A dolphin swimming near a wooden dock and a tree branch in the water.

Find Hotels with a Pool in Grassy Key, FL

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Check availability on Grassy Key Hotels with a Pool

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Grassy Key hotels with a pool

A tropical resort with a swimming pool, palm trees, and a view of the ocean.
A beach view with palm trees, a hammock, and a chair by the water.
A kitchen with white cabinets, a microwave, and a dining area with a glass table and white chairs.
An aerial view of a resort with a swimming pool, palm trees, and a beach area.

1. Gulf View Waterfront Resort

Gulf View Waterfront Resort
Marathon
  • Heated waterfront pool beckons with warm water and sun loungers, creating a peaceful retreat with views of the gulf.
$94 nightly
$106 total
Oct 1 - Oct 2
Total with taxes and fees
Gulf View Waterfront Resort
A swimming pool with a hot tub, palm trees, and a building with a staircase.
A beach with lounge chairs and umbrellas, palm trees, and a building with balconies.
A table with breakfast items and a view of the beach.
A wooden deck with two chairs and a table, overlooking a beach with palm trees and the ocean.

2. Rainbow Bend Resort

Rainbow Bend Resort
Marathon
  • Float away in the turquoise pool with ocean views before retreating to the poolside hot tub at sunset.
$149 nightly
$168 total
Oct 1 - Oct 2
Total with taxes and fees
Rainbow Bend Resort
A pool area with palm trees and a view of the ocean.
An outdoor dining area with thatched roof, wooden tables, and bar stools, overlooking the ocean.
A wooden deck with a pool and chairs overlooking a beach with palm trees.
A beach with a wooden walkway leading to the water, palm trees, and a clear sky.

3. Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club
Marathon
  • Splash into paradise with 2 outdoor pools and oceanfront relaxation at this serene resort.
$214 nightly
$240 total
Oct 5 - Oct 6
Total with taxes and fees
Grassy Flats Resort & Beach Club
A balcony with a view of a body of water, a pool, and outdoor seating.
A bar area with a long counter, bar stools, and a view of the water.
A balcony with a view of the ocean, a round table, and two chairs.
An outdoor dining area with tables and chairs, overlooking a body of water.

4. Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys
Marathon
  • Float away in a paradise with two outdoor pools, poolside dining, and marina views.
$134 nightly
$151 total
Oct 7 - Oct 8
Total with taxes and fees
Fairfield Inn & Suites by Marriott Marathon Florida Keys
A pool area with lounge chairs, a thatched-roof structure, and a view of the ocean.
Three colorful drinks on a table with a thatched roof and outdoor seating.
A modern kitchen with a central island, various appliances, and hanging pendant lights.
A modern living room with a large sectional sofa, a flat-screen TV, and a view of the sea through large windows.

5. Hampton Inn Marathon - Florida Keys

Hampton Inn Marathon - Florida Keys
Marathon
  • Sip cocktails while floating away worries at this Florida Keys escape with a poolside bar and hot tub sanctuary.
$122 nightly
$137 total
Oct 8 - Oct 9
Total with taxes and fees
Hampton Inn Marathon - Florida Keys
A poolside area with lounge chairs and umbrellas, overlooking a clear blue sea.
A spacious living area with a view of the ocean, a balcony with a pool, and a staircase leading to another level.
A hotel with a pool, beachside view, and a pier.
A beach with a palm tree, clear blue water, and a bridge in the distance.

6. Glunz Ocean Beach Hotel & Resort

Glunz Ocean Beach Hotel & Resort
Key Colony Beach
  • Serene coastal escapes await at this beachfront oasis with two sparkling pools and a hot tub for ultimate poolside relaxation.
$182 nightly
$199 total
Oct 18 - Oct 19
Total with taxes and fees
Glunz Ocean Beach Hotel & Resort
A pool area with lounge chairs and umbrellas, surrounded by palm trees.
A pathway leading to a pool area with palm trees and a sunset view.
An aerial view of a coastal resort with multiple white buildings, a clear turquoise sea, and lush greenery.
A covered outdoor area with a wooden deck, white railings, and a view of the ocean.

