convenient spot and hosts are great!”
• “Amazing place!!”
• “Perfect for a small group/family.”
• See more reviews of Sunny Delight I

Ranked 11 out of 26,101 in the Florida region, as well as being 2 of 732 for holiday rentals in Orlando.

• “Amazing, fantastic - will definitely return!!”
• “Stay here only if you love positive vibes!”
• “The host goes above and beyond to provide a spa-like...”
• See more reviews of La Maison De Lorbu - Apartment

Ranked 12 out of 26,101 in the Florida region, as well as being 3 of 732 for holiday rentals in Orlando.

• “Unfortunate”
• “Phenomenal accommodations!”
• “My family went to Disney and other parks and we did some...”
• See more reviews of New Spacious & Tranquil Townhouse near Disney - 4BR, 3FB, and Pool

Ranked 13 out of 26,101 in the Florida region, as well as being 1 of 113 for holiday rentals in West Palm Beach.

• “”
• “Convenient, comfortable and well equipped stay for families”
• “The best property and host you’ll ever find on booking.com”
• See more reviews of Beautiful Main House in West Palm Beach

Ranked 14 out of 26,101 in the Florida region, as well as being 1 of 139 for holiday rentals in Naples.

• “Absolutely perfect stay!”
• “”
• “I would highly recommend this property”
• See more reviews of Black Vanilla - Stylish Symphony 3miles Downtown

Ranked 15 out of 26,101 in the Florida region, as well as being 2 of 28 for holiday rentals in Homestead.

• “Very nice”
• “Very pretty cottage amid a beautiful garden.”
• “Nice little casita located on a fruit farm”
• See more reviews of Maria's Los Cirhuelos

Ranked 16 out of 26,101 in the Florida region, as well as being 1 of 342 for holiday rentals in Fort Lauderdale.

• “Absolutely amazing. Will be booking again.”
• “Exceptional”
• “A fabulous place 2 go on vacation”
• See more reviews of Casa806 Men Only Guest House

Ranked 17 out of 26,101 in the Florida region, as well as being 4 of 732 for holiday rentals in Orlando.

• “Comfortable”
• “Cute little house in a great location!!”
• “This was first experience with a tiny house and this was a...”
• See more reviews of Downtown Tiny Life - Experience Tiny Living!

Ranked 18 out of 26,101 in the Florida region, as well as being 2 of 44 for holiday rentals in Venice.

• “ABSOLUTELY will be staying again! Perfect location to the keys, perfect couples stay! LOVE LOVE LOVE!”
• “The property is located nearby to a bunch of restaurants,...”
• “It was overall a good stay but it had its downs.”
• See more reviews of Addy's Villas

Ranked 19 out of 26,101 in the Florida region, as well as being 3 of 38 for holiday rentals in Crystal River.

• “”
• “Great location”
• “was a cheerful, cozy cottage and our hostess was very helpful and flexible!”
• See more reviews of The Three Sisters - Pelican Crystal River FL

Ranked 20 out of 26,101 in the Florida region, as well as being 1 of 124 for holiday rentals in St Pete Beach.

• “We had our first apartment in St. Pete Beach. This was a nostalgia tour.🥰”
• “”
• “We will definitely go back. Nice quiet hotel and area-very close to the b each.”
• See more reviews of The Roth Hotel, Treasure Island, Florida

Ranked 21 out of 26,101 in the Florida region, as well as being 2 of 139 for holiday rentals in Naples.

• “”
• “Exceptional - next time we come to Naples, we hope the unit is available!”
• “It was a spectacular experience. The place was very clean and cozy. The most important thing for me was David's serv”
• See more reviews of Golf Condo- Resort Pool- LakeView- 10mi to beaches

Ranked 22 out of 26,101 in the Florida region, as well as being 2 of 688 for holiday rentals in Miami.

• “”
• “Cute and cozy place.”
• “”
• See more reviews of Miami's Cozy Tropical Getaway

Ranked 23 out of 26,101 in the Florida region, as well as being 1 of 773 for holiday rentals in Destin.

• “Perfect place for a family vacation!”
• “I will love to stay there again”
• “”
• See more reviews of 200 yds to private gated beach access- 3BR-2BA- quiet location in the heart of Destin!

Ranked 24 out of 26,101 in the Florida region, as well as being 3 of 688 for holiday rentals in Miami.

• “Very comfortable base in Miami.”
• “Perfect Miami Getaway: Your Ideal Home Base”
• “Exceptional experience!”
• See more reviews of Modern 2/1 Apt near Midtown and Beaches

Ranked 25 out of 26,101 in the Florida region, as well as being 1 of 421 for holiday rentals in Miami Beach.

• “”
• “We enjoyed our stay and highly recommend this beautiful house.”
• “Everything felt easy and breezy, just like Miami should.”
• See more reviews of NEW Amazing large 3BR direct oceanfront Penthouse On Ocean Drive!!

Ranked 26 out of 26,101 in the Florida region, as well as being 1 of 5 for holiday rentals in Rockledge.

• “Only there for about 15 hours, but would stay again and recommend to others!”
• “”
• “Pleasant and will definitely be back!”
• See more reviews of Shares View Luxury Apt

Ranked 27 out of 26,101 in the Florida region, as well as being 1 of 107 for holiday rentals in Bradenton.

• “Nice grounds pleasant neighbors. Much nicer than a hotel room”
• “I will stay here again , without hesitation.”
• “Very peaceful and worth the money”
• See more reviews of Cottage in Arbor Terrace Resort

Ranked 28 out of 26,101 in the Florida region, as well as being 2 of 342 for holiday rentals in Fort Lauderdale.

• “”
• “”
• “Very clean, and the location”
• See more reviews of Beach Aqualina Apartments

Ranked 29 out of 26,101 in the Florida region, as well as being 1 of 39 for holiday rentals in Gainesville.

• “”
• “Nice place but needs pest control”
• “Very nice, modern, clean house.”
• See more reviews of UF SUNSHINE HOUSE - Patio & BBQ - Chef Kitchen - EV Car Station - Upscale Neighborhood!

Ranked 30 out of 26,101 in the Florida region, as well as being 3 of 231 for holiday rentals in St. Augustine.

• “”
• “Beautiful memories were made.”
• “Great stay and convent and close to family”
• See more reviews of Relaxing Retreat and Modern Charm in Historic Saint Augustine