Holiday rentals in Summerland Key

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Top-rated holiday rentals in Summerland Key

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Superhost

Tiny home in Big Pine Key

4.85 out of 5 average rating, 130 reviews

Cheerful Tiny House in the Florida Keys

Enjoy your trip to the keys by staying at this wonderful tiny house, surrounded by nature and deers! This is a hidden gem in the keys for your relaxation, enjoyment. Cozy and roomy space for the whole family! The Tiny house is located in the small Breezy Pines RV Resort. It has everything you would need during your trip. Outdoor patio area with rattan sofa and armchairs, grill offer an additional comfort for incredible vacation! it has everything for your nice and comfy stay close to Key West!

Guest favourite

Home in Cudjoe Key

4.9 out of 5 average rating, 21 reviews

Rise & Shine

Spectacular sunrise view! Room to park one vehicle, but we do have a free overflow lot if needed. Community amenities include tennis, pickle ball, bocce ball, heated pool, hot tub, designated swim area, pool table, ping pong, & darts. We provide bedding, towels, pots & pans. TV in living room & one bedroom. We will also have boat bumpers installed all along the concrete dock that will accommodate a 40' boat. We offer 100% money back if your rental is in the projection cone of a named hurricane.

Superhost

Home in Cudjoe Key

4.92 out of 5 average rating, 37 reviews

Private Ocean Oasis by Key West, Florida

Beautiful stilted two bedroom/two bathroom vacation home awaits your arrival. Break taking views of the Atlantic Ocean are picture worthy. This home hosts a 36' seawall on a wide canal. Dock equipped with fishing cleaning station, cleats, swim ladder, outdoor shower and bait freezer. King-, queen-, full- and twin-size mattresses provide comfortable sleeping accommodations for all guests. Extensive indoor and outdoor furniture allow for all to relax, recharge and enjoy their time in paradise!!

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 193 reviews

Casa Mariposa: Easy walk to Sombrero Beach

***SUMMER SALE*** Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated by Forbes the #1 Airbnb for couples south of Orlando for 2024 and a top 10 Airbnb in Florida. Step from your private suite to our 50' chilled lap pool surrounded with swaying palm trees and tropical foliage, large coral stone patio, and extensive tropical gardens. Avoid beach parking fees at beautiful Sombrero Beach with a short stroll from your suite at Casa Mariposa!

Superhost

Home in Cudjoe Key

4.9 out of 5 average rating, 105 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Guest favourite

Guest house in Big Pine Key

4.83 out of 5 average rating, 12 reviews

Captain's Hideout

Peaceful Getaway. 1acre with picturesque views, this beautiful & cozy 1bedroom is perfect for those seeking solitude and nature. Key deer are frequent guests along with an Iguana, Box Turtle, Dolphins and sometimes a visit from the Manatees. Seagulls, Pelicans, White Ibis, Cormorant, and more beautiful birds will amuse you & add to the experience of a life time. The Ocean is 35 ft from your door with a boat house, cleaning station & private boat launch for the the avid fisherman as well.

Superhost

Home in Summerland Key

4.83 out of 5 average rating, 18 reviews

Waterfront Forever Summer house

MINIMUM STAY OF 28 DAYS REQUIRED TO BOOK.starts from 1st of each month. Pets consider $150 per stay. Waterfront house with heated pool. Located on the canal of Summerland Key, has a 60 ft dock. Easy access to both Atlantic and golf side!A spacious floor plan, carefully appointed furnishings, and great location.Open kitchen concept with quartz countertops, stainless steel appliances, and an eat in kitchen island, separate dining room.outdoor ice maker,freezer,smoker and grill.2 kayaks

Guest favourite

Cottage in Little Torch Key

4.9 out of 5 average rating, 154 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Superhost

Villa in Marathon

4.9 out of 5 average rating, 220 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Guest favourite

Home in Cudjoe Key

4.97 out of 5 average rating, 138 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Superhost

Home in Cudjoe Key

4.82 out of 5 average rating, 243 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Guest favourite

Rental unit in Key West

4.91 out of 5 average rating, 1,281 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, Mini Fridge, a microwave, Iron and iron board, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.