Vacation rentals in Summerland Key

4.94 out of 5 average rating, 163 reviews

A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.

Cottage in Cudjoe Key

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

4.96 out of 5 average rating, 108 reviews

The living room features a light-colored couch and love seat, complemented by decorative pillows. A coffee table sits in the center, and a Smart TV is mounted on the wall. Natural light is provided by the sliding glass doors, leading to an outdoor space.

Cottage in Cudjoe Key

Beautiful Cottage & Amenities in Gated Community

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

Tiny home in Big Pine Key

A coastal scene showcases palm trees swaying gently by the water. Thatched roofs provide shaded seating areas along the shoreline. Sailboats are visible on the horizon, amidst clear turquoise waters under a bright blue sky, with a few fluffy clouds drifting by.

4.89 out of 5 average rating, 102 reviews

Cottage 30 min from Key West, free parking, pool

Escape the everyday and unwind under the stars in this charming, nature-surrounded getaway where deer are frequent visitors. This cozy tiny house of offers 1 bedroom, 1 bathroom, and 3 beds, comfortably sleeping up to 4 guests. Enjoy peaceful surroundings, fresh air, and convenient double parking with space for a truck and boat trailer—perfect for outdoor adventures and total relaxation. Ideal for couples, families, or friends seeking quiet nights, wildlife views, and a simple, memorable stay!

A serene canal view during sunset, showcasing vibrant orange and pink hues reflecting off the water. A concrete dock extends into the water, equipped with a fish cleaning station. A table and chairs are positioned nearby for relaxation and enjoyment of the picturesque scene.

4.92 out of 5 average rating, 12 reviews

Blue Heaven Waterfront Home

Lobstering paradise 2 houses from open water, deep 60' canal, gorgeous water views, direct access to the Atlantic/Gulf, 35' dock/seawall. 3 zone mini split A/C and heat, overhead ceiling fans, fully stocked kitchen, microwave, washer/dryer, 42" Smart TV in living room and master bedroom, WIFI. King size bed in the master, queen bed in 2nd bedroom, and a queen sofa in the living room. Beach towels, linens. Marina store with bait & fuel onsite, 2 wide boat ramps, pool, hot tub & Rec center.

5 out of 5 average rating, 21 reviews

An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.

Condo in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

A scenic waterfront area is depicted with vibrant green lounge chairs positioned on a sandy peninsula. Surrounding waters provide a tranquil blue hue. Wooden docks extend into the bay, complemented by lush palm trees and colorful buildings in the background.

4.95 out of 5 average rating, 106 reviews

Waterfront Anchor House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Haven House to reserve both homes if available). 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 point and enjoy the underwater scenery!

Superhost

A comfortable outdoor seating area is showcased, with bright blue cushions arranged around a dark table. The view overlooks crystal-clear waters, and decorative lanterns provide soft lighting. A potted flower adds a touch of color beside the seating, enhancing the peaceful ambiance by the water.

4.88 out of 5 average rating, 130 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Tiny home in Summerland Key

4.96 out of 5 average rating, 26 reviews

Cottage

Experience island living at Sugarloaf RV Resort's NEW Cottages in the Lower Keys, just 25 minutes from Key West. These Two-Bedroom Cottages sleep up to 4 guests with 2 Queen beds. Features include a kitchenette with double burner stovetop, dorm fridge, microwave, single serve coffee maker, toaster, plus outdoor seating. Coastal charm with keys-style design and a private patio perfect for morning coffee or sunset relaxation.

A serene outdoor space features palm trees swaying gently by the water's edge, with a small floating dock visible. Loungers are arranged by the pool, surrounded by pebbled landscaping and lush greenery, all under a clear blue sky.

4.9 out of 5 average rating, 39 reviews

White House - Receive $400 towards a Boat Rental!

Receive a $400 gift certificate towards a boat rental. When you reserve a week for any of the dates and house below. When you book a full week at one of our homes staying between the dates of Sept 1, 2026 through Dec 19, 2026 Except for Nov 21-28, 2026 Please reach out before booking for boat availability. Kayaks come with the rental. Small floating dock for your boat.

A boat is docked at a private marina, showcasing a spacious outdoor area. A fish cleaning station is visible nearby, along with a hose and power source. Colorful buildings line the waterfront, and clear blue skies reflect over the water.

5 out of 5 average rating, 10 reviews

35’ dock/Completely Remodeled VO 366

Dock your boat and enjoy open water views. Our 2 bedroom 2 bathroom newly remodeled home is perfect for your family get away or a couples retreat. Home comes with 2 kayaks and 2 bikes. The gated community offers pool, beach area, hot tub, pickle ball, playground area, basketball and a recreation room. THERE IS A $125 RESORT FEE DUE AT THE GATE UPON ENTRY.

Top guest favorite

The Tiki Suite is presented on a wooden platform, showcasing thatched roofing and an inviting porch area. Two stand-up paddleboards are placed alongside the structure, with calm waters reflecting the clear sky.

Houseboat in Key West

4.91 out of 5 average rating, 527 reviews

Tiki Suites ~ Original Tiki ~ Private Water Stay

Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.

4.85 out of 5 average rating, 13 reviews

Home in Key West

KW Beach house with heated pool, dock, accessible

This is a minimum 28 night minimum rental. Welcome to your dream getaway, just 13 miles from downtown Key West! This charming two-level beach home offers the perfect blend of relaxation, adventure, and luxury. With accommodations for up to 10 guests, bring the entire family, friends, and even your fur babies, and don’t forget your boat!

Popular amenities for Summerland Key vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Summerland Key

An aerial view of the cottage surrounded by lush greenery and the calm waters of a mangrove area. The property features a spacious driveway leading to the home, with natural landscapes extending towards the Gulf of Mexico in the background.

4.8 out of 5 average rating, 79 reviews

Kelly’s Kabin - Private FL Keys Cottage

A serene sunset view is captured from a wooden dock extending over calm waters. Silhouetted figures can be seen seated at the end of the dock, with vibrant orange and purple hues reflecting off the surface. Framed by natural foliage, the scene offers a peaceful atmosphere.

4.86 out of 5 average rating, 42 reviews

Powell Family Resort

A vibrant sunset casts warm hues over the water, creating a mirror-like reflection. A wooden dock extends into the foreground, leading to the horizon, surrounded by silhouettes of trees along the shoreline. Outdoor seating is visible near the water's edge.

4.57 out of 5 average rating, 100 reviews

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

Top guest favorite

An aerial view showcases a coastal community with a spacious beach area, palm trees, and turquoise waters. The two-story unit features a large balcony above the entrance, with the surrounding buildings and lagoon clearly visible, highlighting the vibrant landscape of the area.

4.97 out of 5 average rating, 191 reviews

Cudjoe Key Home with a View

Top guest favorite

4.94 out of 5 average rating, 17 reviews

Starlight Serenity - Hideaway with Stunning Views

Superhost

A sandy beach area is framed by swaying palm trees, leading to a two-story bungalow elevated on stilts. Lounge chairs are arranged on the shore, providing a relaxing spot, while kayaks are visible in the background, enhancing the inviting beach setting.

Home in Upper Sugarloaf Key

4.75 out of 5 average rating, 103 reviews

Palm - Beach Houses Key West

A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.

4.81 out of 5 average rating, 307 reviews

APRIL $Save $ Oceanfront 4 BIKES/2Kayaks. KING bed

The exterior of a yellow house is shown with multiple windows providing natural light. A bike stands parked on the gravel beside a garden featuring tropical plants. Stairs lead to the entrance, and the surrounding area is landscaped with pebbles.