7. Hawks Cay Resort

Hawks Cay Resort
Marathon
  • Dive into paradise with 5 outdoor pools, private beach access, and poolside bars at this luxurious oceanfront retreat.
$255 nightly
$286 total
Oct 7 - Oct 8
Total with taxes and fees
Hawks Cay Resort
A pool area with lounge chairs, a wooden deck, and a view of the ocean.
A hotel room with a bed, a TV, a balcony with a view of the sea, and a table with chairs.
A beachfront property with a white balcony, palm trees, and a sandy beach.
A beach with clear blue water, a palm tree, and rocky outcrops.

8. Conch Key Fishing Lodge and Marina

Conch Key Fishing Lodge and Marina
Marathon
  • Tranquil waterfront retreat offers private beach, marina access, and pool oasis.
$83 nightly
$94 total
Oct 1 - Oct 2
Total with taxes and fees
Conch Key Fishing Lodge and Marina
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a white fence.
A two-story beachfront hotel with a wooden deck, palm trees, and a clear sky.
A marina with a dock, a boat, and a row of buildings with large windows.
A wooden deck with a covered area, green Adirondack chairs, and a view of palm trees and a water body.

9. Coconut Cay Resort & Marina

Coconut Cay Resort & Marina
Marathon
  • Poolside perfection awaits in this tropical marina escape with free water activities.
$91 nightly
$103 total
Oct 1 - Oct 2
Total with taxes and fees
Coconut Cay Resort & Marina
A swimming pool with yellow lounge chairs, palm trees, and a white building in the background.
A covered patio with a round table and chairs, large windows, and a view of a street and greenery.
A covered outdoor area with a view of a pool and palm trees.
A covered outdoor seating area with a round table and two chairs, overlooking a garden with palm trees.

10. Kingsail Resort

Kingsail Resort
Marathon
  • Sleek outdoor pool with marina views makes waterfront adventures a dream at Kingsail resort.
$81 nightly
$91 total
Oct 12 - Oct 13
Total with taxes and fees
Kingsail Resort
View all properties

Choose what matters most at hotels with a pool in Grassy Key

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Grassy Key Hotel Reviews

Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway

8/10 Good
"Room was clean and nice. Didn’t have alot of room in the bathroom, small sink no where to put things even in the shower. But overall great stay."
Jessica 3-night trip
Posted 1 hour ago
Captain Pips Marina & Hideaway
Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

10/10 Excellent
"Great"
Kevin 4-night trip
Posted 2 hours ago
Tranquility Bay Beachfront Hotel and Resort
Banana Bay Resort & Marina

Banana Bay Resort & Marina

10/10 Excellent
"Staff was nice and room clean"
Alexis 3-night trip
Posted 20 hours ago
Banana Bay Resort & Marina
Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Beautiful location, great amenities, and comfortable rooms"
Michael 7-night trip
Posted 22 hours ago
Lime Tree Bay Resort
Kingsail Resort

Kingsail Resort

10/10 Excellent
"wanda is the best, look for her , she is amazing"
Mileidis 2-night trip
Posted 2 days ago
Kingsail Resort
Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys

10/10 Excellent
"The property was meticulously clean. The staff was more than helpful if you needed something everyone was very kind. The only thing I object is the parking fee of $20 a day. I don’t see why we should pay $20 a day on their property when we’re staying there other than that, everything was fine. The buffet breakfast was really good. The food was hot and clean. The place was clean and my service dog was safe there if I had to leave them for a little while to do something, I wasn’t worried about it. I’m Social Security. It was very tight. I stayed there many times before I never had a problem."
Thomas 3-night trip
Posted 4 days ago
Fairfield Inn & Suites by Marriott Marathon Florida Keys
Skipjack Resort & Marina

Skipjack Resort & Marina

10/10 Excellent
"Great spot"
Justin 2-night trip
Posted 2 months ago
Skipjack Resort & Marina

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